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

HRID 1676062Notes

Reaction equation

HRID 1676062 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

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].

Workup

  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)

Sources & evidence

ORD record
ord-b30d8b961563455996530915b4db67a2
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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