5-Amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazole → 1-(3-tert-butyl-1-(6-methylpyridin-3-yl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-(3-oxo-3,4-dihydropyrido[3,2-b]pyrazin-8-yloxy)phenyl)urea

HRID 217878Notes

Reaction equation

HRID 217878 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]3[N:15]=[CH:16][C:17](=[O:19])[NH:18][C:13]=3[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:20][C:21](=[O:29])OC1C=CC=CC=1.[C:30]([C:34]1[CH:38]=[C:37]([NH2:39])[N:36]([C:40]2[CH:41]=[N:42][C:43]([CH3:46])=[CH:44][CH:45]=2)[N:35]=1)([CH3:33])([CH3:32])[CH3:31]>>[C:30]([C:34]1[CH:38]=[C:37]([NH:39][C:21]([NH:20][C:3]2[CH:4]=[CH:5][C:6]([O:8][C:9]3[C:14]4[N:15]=[CH:16][C:17](=[O:19])[NH:18][C:13]=4[N:12]=[CH:11][CH:10]=3)=[CH:7][C:2]=2[F:1])=[O:29])[N:36]([C:40]2[CH:41]=[N:42][C:43]([CH3:46])=[CH:44][CH:45]=2)[N:35]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

3

Reactant 2

HCID 114019745-Amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazoleHCID 59588837Phenyl 2-fluoro-4-(3-oxo-3,4-dihydropyrido[3,2-b]pyrazin-8-yloxy)phenylcarbamate

Product 1

HCID 595888601-(3-tert-butyl-1-(6-methylpyridin-3-yl)-1H-pyrazol-5-yl)-3-(2-fluoro-4-(3-oxo-3,4-dihydropyrido[3,2-b]pyrazin-8-yloxy)phenyl)ureaYield 17%

Procedure

Method F4 was used with 65 mg (0.17 mmol) of phenyl 2-fluoro-4-(3-oxo-3,4-dihydropyrido[3,2-b]pyrazin-8-yloxy)phenylcarbamate and 45 mg (0.2 mmol) of 3-tert-butyl-1-(6-methylpyridin-3-yl)-1H-pyrazol-5-amine (Regan, J. et al., J. Med. Chem. 2002, 45, 2994-3008). Obtained 15 mg, 17% yield of the title compound.

Sources & evidence

ORD record
ord-e972cf2e8b6d41fea49370d0ca5a017f
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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