Month: May 2021

Application of 36947-68-9, These common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example A29 A mixture of 2-isopropylimidazole (3.0 g, 27.2 mmol) and DIEA (5.28 g, 40.9 mmol) in DCM (75 mL) was treated drop-wise with methoxyethoxymethyl chloride [MEM-Cl](4.24 g, 34.0 mmol) and stirred at RT for 16 h. The mixture was washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 2-isopropyl-1-((2-methoxyethoxy)methyl)-1H-imidazole (3.91 g, 72%). 1H NMR (400 MHz, DMSO-d6): delta 7.11 (d, J=1.3 Hz, 1H), 6.74 (d, J=1.3 Hz, 1H), 5.30 (s, 2H), 3.47-3.46 (m, 2H), 3.38-3.37 (m, 2H), 3.19 (s, 3H), 3.08-3.07 (m, 1H), 1.18 (d, J=6.8 Hz, 6H).

Statistics shows that 2-Isopropyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 36947-68-9.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-88-1, These common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step C – Methyl 5-{5-bromo-1 A£benztmidazoi-1-yl)-3-{[f°/£ butyl{dimethyi)si.yl]oxy}thlophene-2-carboxyiate and methyl 5-(6-bromo1 H- be?zimldazo.-1-yl)-3″{[/erf”btyf(dimethyi)silyl]oxy}thiophene-2-carboxy.ate {title compounds)To a solution of crude, impure 5-bromobe?zimidazo.e (48.2 g) and methyl 2- chioro-3-oxo-2,3-dihydrothiophene-2-carboxylate (42 g, 220 mmol) In 800 mL of CHCl3 was added Mmethyiimidazote (28 rrsL, 350 mmol). After 16 h, N- roethyl imidazole (17 mL, 220 mmol) and (38 g, 240 mmoi) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto ceiite. The crude mixture was purified by flash column chromatography (Q- 25% EtOAc:hexa?es) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 4 eluiing first and 29.2 g of Intermediate 5 elupsilonti?g second (58%), (Intermediate 4, 5~thetar) 1H NMR (400 MHz, drthetayUSDG) delta 8.77 (s, 1H)1 8.01 (d J – 1.6 Hz, IH), 7.76 (d, J -8.8 Hz1 IH)1 7.56{dd, J ^8.8 and 1.6 Hz5 1 H)1 7.25 (s, 1 H), 3.76 (s, 3H)1 0.99 {s, 9H), 0.27 (ss 6H). (trfermediate 5, 6- Br) 1H NyR (400 MHz1 (J6-DMSO) delta 8.71 (S1 1H), 7.88 (d, ./ – 1 ,6 Hz, 1H), 7,73 (d, J ^ 8.8 Hz5 I H), 7.50 (, ./=8.8 and 2.0 Hz1 I H)1 7.28 (s, 1H)1 3.77 (s, 3H), 0.99 (s, 9H), 0.26 (s, 6H).

