4-Fluorobenzene-1,2-diamine → HCID 49805132, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26]([OH:28])=O)=[CH:21][CH:20]=[CH:19]2.[F:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([NH2:37])[CH:31]=1>>[NH2:37][C:32]1[CH:31]=[C:30]([F:29])[CH:35]=[CH:34][C:33]=1[NH:36][C:26]([C:22]1[C:23]2[C:18](=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1)=[O:28]Participants
3
Procedure
The title compound (39.1 mg, 81% yield) was prepared as a brown solid from 6-(6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid (37.5 mg, 0.1 mmol) and 4-fluoro-o-phenylenediamine (15.1 mg, 0.12 mmol) by an analogous procedure to that described in example 16. 1H NMR (DMSO-d6) δ 3.93 (s, 3H, —OCH3), 3.95 (s, 3H, —OCH3), 5.31 (s, 2H, benzene-NH2), 6.40 (s, 1H, Ar—H), 6.55-6.59 (m, 2H, Ar—H), 7.30 (d, J=7.6 Hz, 1H, Ar—H), 7.42 (s, 1H, Ar—H), 7.54-7.57 (m, 2H, Ar—H), 7.64 (t, J=8.0 Hz, 1H, Ar—H), 7.89-7.91 (m, 2H, Ar—H), 8.07 (d, J=8.0 Hz, 1H, Ar—H), 8.42 (d, J=9.2 Hz, 1H, Ar—H), 8.49 (d, J=5.2 Hz, 1H, Ar—H), 9.79 (s, 1H, benzene-NH). LC-MS (m/z) 484 (M+1).
Sources & evidence
- ORD record
- ord-f984a8b6cd7d4a488fa3467f7ab3129a
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211901B2
Reaction notes
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