Triethylamine → Ethyl 3-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

HRID 1676067Notes

Reaction equation

HRID 1676067 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][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37])([O-:33])=[O:32]>ClCCl>[N+:31]([C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([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:37])([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

Product 1

HCID 58653654Ethyl 3-{6-[(2-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 (200 μL, 1.43 μmol) and 2-nitrobenzoyl chloride (190 μL, 1.43 mmol). The solution was stirred at room temperature for 96 hours, and was 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=5.12 min, MH+ 459].

Workup

  1. customwas 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-a274750570f842fe9a4c1273d4700702
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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