N-(6,7-dimethoxyquinolin-4-yl)-N-methyl-benzene-1,4-diamine → 1-Ethyl-3-(4-fluorophenyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid {4-[(6,7-dimethoxy-quinolin-4-yl)-methylamino]-phenyl}-amide

HRID 573435Notes

Reaction equation

HRID 573435 reaction equation
[CH2:1]([N:3]1[CH:8]=[C:7]([C:9]([OH:11])=O)[C:6](=[O:12])[N:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:4]1=[O:20])[CH3:2].[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28][CH:27]=[C:26]2[N:35]([CH3:43])[C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1>>[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28][CH:27]=[C:26]2[N:35]([CH3:43])[C:36]1[CH:41]=[CH:40][C:39]([NH:42][C:9]([C:7]2[C:6](=[O:12])[N:5]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:4](=[O:20])[N:3]([CH2:1][CH3:2])[CH:8]=2)=[O:11])=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 89580706N-(6,7-dimethoxyquinolin-4-yl)-N-methyl-benzene-1,4-diamineHCID 895826181-Ethyl-3-(4-fluorophenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Product 1

HCID 904527001-Ethyl-3-(4-fluorophenyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid {4-[(6,7-dimethoxy-quinolin-4-yl)-methylamino]-phenyl}-amide

Procedure

This compound was synthesized using 1-ethyl-3-(4-fluorophenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and N-(6,7-dimethoxyquinolin-4-yl)-N-methyl-benzene-1,4-diamine by the method described for example 134. mp=199-202° C.; LCMS m/z=570 (M+1); 1H NMR (CDCl3) δ: 10.62 (s, 1H), 8.64 (d, 1H, J=5.0 Hz), 8.60 (s, 1H), 7.50 (d, 2H, J=9.0 Hz), 7.38 (s, 1H), 7.31 (s, 1H), 7.00 (d, 1H, J=5.3 Hz), 6.90 (s, 1H), 6.86 (d, 2H J=8.9 Hz), 4.01 (s, 1H), 4.00 (s, 3H), 3.63 (s, 3H), 3.44 (s, 3H).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-c9d7db6d95254dbb96f5fa2782d71df1
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

Loading…