2-Aminobenzimidazole → HCID 178517390, 화합물

HRID 717743노트

반응식

HRID 717743 반응식
C[O:2][C:3](=O)[C:4]([I:8])=[CH:5]OC.[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19].C[O-].[Na+]>C(O)C>[I:8][C:4]1[C:3](=[O:2])[N:19]=[C:11]2[NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]2[CH:5]=1

참가 물질

5

반응물 3

HCID 136242-AminobenzimidazoleHCID 10942334Sodium MethoxideHCID 54067316Methyl 2-iodo-3-methoxyprop-2-enoate

생성물 1

HCID 178517390HCID 178517390, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of 2-iodo-3-methoxy-acrylic acid methyl ester (1, 1.21 g, 5 mmol), 1H-benzoimidazol-2-ylamine (2, 0.67 g, 5 mmol) and ethanol (30 mL) was added a solution of sodium methoxide (10 mL, 0.5 M in methanol, 5 mmol). The resulted mixture was refluxed for 3 h and concentrated to afford 3-iodo-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-2-one (3). A mixture of (3-tert-butoxycarbonylamino-propyl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]carbamic acid tert-butyl ester (4, 490 mg, 1 mmol), 3 (311 mg, 1 mmol), K2CO2 (414 g, 3 mmol), Pd(PPh3)4 (0) (41 mg, 0.05 mmol), ethanol (6 mL), dioxane (2 mL) and water (2 mL) was degassed and heated at 80° C. for 20 h under argon atmosphere. The reaction mixture was diluted with EtOAc (500 mL), washed with water (300 mL) and brine (300 mL). The organic solution was concentrated and purified by flash chromatography (0%-6% MeOH in methanechloride) to give desired product 5 (170 mg, 31%) as light yellow solid. LCMS (EI) m/z: 570 (M+Na+).

후처리

  1. temperatureThe resulted mixture was refluxed for 3 h
  2. concentrationconcentrated

출처 및 근거

ORD 기록
ord-762fffeaaf6a40a9969978715fb6985b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193731B2

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