4-Chloro-1,8-naphthyridine → 4-[4-(4-Fluoro-benzyloxy)-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:14]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:17]2[CH:16]=[CH:15][C:14]([S:28][C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)=[C:13]([NH:12][C:2]3[C:11]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[N:5]=[CH:4][CH:3]=3)[CH:18]=2)=[CH:22][CH:23]=1Participants
3
Procedure
The product from Example 16c (50 mg, 0.30 mmol) was reacted with the product from 4-[2-amino-4-(4-fluoro-benzyloxy)-phenylsulfanyl]-phenol (102 mg, 0.30 mmol) for 20 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 (99 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 5.11 (s, 2H) 6.31 (d, J=6.99 Hz, 1H) 6.64 (d, J=8.45 Hz, 2H) 7.08-7.27 (m, 6H) 7.50 (m, J=5.51 Hz, 2H) 7.91 (d, J=4.41 Hz, 1H) 8.47 (d, J=6.98 Hz, 1H) 9.13 (dd, J=1.47 Hz, J=8.45 Hz, 1H) 9.17 (dd, J=1.47 Hz, J=4.05 Hz, 1H) 9.79 (s, 1H) 11.14 (br s, 1H) 14.50 (br s, 1H); MS (ESI+) m/z, 470 (M+H−TFA)+; (ESI−) m/z, 468 (M−H−TFA)−.
Sources & evidence
- ORD record
- ord-574b5c70c24e48f6b72a30a150b2c67e
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338605B2
Reaction notes
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