Statistics shows that 5-Bromo-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 4887-88-1.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 496-46-8, These common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A steel autoclave (25 cm3) was charged with 2, 3 or 5 (2.5 mmol), filled with liquid CO2 to a pressure of 60 barand cooled to 5 C. Then nitrating agent (5.5-10.0 mmol, see Table 1)dissolved in liquid CO2 (~3.5 g) was added in ten steps for 15 min. Thereaction mixture was gradually warmed to room temperature and stirredfor 2 h at 80 bar [for supercritical conditions (Table 1, entry 8), the temperatureand the pressure were raised to 45 C and 100 bar, respectively,after the addition of the nitrating agent]. After 2 h stirring, the ice water(2 ml) was pressurized into the autoclave to destroy the access of nitratingagent. The CO2 was removed and additional amount of ice water (20 ml)was added to the residue at atmospheric pressure. The precipitate wasfiltered and dried at 40 C for 2 h to afford nitration product 1, 4 or 6, respectively. Isolated yields are given in Table 1. The NMR spectra ofknown compounds 1a,2 1b14 and 615 correspond to reported data. Meltingpoints of compounds 1a-c and 4 were not observed. Temperatures TID atwhich originally colorless solids started to become dark (initiation of adecomposition) are given below.1,4-Dinitroglycoluril 1a: TID 192 C. 1H NMR, d: 6.03 (s, 2 H, CH),9.83 (s, 2 H, NH). 13C NMR, d: 149.0, 63.8. 14N NMR, d: -39.5.3a,6a-Dimethyl-1,4-dinitrotetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione 1b: TID 194 C. 1H NMR, d: 1.82 (s, 6 H, Me), 9.94 (s, 2 H, NH).13C NMR, d: 146.5, 76.9, 17.8. 14N NMR, d: -46.6.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zharkov, Mikhail N.; Kuchurov, Ilya V.; Fomenkov, Igor V.; Zlotin, Sergei G.; Tartakovsky, Vladimir A.; Mendeleev Communications; vol. 25; 1; (2015); p. 15 – 16;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The ethyl 1-(4-cyanomethyl-1-oxoindan-2yl)imidazole-2-carboxylate can be obtained in the following manner: a solution of 1.8 g of ethyl imidazole-2-carboxylate in 30 ml of acetone is supplemented with 8.6 g of potassium carbonate. This suspension is heated at reflux for 15 minutes and then a solution of 3.22 g of 2-bromo-4-(cyanomethyl)indan-1-one in 30 ml of acetone is added. After stirring for 4 hours at reflux temperature, the reaction medium is brought to a temperature close to 20° C. and filtered on sintered glass. The filtrate is evaporated and 2.7 g of a black solid are obtained. The purification by flash chromatography on a silica column (eluent: dichloromethane-ethyl acetate (50-50 by volume)) of this solid gives 0.62 g of ethyl 1-(4-cyanomethyl-1-oxoindan-2-yl)imidazole-2-carboxylate in the form of a brown solid [mass spectrum m/z 309 (M+), 236 ((M-CO2 Et), +), 141 ((C6 H9 N2)+), 68((C3 H4)+)].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; Rhone Poulenc Rorer S.A.; US5990108; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 1 -methyl- lH-imidazole-4-carbaldehyde (lg, 9.1 mmol, 1.1 eq.) in THF (12 mL) is added P(Bu)3 (2.16 mL, 8.7 mmol, 1.05 eq.) and the reaction mixture is heated at 50C for 5 min. teri-butyl ester acrylate (1.2 mL, 8.3 mmol, 1 eq.) is added and the reaction mixture is stirred at 80C for 3h. teri-butyl ester acrylate (0.3 mL, 0.25 eq.) is added and this process (heating 3h and addition of tert- butyl ester acrylate) is repeated until no evolution is observed by TLC (EtOAc) and UPLC/MS. The reaction mixture is concentrated in vacuo and the residue is purified by flash chromatography on silica gel (eluting with Heptane/EtOAc 100/0 to 0/100) to afford the expected product. LCMS: MW (calcd): 238; m/z MW (obsd): 239 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; BREBION, Franck, Laurent; ALVEY, Luke, Jonathan; AMANTINI, David; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene, Marie; PEIXOTO, Christophe; VARIN, Marie, Laurence, Claire; DE CEUNINCK, Frederic, Andre; POP-BOTEZ, Iuliana, Ecaterina; (317 pag.)WO2016/102347; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 4.08 g (20 mmol) compound 2 in glacial acetic acid (30 mL) wasadded dropwise to 45 % aqueous sodium nitrite solution (10 mL, 65 mmol) at0-5 8C under a nitrogen atmosphere. The reaction mixture was stirred at 20 8C for2 h then poured into ice-water and neutralized with saturated sodium carbonatesolution. The precipitate was isolated by filtration, washed with water, and vacuumdried. The solid obtained was recrystallized from methanol-diethyl ether (2:1 v/v) togive compound 3 (3.34 g; yield 72 %) as pale yellow crystals, m.p. 152.3-153.9 8C. 1H NMR (400 MHz, CDCl3) d: 1.44-1.49 (t, J = 7.2 Hz, 3H, CH3), 4.47-4.53 (q,J = 7.2 Hz, 2H, CH2), 7.26-7.69 (m, 4H, ArH), 11.06 (s, 1H, OH). IR (KBr) m(cm-1): 3416 (N-H), 3258 (O-H), 3070 (Ar-H), 1714 (C=O), 1622 (C=N), 1279,1043 (C(O)-O-C). ESI-MS m/z: calcd for C11H11N3O3 [M ? Na]? 256.2, obsd[M ? H]? 256.4.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Peizhi; Wan, Fuxian; Li, Ying; Li, Chengkun; Jiang, Lin; Research on Chemical Intermediates; vol. 41; 6; (2015); p. 3349 – 3357;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H7BrN2

