Methanol → 3-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

HRID 1676069Notes

Reaction equation

HRID 1676069 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]C)=[O:13])[C:6]=2[CH:23]=1.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)C(C)C)(C)C.[CH3:42][OH:43]>>[NH:30]([C:31]([NH: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][CH3:15])=[O:13])[C:6]=2[CH:23]=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH2:30][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=1[C:42]([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]([OH:14])=[O:13])[C:6]=2[CH:23]=1)=[O:43]

Participants

6

Reactant 4

HCID 887MethanolHCID 7672Phenyl isocyanate2×HCID 81531Diisopropylethylamine2×HCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

Product 2

HCID 116110403-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acidHCID 58653678Methyl 3-{6-[(anilinocarbonyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Procedure

To a solution of ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate (150 mg, 485 μmol) in methanol (6 mL) was added phenyl isocyanate (50 μL, 460 μmol) and N,N-diisopropylethylamine (80 μL, 459 μmol). The solution was stirred at room temperature for 48 hours, and additional aliquots of phenyl isocyanate (10 μL, 92 μmol) and N,N-diisopropylethylamine (16 μL, 92 μmol) were added. The solution was stirred at room temperature for an additional 24 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 (95:5) to afford the title compound, [LCMS (Method A, Mobile Phase II) RT 5.13 min, MH+ 415].

Workup

  1. stirringThe solution was stirred at room temperature for an additional 24 hours
  2. customwas then evaporated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and methanol (95:5)

Sources & evidence

ORD record
ord-287c8a4a9c1f4163bc25625809bfbeb2
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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