4-Chloro-6,7-dimethoxyquinoline → 4-[3-Benzamido-4-fluoroanilino]-6,7-dimethoxyquinoline Hydrochloride

HRID 1357702Notes

Reaction equation

HRID 1357702 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:32])=[C:21]([NH:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=1>>[ClH:1].[C:24]([NH:23][C:21]1[CH:22]=[C:17]([CH:18]=[CH:19][C:20]=1[F:32])[NH:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1)(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 11148928N-(5-Amino-2-fluorophenyl)benzamide

Product 1

HCID 227322544-[3-Benzamido-4-fluoroanilino]-6,7-dimethoxyquinoline Hydrochloride

Procedure

Using an analogous procedure to that described in Example 26, 4-chloro-6,7-dimethoxyquinoline was reacted with N-(5-amino-2-fluorophenyl)benzamide to give the title compound; NMR: 3.98 (s, 3H), 4.0 (s, 3H), 6.73 (d, 1H), 7.34 (m, 1H), 7.43 (s, 1H), 7.46 (d, 1H), 7.55 (m, 4H), 7.82 (dd, 1H), 7.98 (d, 2H), 8.13 (s, 1H), 8.37 (d, 1H), 10.32 (broad s, 1H), 10.67 (broad s, 1H); Mass: M+H+ 418.

Sources & evidence

ORD record
ord-8adb400c0ad6420987b786c150e7c4a4
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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