4-Fluorobenzene-1,2-diamine → HCID 49805502, compound

HRID 1510013Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20]([C:24](O)=[O:25])=[CH:19][CH:18]=[CH:17]4)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[C:30]([NH2:35])[CH:29]=1>>[NH2:35][C:30]1[CH:29]=[C:28]([F:27])[CH:33]=[CH:32][C:31]=1[NH:34][C:24]([C:20]1[C:21]2[C:16](=[CH:15][C:14]([O:13][C:7]3[C:6]4[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[CH:23][CH:22]=2)[CH:17]=[CH:18][CH:19]=1)=[O:25]

Participants

Reactant 2

HCID 1645844-Fluorobenzene-1,2-diamine

HCID 24822772HCID 24822772, compound

Product 1

HCID 49805502HCID 49805502, compoundYield 73%

Procedure

The title compound (33.1 mg, 73% yield) was prepared as a brown solid from 6-(7-methoxyquinolin-4-yloxy)-1-naphthoic acid (34.5 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 3.95 (s, 3H, —OCH3), 5.27 (s, 2H, benzene-NH2), 6.41 (td, J=2.5 and 8.4 Hz, 1H, Ar—H), 6.57-6.61 (m, 2H, Ar—H), 7.30-7.36 (m, 2H, Ar—H), 7.45 (d, J=2.2 Hz, 1H, Ar—H), 7.56 (dd, J=2.2 and 9.2 Hz, 1H, Ar—H), 7.65 (t, J=7.6 Hz, 1H, Ar—H), 7.87-7.91 (m, 2H, Ar—H), 8.07 (d, J=8.3 Hz, 1H, Ar—H), 8.24 (d, J=9.1 Hz, 1H, Ar—H), 8.43 (d, J=9.2 Hz, 1H, Ar—H), 8.65 (d, J=5.1 Hz, 1H, Ar—H), 9.75 (s, 1H, benzene-NH). LC-MS (m/z) 454 (M+1).

Sources & evidence

ORD record: ord-36f6be6e7073433081b7fc1fa1276ccd
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211901B2

Reaction notes

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