* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 0.5h;
Example 35 -((3-carbamoyl-7-(2,4-dimethoxypyrimidin-5-yl)quinolin-4-yl)amino)-1-ethyl-1 H- benzordlimidazole-7-carboxylic acid ethyl 5-bromo-1 -ethyl-1 H-benzo[dlimidazole-7-carboxylate. To a mixture of 6- bromo-1 H-benzo[d]imidazole-4-carboxylic acid (200 mg, 0.830 mmol) in N,N- dimethylformamide (4 mL) were added cesium carbonate (1 190 mg, 3.65 mmol) and ethyl iodide (0.148 mL, 1 .825 mmol). The flask was equipped with a nitrogen balloon and the reaction mixture was heated to 50 C. After 30 minutes, LCMS indicated that no starting material remained and ~1 :1 mixture of regioisomers was present. The reaction mixture was allowed to cool to room temperature and diluted with water (40 mL; no precipitation observed) and ethyl acetate (50 mL). The ethyl acetate layer was dried over Na2S04, filtered and concentrated under reduced pressure. The crude residue was purified by reverse phase HPLC (ODS, 10-90% acetonitrile/water + 0.1 % trifluoroacetic acid). Appropriate fractions for the first peak to elute were combined, adjusted to pH ~7 and extracted with ethyl acetate twice. The combined extracts were dried over Na2S04, filtered and concentrated under reduced pressure to provide ethyl 6-bromo-1-ethyl-1 H- benzo[d]imidazole-4-carboxylate (89 mg, 0.300 mmol, 36.1 % yield) as a white solid. LCMS (ES+) m/e 297 [M+H]+. The work-up procedure described above was repeated with the second product to elute to provide ethyl 5-bromo-1 -ethyl- 1 H-benzo[d]imidazole-7-carboxylate (109 mg, 0.367 mmol, 44.2 % yield) as a pale yellow solid. LCMS (ES+) m/e 297 [M+H]+.
methyl 6-bromo-1-methyl-1H-benzo[d]imidazole-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83 mg
To a solution of <strong>[255064-08-5]6-bromo-1H-benzo[d]imidazole-4-carboxylic acid</strong>(200 mg,0.84mmol) in THF(5 mL) and MeOH(1 mL) at 0 C was added trimethylsilyldiazomethane inEt20(2.0 M,0.63 mL,1.3 mmol). The reaction was stirred for 1 hat 0 C then warmed toRT.The reaction was quenched by addition of AcOH dropwise and concentrated in vacuo. Thecrude residue was diluted with DCM(20 mL) and washed with brine(10 mL). The organiclayer was dried over MgS04,filtered,and concentrated in vacuo. To a solution of the cruderesidue in DMF(2 mL) was added NaH(30 mg,1.25 mmol) at RT and stirred for 30 min.methyl iodide(120 mg,0.84 mmol) was added,and the reaction was stirred for 4 h at RT.The reaction mixture was cooled to-78 C and quenched with MeOH. The mixture wasdiluted into DCM/H20(20 mL,1:1),the organic layer separated and the aqueous layer wasextracted with DCM(2 x 5 mL). The combined organic extracts were dried over MgS04,filtered,and concentrated in vacuo. The crude residue was purified by reverse phasepreparative HPLC(Phenomenex Gemini C 18,H20/CH3CN gradient to 20-80 % MeCN 0.1%TFA) to aHord the title compound(83 mg,37%).
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-bromobenzimidazole-4-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dimethyl sulfoxide; at 20℃;
To <strong>[255064-08-5]4-carboxy-6-bromobenzimidazole</strong> (3.49 g, 14.5 mmol), 3-aminomethyl-4,6-dimethylpyridin-2-one (3.32 g, 21.75 mmol,), EDCI (4.18g, 21.75mmol) and HOBT (2.94g, 21.75mmol) DMSO (15ml) N-methylmorpholine (5.87 g, 58 mmol) was quickly added to the solution. The solid slowly dissolved and allowed to react overnight at room temperature. The reaction solution was poured into ice water, stirred, allowed to stand, solid filtered, washed with water and dried to give a solid.
2,3-diamino-5-bromobenzoic acid ethyl ester[ No CAS ]
[ 255064-08-5 ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; In water;Reflux;
To 2,3-diamino-5-bromobenzoic acid ethyl ester (478 mg, 2 mmol) 4M diluted hydrochloric acid (6 ml) was added to a mixture with formic acid (6 mmol). The reaction was refluxed overnight. The reaction solution was spun to a solid.
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