Triethylamine → Ethyl 3-{6-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676057Notes

Reaction equation

HRID 1676057 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:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)([O-:33])=[O:32]>ClCCl>[N+:31]([C:34]1[CH:35]=[CH:36][C:37]([C:38]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[CH:8][N:7]([CH:10]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=3[CH:23]=2)=[O:39])=[CH:41][CH:42]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

Product 1

HCID 58653684Ethyl 3-{6-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Reagents, catalysts & solvents 1

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 4-nitrobenzoyl chloride (264 mg, 1.43 mmol). The solution was stirred at room temperature for 72 hours, and was then evaporated in vacuo. The residue was 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 II) RT=5.42 min, MH+ 459].

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and methanol (97:3)

Sources & evidence

ORD record
ord-2cfc113445fe4ae5af4eaaff79ef3cbc
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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