Cyclopropyl-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine → N-cyclopropyl-5-(2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)ethyl)-N,1-dimethyl-1H-1,2,4-triazol-3-amine

HRID 1054961Notes

Reaction equation

[CH:1]1([N:4]([CH3:24])[C:5]2[N:9]=[C:8]([CH:10]=[CH:11][C:12]3[N:22]=[C:15]4[C:16]([CH3:21])=[N:17][CH:18]=[C:19]([CH3:20])[N:14]4[N:13]=3)[N:7]([CH3:23])[N:6]=2)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([N:4]([CH3:24])[C:5]2[N:9]=[C:8]([CH2:10][CH2:11][C:12]3[N:22]=[C:15]4[C:16]([CH3:21])=[N:17][CH:18]=[C:19]([CH3:20])[N:14]4[N:13]=3)[N:7]([CH3:23])[N:6]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of N-cyclopropyl-5-(2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)vinyl)-N,1-dimethyl-1H-1,2,4-triazol-3-amine (23 mg, 70.9 μmol, Eq: 1.00) and palladium on carbon 10% (7.55 mg, 7.09 μmol, Eq: 0.1) in methanol (3.5 ml) was stirred for 14 hours at 25° C. under hydrogen atmosphere. Palladium was filtered off, the crude material was applied on silica gel and purified by column chromatography using ethy acetate/methanol (0-10% methanol) as eluent to give N-cyclopropyl-5-(2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)ethyl)-N,1-dimethyl-1H-1,2,4-triazol-3-amine (15 mg, 64.8%) as white waxy solid

Workup

filtrationPalladium was filtered off
custompurified by column chromatography

Sources & evidence

ORD record: ord-ad56db7c28b04a30a9425d436e69b6df
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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