Formic Acid → HCID 86617976, compound

HRID 1991483Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH3:11][O:12][C:13](=[O:46])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH:25]([C:32](=[O:41])[NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[CH:35]=3)[CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:23]3[CH:42]=[CH:43][CH:44]=[CH:45][C:22]=3[N:21]=2)=[CH:16][CH:15]=1>ClCCl>[CH3:11][O:12][C:13](=[O:46])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[C:32](=[O:41])[NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([NH:40][CH:1]=[O:3])[CH:35]=3)[C:23]3[CH:42]=[CH:43][CH:44]=[CH:45][C:22]=3[N:21]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of acetic anhydride (162 mg, 1.58 mmol, 2.2 equiv.) and formic acid (73 mg, 1.58 mmol, 2.2 equiv.) was heated to 60° C. for 15 minutes. The reaction was cooled to room temperature and a solution of 4-{1-[(3-amino-phenylcarbamoyl)-cyclohexyl-methyl]-1H-benzoimidazol-2-yl}-benzoic acid methyl ester (35 mg, 0.72 mmol, 1.0 equiv.) in dichloromethane (2 mL) was added and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was washed with 1 N HCl (2 mL) and the organic layer dried over magnesium sulphate. The reaction mixture was concentrated in vacuo to afford 4-{1-[cyclohexyl-(3-formylamino-phenylcarbamoyl)-methyl]-1H-benzoimidazol-2-yl}-benzoic acid methyl ester, 23 mg (62% yield) as a yellow solid, MS (ES+): 511 (M+H).

Workup

temperatureThe reaction was cooled to room temperature
washThe reaction mixture was washed with 1 N HCl (2 mL)
dry with materialthe organic layer dried over magnesium sulphate
concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-9539794a350d486c8378cc44415e4b77
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645785B2

Reaction notes

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