5-Chloro-2-methyl-1,8-naphthyridine → 4-[2-(7-Methyl-[1,8]naphthyridin-4-ylamino)-4-phenoxymethyl-phenylsulfanyl]-phenol
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]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:13][C:14]3[CH:19]=[C:18]([CH2:20][O:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:17]=[CH:16][C:15]=3[S:28][C:29]3[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1Participants
3
Procedure
The product from Example 1d (0.037 g, 0.205 mmol) was reacted with the product from Example 221d (0.066 g, 0.205 mmol) for 16.5 hours 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 salt (0.041 g, 34%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3H) 5.13 (s, 2H) 6.31 (d, J=6.99 Hz, 1H) 6.79 (d, J=8.46 Hz, 2H) 6.88-7.12 (m, 4H) 7.20-7.36 (m, 4H) 7.46-7.56 (m, 2H) 7.81 (d, J=8.82 Hz, 1H) 8.48 (d, J=6.99 Hz, 1H) 9.02 (d, J=8.46 Hz, 1H) 10.01 (s, 1H); MS (ESI+) m/z 466.3 (M+H)+; (ESI−) m/z 464.2 (M−H)−.
Sources & evidence
- ORD record
- ord-0ffb4c7d49644376b444e6d0ce5f9482
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338605B2
Reaction notes
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