8-(4-amino-3-(methylthio)phenoxy)pyrido[3,2-b]pyrazin-3(4H)-one → 1-(3-tert-butyl-1-(6-methoxypyridin-3-yl)-1H-pyrazol-5-yl)-3-(2-(methylthio)-4-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenyl)urea

HRID 217841Notes

Reaction equation

HRID 217841 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:12]3[N:13]=[CH:14][C:15](=[O:17])[NH:16][C:11]=3[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[S:20][CH3:21].[C:22]([C:26]1[CH:30]=[C:29]([N:31]=[C:32]=[O:33])[N:28]([C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[N:38][CH:39]=2)[N:27]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([C:26]1[CH:30]=[C:29]([NH:31][C:32]([NH:1][C:2]2[CH:19]=[CH:18][C:5]([O:6][C:7]3[C:12]4[N:13]=[CH:14][C:15](=[O:17])[NH:16][C:11]=4[N:10]=[CH:9][CH:8]=3)=[CH:4][C:3]=2[S:20][CH3:21])=[O:33])[N:28]([C:34]2[CH:39]=[N:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[N:27]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 469010918-(4-amino-3-(methylthio)phenoxy)pyrido[3,2-b]pyrazin-3(4H)-oneHCID 866478995-(3-tert-butyl-5-isocyanato-1H-pyrazol-1-yl)-2-methoxypyridine

Product 1

HCID 441330151-(3-tert-butyl-1-(6-methoxypyridin-3-yl)-1H-pyrazol-5-yl)-3-(2-(methylthio)-4-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenyl)ureaYield 53%

Procedure

Method F2 was used with 8-(4-amino-3-(methylthio)phenoxy)pyrido[3,2-b]pyrazin-3(4H)-one and 5-(3-tert-butyl-5-isocyanato-1H-pyrazol-1-yl)-2-methoxypyridine to afford the title compound (97 mg, 53%) as a white powder.

Sources & evidence

ORD record
ord-f0354a3d76144794a7a29954f476d9a2
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

Loading…