A mixture of 5-bromo-l-methyl-li7-benzo[7]imidazole (302.3 mg, 1.432 mmol), diphenylmethanimine (341.5 mg, 1.885 mmol), t-BuONa (271.1 mg, 2.821 mmol), BINAP (89.7 mg, 0.144 mmol) and Pd2(dba)3 (130.6 mg, 0.1426 mmol) in l,4-dioxane (10 mL) was heated to 100 C and stirred overnight under N2 atmosphere and then concentrated in vacuo. The residue was diluted with water (40 mL) and the resulting mixture was extracted with a mixed solvent of DCM/MeOH (10/1 (v/v), 50 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo to give the crude product as a brown solid (0.446 g), which was used directly in the next step without further purification.MS (ESI, pos.ion) m/z: 312.4 [M+H]+.

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3F3N2

Synthesis of 3-methoxy-5-nitro-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)pyridine To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (30 mL) under an argon atmosphere were added potassium carbonate (6.70 g, 48.61 mmol) and 4-(trifluoromethyl)-1H-imidazole (1.7 g, 12.76 mmol) at room temperature. The reaction mixture was stirred at 50 C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-5-nitro-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)pyridine (1.4 g, 46%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.65 (s, 1H), 8.45 (s, 1H), 8.44 (s, 1H), 4.11 (s, 3H); LCMS: 288.8 (M+1); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 mum); RT 3.46 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/CH2Cl2 (Rf: 0.4).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 17325-26-7

1H-Imidazole-4-carboxlic acid methyl ester (293.8mg, 2.33mmol), 4-bromo-6- cyclohexyl-pyrane-2-one (300mg, 1. 17mmol) and potassium carbonate (483. 8mg, 3. 50MMOL) were introduced into a 50ML flask, and the flask was then filled with nitrogen gas. After acetonitrile (LOML) was added thereto, the reaction solution was refluxed for 2 hours and then cooled down to room temperature. The precipitate was filtered off, and the filtrate was distilled under reduced pressure. The residue was purified by column chromatography on silica gel using MC: MEOH (20: 1) as eluent. The fractions containing the product were combined and evaporated to give a white solid (290mg, 82.2%). ‘H-NMR (CDCI3) ; 8 =7.99 (2H, m), 6.19 (2H, m), 3.98 (3H, s), 2.52 (1H, m), 1.99 (5H, M), 1.40 (5H, m).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C & C RESEARCH LABORATORIES; WO2004/50624; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: (1-Methyl-1H-imidazol-2-yl)methanol

Synthesis of 2-(Chloromethyl)-1-methyl-1H-imidazole Hydrochloride (BB7) To a solution of (BB6) (35.5 g, 316.96 mmol) in DCM (1500 mL) was added SOCl2 (330 mL, 4436 mmol) at 0 C. The reaction was warmed to ambient temperature and stirred for 5 h. The reaction mixture was concentrated, the residue was washed with DCM (2*500 mL), followed by Et2O (2*200 mL) to obtain (BB7) (50 g, 95%) as an off-white solid. Rf: 0.4 (EtOAc). 1H NMR (400 MHz, DMSO-d6): delta 7.76 (1H, app d), 7.70 (1H, app d), 5.17 (2H, s), 3.87 (3H, s); ink 131 (MH)+.

The synthetic route of (1-Methyl-1H-imidazol-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; ST GEORGE’S HOSPITAL MEDICAL SCHOOL; US2012/322722; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem