Triethylamine → Ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676062ノート

反応式

HRID 1676062 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[CH:23]=1.C(N(CC)CC)C.[N+:31]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](Cl)=[O:38])([O-:33])=[O:32]>ClCCl.CN(C1C=CN=CC=1)C>[N+:31]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[CH:23]=1)=[O:38])([O-:33])=[O:32]

参加物

6

反応物 3

HCID 8471Triethylamine2 回HCID 8495Benzoyl chloride, 3-nitro-3 回HCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

生成物 1

HCID 58653702Ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a solution of ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate (200 mg, 647 μmol) in dichloromethane (15 mL) was added triethylamine (190 μL, 1.43 mmol) and 3-nitrobenzoyl chloride (264 mg, 1.43 mmol). The solution was stirred at room temperature for 96 hours, and DMAP (7.0 mg, 57 μmol) and 3-nitrobenzoyl chloride (120 mg, 647 μmol) was added, and the stirring continued at room temperature for 72 hours. Triethylamine (90 μL, 639 μmol), 3-nitrobenzoyl chloride (120 mg, 647 μmol) and DMAP (7.0 mg, 57 μmol) were then added. The solution was stirred at room temperature for 72 hours, evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (97:3), to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=5.52 min, MH+ 459].

後処理

  1. waitthe stirring continued at room temperature for 72 hours
  2. stirringThe solution was stirred at room temperature for 72 hours
  3. customevaporated in vacuo
  4. customthe residue purified by flash column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (97:3)

出典と根拠

ORDレコード
ord-b30d8b961563455996530915b4db67a2
出典データセット
uspto-grants-2011_08
特許番号
US08003806B2

反応ノート

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