(E)-1-(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)pyrrolidin-2-one → 1-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-pyrrolidin-2-one

HRID 1055012Notes

Reaction equation

[CH3:1][C:2]1[N:7]2[N:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:25])=[N:4][CH:3]=1>[Pd].CO>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:25])=[N:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (E)-1-(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)pyrrolidin-2-one (24 mg, 70.9 μmol, Eq: 1.00) and palladium on carbon 10% (7.5 mg, 7.1 μmol, Eq: 0.1) in methanol (15 ml) was stirred for 5 hours at 25° C. under hydrogen atmosphere. Additional catalyst (0.1 eq) was added and hydrogenation continued for another 6 hours until HPLC shows complete conversion. The catalyst was filtered off, the filtrate was evaporated affording 1-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-pyrrolidin-2-one (24 mg, 99.4%) as a colorless oil. MS: m/z=341.6 (M+H+)

Workup

waithydrogenation continued for another 6 hours until HPLC
filtrationThe catalyst was filtered off
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-b14ae0a748634a27882ce413bdbd8bb9
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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