5-Chloro-2-methyl-1,8-naphthyridine → N-{3-[4-Methyl-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-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]([CH3:12])=[N:7]2.[NH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[S:21][C:22]1[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=1>>[CH3:20][C:18]1[CH:17]=[CH:16][C:15]([S:21][C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=2)=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1Participants
3
Procedure
The product from Example 1d (100 mg, 0.559 mmol) was reacted with the product from Example 71c (152 mg, 0.559 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (45 mg, 18%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.97 (s, 3H), 2.38 (s, 3H), 2.74 (s, 3H), 6.26 (d, J=6.99 Hz, 1H), 6.84 (d, J=8.46 Hz, 1H), 7.06 (t, J=8.09 Hz, 1H), 7.25 (d, J=8.09 Hz, 1H), 7.33-7.41 (m, 2H), 7.41-7.54 (m, 2H), 7.74 (d, J=8.82 Hz, 1H), 8.33 (d, J=6.99 Hz, 1H), 8.89 (d, J=8.82 Hz, 1H), 9.81 (s, 1H), 10.91 (s, 1H); MS (ESI+) m/z 415 (M+H)+, (ESI−) m/z 413 (M−H)−.
Sources & evidence
- ORD record
- ord-58bceb56820f41dcbf7b7663e82c77f2
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763731B2
Reaction notes
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