Formamide → N-Cyclopropyl-4-methyl-3-(4-phenyl-quinazolin-7-yl)-benzamide

HRID 643690Notes

Reaction equation

[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:22]=[C:21]4[C:16]([C:17]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[N:18][C:19](=O)[NH:20]4)=[CH:15][CH:14]=3)[CH:7]=2)[CH2:3][CH2:2]1.C(N)=O>C(O)(=O)C>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:22]=[C:21]4[C:16]([C:17]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)=[N:18][CH:19]=[N:20]4)=[CH:15][CH:14]=3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 180 °C

Procedure

The mixture of 3′-Amino-4′-benzoyl-6-methyl-biphenyl-3-carboxylic acid cyclopropylamide from Example 15 (20 mg, 0.054 mmol) and formamide (2.9 mg, 0.065 mmol) in 0.7 mL acetic acid was stirred at 180° C. for 10 minutes in microwave. The solvents were removed under reduced pressure. The residue was dissolved in 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 (methylene chloride:methanol=10:1) to give a colorless solid (4.6 mg, 22%)

Workup

customThe solvents were removed under reduced pressure
dissolutionThe residue was dissolved in 50 mL of ethyl acetate
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 (methylene chloride:methanol=10:1)

Sources & evidence

ORD record: ord-f5d94ed575c8448ba698192360299f3d
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700622B2

Reaction notes

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