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

HRID 1676070Notes

Reaction equation

HRID 1676070 reaction equation
[NH:1]([C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[CH:17][N:16]([CH:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][C:21]([O:23]C)=[O:22])[C:15]=2[CH:31]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](#[N:34])[CH3:33]>Cl>[NH:1]([C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[CH:17][N:16]([CH:19]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][C:21]([OH:23])=[O:22])[C:15]=2[CH:31]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:34][C:32]1[CH:4]=[CH:3][CH:2]=[CH:7][C:33]=1[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[CH:17][N:16]([CH:19]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][C:21]([OH:23])=[O:22])[C:15]=2[CH:31]=1)=[O:9]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 58653678Methyl 3-{6-[(anilinocarbonyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 2

HCID 116110403-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acidHCID 586536833-{6-[(Anilinocarbonyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 3-{6-[(anilinocarbonyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (90 mg, 210 μmol) in a mixture of hydrochloric acid (20 mL of a 5N solution) and acetonitrile (10 mL) was stirred at room temperature for 72 hours. The solution was evaporated in vacuo to afford the title compound, [LCMS (Method A, Mobile Phase II) RT=3.77 min, MH+ 401].

Workup

  1. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-2b5dcf0a029042fb8b091ba3a8e4c9f2
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

Loading…