5-Chloro-2-propyl-[1,8]naphthyridine → N-{4-[2-(7-Propyl-[1,8]naphthyridin-4-ylamino)-4-trifluoromethyl-phenylsulfanyl]-phenyl}-acetamide
Reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.[NH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[S:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:29][CH:28]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:15][C:16]3[CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=[CH:18][C:17]=3[S:26][C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:29][CH:28]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH2:13][CH3:14]Participants
3
Procedure
The product from Example 2g (50 mg, 0.242 mmol) was reacted with the product from Example 35a (79.0 mg, 0.242 mmol) for 16 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the ditrifluoroacetic acid salt (10.5 mg, 10%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3H), 1.81-1.92 (m, J=7.35 Hz, 2H), 2.07 (s, 3H), 3.01 (t, J=7.54 Hz, 2H), 6.44 (d, J=6.99 Hz, 1H), 7.11 (d, J=8.46 Hz, 1H), 7.42-7.49 (m, J=8.46 Hz, 2H), 7.69 (d, J=8.82 Hz, 2H), 7.78 (dd, J=8.82, 1.47 Hz, 1H), 7.87 (d, J=8.82 Hz, 1H), 7.91 (d, J=1.10 Hz, 1H), 8.52 (d, J=6.99 Hz, 1H), 9.03 (d, J=8.46 Hz, 1H), 11.14 (s, 1H); MS (ESI+) m/z 497 (M+H)+, ESI− m/z 495 (M−H)−.
Sources & evidence
- ORD record
- ord-8a036c02e96645caa30e47a3008d78b1
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763731B2
Reaction notes
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