4-Chloro-1,8-naphthyridine → 4-[4-(3-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][CH:24]=[C:23]([F:27])[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:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][C:17]1[CH:16]=[CH:15][C:14]([S:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[C:13]([NH:12][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:18]=1Participants
3
Procedure
The product from Example 16c (50 mg, 0.30 mmol) was reacted with 4-[2-amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol (102 mg, 0.30 mmol) for 22 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 (75 mg, 43%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 5.16 (s, 2H) 6.31 (d, J=7.36 Hz, 1 H) 6.64 (d, J=8.82 Hz, 2 H) 7.09-7.28 (m, 6 H) 7.29 (2, 1H) 7.44 (m, J=6.61 Hz, 1 H) 7.93 (dd, J=4.41 Hz, 1 H) 8.47 (d, J=6.98 Hz, 1 H) 9.14 (dd, J=1.47 Hz, J=8.46 Hz, 1 H) 9.18 (dd, J=1.47 Hz, J=4.41 Hz, 1 H) 9.79 (s, 1 H) 11.16 (br s,1 H) 14.52 (br s,1 H); MS (ESI+) m/z, 470 (M+H−TFA)+; (ESI−) m/z, 468 (M−H−TFA)−.
Sources & evidence
- ORD record
- ord-00adf96c614249eb99c024d0b0f0c769
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763731B2
Reaction notes
Loading…