Oxalyl chloride → 2-(Difluoromethyl)-5-(isobutyramidomethyl)-N-(4-((2,2,2-trifluoroethyl)amino)quinazolin-8-yl)nicotinamide
Reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1.[F:18][CH:19]([F:36])[C:20]1[N:28]=[CH:27][C:26]([CH2:29][NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])=[CH:25][C:21]=1[C:22](O)=[O:23].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[F:36][CH:19]([F:18])[C:20]1[N:28]=[CH:27][C:26]([CH2:29][NH:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])=[CH:25][C:21]=1[C:22]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][N:6]=[C:5]2[NH:4][CH2:3][C:2]([F:1])([F:16])[F:17])=[O:23]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The title compound was prepared following the procedure described in Example-1 using N4-(2,2,2-trifluoroethyl)quinazoline-4,8-diamine (Intermediate-65, 48 mg, 0.20 mmol), 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid (Intermediate-66, 107 mg, 0.40 mmol), oxalyl chloride (50 mg, 0.40 mmol), DMF (1 drop) and DIPEA (127 mg, 0.99 mmol) in CH2Cl2 (2 mL) to afford 5 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.40 (s, 1H), 8.95 (t, 1H), 8.71 (d, 1H), 8.61 (s, 1H), 8.48 (t, 1H), 8.07 (m, 2H), 7.65 (t, 1H), 7.41-7.05 (t, J=54.0 Hz, 1H), 4.42 (m, 4H), 2.50 (m, 1H), 1.05 (d, J=7.2 Hz, 6H); MS [M+H]+: 497.52.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-21dc574596db4747837973489770f13d
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006257B2
Reaction notes
Loading…