Oxalyl chloride → 3-Chloro-6-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)picolinamide
Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[C:16]2[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1.[Cl:23][C:24]1[C:25]([C:38](O)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][CH:29]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:25]([C:38]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[N:10]=[CH:9][CH:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:28][CH:29]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The title compound was prepared following the procedure described in Example-1 using 4-(3-(trifluoromethyl)phenoxy)quinolin-8-amine (Intermediate-11, 100 mg, 0.327 mmol), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 180 mg, 0.66 mmol), oxalyl chloride (125 mg, 0.99 mmol), DMF (1 drop) and DIPEA (126 mg, 0.98 mmol) in CH2Cl2 (5 mL) to afford 70 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 11.86 (s, 1H), 8.91 (d, J=6.9 Hz, 1H), 8.81 (d, 1H), 8.35 (br t, 1H), 8.12 (d, J=7.8 Hz, 1H), 8.06 (d, J=9.1 Hz, 1H), 7.80-7.70 (m, 5H), 7.47 (d, J=7.8 Hz, 1H), 6.83 (d, J=4.8 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 1.16 (s, 9H); MS [M+H]+: 557.26.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-e8dc5cb8e4f540219d4e84a5587e6aed
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006257B2
Reaction notes
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