2-Aminobenzimidazole → HCID 178517390、化合物

HRID 717743ノート

反応式

HRID 717743 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 178517390HCID 178517390、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-762fffeaaf6a40a9969978715fb6985b
出典データセット
uspto-grants-2015_11
特許番号
US09193731B2

反応ノート

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