5-Chloro-2-methyl-1,8-naphthyridine → 4-[4-(3-Bromo-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-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]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>>[Br:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([S:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=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 (57 mg, 0.319 mmol) was reacted with 4-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol (128 mg, 0.319 mmol) for 28 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 (118 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.76 (3H) 5.15 (s, 2H) 6.25 (d, J=6.99 Hz, 1H) 6.65 (d, J=8.46 Hz, 2H) 7.06-7.68 (m, 8H) 7.80 (d, J=8.46 Hz, 1H) 8.39 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.45 Hz, 1H) 9.78 (s, 1H) 11.02 (br s, 1H) 14.39 (br s, 1H); MS (ESI+) m/z 544, 546 (M+H−TFA)+; (ESI−) m/z 542, 544 (M−H−TFA)−.
Sources & evidence
- ORD record
- ord-e54b7d8c36ba4e7a83347e150d3212aa
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763731B2
Reaction notes
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