4-(6,7-Dimethoxy-quinolin-4-yloxy)-3-trifluoromethyl-phenylamine → 2-Ethyl-4-(4-fluoro-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid [4-(6,7-dimethoxy-quinolin-4-yloxy)-3-trifluoromethyl-phenyl]-amide

HRID 573457Notes

Reaction equation

HRID 573457 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[C:23]([F:26])([F:25])[F:24].[CH2:27]([N:29]1[C:34](=[O:35])[N:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[C:32](=[O:43])[C:31]([C:44](O)=[O:45])=[N:30]1)[CH3:28]>>[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:44]([C:31]2[C:32](=[O:43])[N:33]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[C:34](=[O:35])[N:29]([CH2:27][CH3:28])[N:30]=2)=[O:45])=[CH:18][C:17]=1[C:23]([F:25])([F:26])[F:24]

Participants

3

Reactant 2

HCID 895815674-(6,7-Dimethoxy-quinolin-4-yloxy)-3-trifluoromethyl-phenylamineHCID 895815722-Ethyl-4-(4-fluoro-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

Product 1

HCID 904527242-Ethyl-4-(4-fluoro-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid [4-(6,7-dimethoxy-quinolin-4-yloxy)-3-trifluoromethyl-phenyl]-amide

Procedure

This compound was synthesized using 4-(6,7-dimethoxy-quinolin-4-yloxy)-3-trifluoromethyl-phenylamine and 2-ethyl-4-(4-fluoro-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid using the procedure for example 1. mp=148-50° C.; LCMS m/z=626 (M+1); 1H NMR (DMSO): 10.95 (s, 1H), 8.52 (d, 1H), 8.32 (s, 1H), 8.04 (m, 1H), 7.35-7.49 (m, 8H), 6.60 (m, 1H), 4.08 (q, 2H, J=7Hz), 3.97 (s, 3H), 3.89 (s, 3H), 1.35 (t, 3H, J=7Hz).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-602d979820464821b2419d68d3e96a72
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

Loading…