Reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[NH:10][CH:9]([C:11]([OH:13])=O)[CH2:8][CH2:7]1.[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[C:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1)[N:21]([CH3:35])[C:20]2=[O:36].C(N(CC)CC)C>C1COCC1.CN(C=O)C>[CH3:35][N:21]1[C:20](=[O:36])[C:19]2[C:24](=[C:15]([NH:14][C:11]([CH:9]3[CH2:8][CH2:7][C:6](=[O:5])[NH:10]3)=[O:13])[CH:16]=[CH:17][CH:18]=2)[N:23]=[C:22]1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[CH:26]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Thionylchloride (83 mg, 0.7 mmol) was added to a solution of 5-oxopyrrolidine-2-carboxylic acid 19 (65 mg, 0.5 mmol) in THF (5 mL) at 0° C. DMF (1 drop) was added and the solution was allowed to warm to room temperature for 3 h then cooled to 0° C. A solution of 8-amino-3-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one 5 (65 mg, 0.2 mmol) and triethylamine (145 mg, 1.44 mmol) in THF (1 mL) was added and the reaction mixture was allowed to warm to room temperature and stirred for 12 h. The reaction mixture was concentrated to dryness and the crude residue was purified by preparative TLC to give Compound 339. MS (ESI) calcd for C21H17F3N4O3: 430.1. found: 431 [M+H].
Workup
- temperaturethen cooled to 0° C
- temperatureto warm to room temperature
- concentrationThe reaction mixture was concentrated to dryness
- customthe crude residue was purified by preparative TLC
Sources & evidence
- ORD record
- ord-39b8027fde4f46f28eacddcf04cf7944
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09326986B2
Linked notes
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