((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride → 5,8-dimethyl-2-(2-(3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1054932Notes

Reaction equation

HRID 1054932 reaction equation
[Cl-].[CH3:2][C:3]1[N:8]2[N:9]=[C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[C:7]2[C:6]([CH3:32])=[N:5][CH:4]=1.[N:33]1([C:38]2[N:42]=[C:41]([CH:43]=O)[N:40]([CH2:45][C:46]([F:49])([F:48])[F:47])[N:39]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH3:2][C:3]1[N:8]2[N:9]=[C:10]([CH:12]=[CH:43][C:41]3[N:40]([CH2:45][C:46]([F:49])([F:47])[F:48])[N:39]=[C:38]([N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[N:42]=3)[N:11]=[C:7]2[C:6]([CH3:32])=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 86665503((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chlorideHCID 900164053-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazole-5-carbaldehyde

Product 1

HCID 1233348515,8-dimethyl-2-(2-(3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyrazineYield 27.6%

Procedure

Was prepared in the same manner as described in General Procedure Example 1g) using ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (85 mg, 185 μmol, Eq: 1.00), 3-(pyrrolidin-1-yl)-1-(2,2,2-trifluoroethyl)-1H-1,2,4-triazole-5-carbaldehyde (50.6 mg, 204 μmol, Eq: 1.1) as starting materials. Chromatography afforded 5,8-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-a]pyrazine (20 mg/27.5%) as a white viscous oil. MS: m/e=393.5 (M+H+)

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-64238677c4d140f890006a61cdf93924
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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