4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline → 3-(4-Fluoro-phenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid [4-(6,7-dimethoxy-quinolin-4-yloxy)-3-methyl-phenyl]-amide

HRID 573451Notes

Reaction equation

HRID 573451 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:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[CH3:23].[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[C:36](=[O:37])[C:35]([C:38](O)=[O:39])=[CH:34][N:33]([CH:41]([CH3:43])[CH3:42])[C:32]2=[O:44])=[CH:27][CH:26]=1>>[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:21]=[CH:20][C:19]([NH:22][C:38]([C:35]2[C:36](=[O:37])[N:31]([C:28]3[CH:27]=[CH:26][C:25]([F:24])=[CH:30][CH:29]=3)[C:32](=[O:44])[N:33]([CH:41]([CH3:43])[CH3:42])[CH:34]=2)=[O:39])=[CH:18][C:17]=1[CH3:23]

Participants

3

Reactant 2

HCID 218911624-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-anilineHCID 895813413-(4-Fluorophenyl)-2,4-dioxo-1-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Product 1

HCID 904527193-(4-Fluoro-phenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid [4-(6,7-dimethoxy-quinolin-4-yloxy)-3-methyl-phenyl]-amide

Procedure

This compound was synthesized using 4-(6,7-Dimethoxy-quinolin-4-yloxy)-3-methyl-phenylamine and 3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid using the procedure for example 1. mp=238-240° C.; LCMS m/z=585 (M+1); 1H NMR (DMSO-d6) δ: 10.92 (s, 1H), 8.65 (s, 1H), 8.44 (d, 1H, J=6 Hz), 7.73-7.67 (m, 2H), 7.55 (s, 1H), 7.45-7.41 (m, 2H), 7.39-7.34 (m, 3H), 7.17 (d, 1H, J=8 Hz), 6.31 (d, 1H, J=4.5 Hz), 4.78 (p, 1H, J=6 Hz), 3.95 (s, 6H), 2.09 (s, 3H), 1.43 (d, 6H, J=7 Hz).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-5dbd3125d1ef4268a6a4211b727ec9f9
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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