Acetic Anhydride → 3'-Acetylamino4'-benzoyl-6-methyl-biphenyl-3-carboxylic acid cyclopropylamide
Reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:16]([NH2:28])[CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:16]([NH:28][C:36](=[O:38])[CH3:37])[CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[CH2:2][CH2:3]1Participants
6
Procedure
To a solution of the 3′-Amino-4′-benzoyl-6-methyl-biphenyl-3-carboxylic acid cyclopropylamide from Example 14 (21 mg, 0.057 mmol) and triethyl amine (29 mg, 0.284 mmol) in 1.5 mL methylene chloride was added acetic anhydride (8.7 mg, 0.085 mmol) at room temperature. The reaction mixture was stirred at that temperature for 6 hours. The mixture was diluted with 50 mL of ethyl acetate and was washed with sat. aqueous NaHCO3 (10 mL), water (10 mL), and brine (10 mL), dried over MgSO4, and the solvents were evaporated. The residue was purified by preparative TLC sheet (ethyl acetate:hexanes=1:1) to give a colorless solid (20 mg, 85%).
Workup
- washwas washed with sat. aqueous NaHCO3 (10 mL), water (10 mL), and brine (10 mL)
- dry with materialdried over MgSO4
- customthe solvents were evaporated
- customThe residue was purified by preparative TLC sheet (ethyl acetate:hexanes=1:1)
Sources & evidence
- ORD record
- ord-079bd96303784adc8327957327ced053
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700622B2
Reaction notes
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