4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 4-[2-(7-Isobutyl-[1,8]naphthyridin-4-ylamino)-4-methyl-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]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:7]2.[NH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[S:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:16][C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=3[S:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH:13]([CH3:15])[CH3:14]Participants
3
Procedure
The product from Example 12d (100 mg, 45.3 mmol) was reacted with the product from Example 4c (105 mg, 45.3 mmol) for 18 h following the procedure from Example 1g giving the title compound after purification of the crude product by HPLC with TFA as the trifluoroacetic acid salt (90 mg, 47%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.97 (d, J=6.62 Hz, 6H), 2.13-2.30 (m, 1H), 2.33 (s, 3H), 2.89 (d, J=6.99 Hz, 2H), 6.29 (d, J=6.99 Hz, 1H), 6.73 (d, J=8.46 Hz, 2H), 7.00 (d, J=8.09 Hz, 1H), 7.13-7.34 (m, 4H), 7.81 (d, J=8.46 Hz, 1H), 8.43 (d, J=6.99 Hz, 1H), 9.03 (d, J=8.46 Hz, 1H), 10.99 (br. s., 1H), 14.36 (br. s., 1H); MS (ESI+) m/z 416 (M+H)+; (ESI−) m/z 414 (M−H)−.
Sources & evidence
- ORD record
- ord-1945983d834546fa9338a58a8a4584f6
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763731B2
Reaction notes
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