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 → 5,8-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-ethyl}-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1054933Notes

Reaction equation

HRID 1054933 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH:11]=[CH:12][C:13]3[N:17]([CH2:18][C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:28])=[N:4][CH:3]=1>C(OCC)(=O)C.CO>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH2:18][C:19]([F:21])([F:20])[F:22])[N:16]=[C:15]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:28])=[N:4][CH:3]=1

Participants

3

Reactant 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]pyrazine

Product 1

HCID 727043245,8-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-ethyl}-[1,2,4]triazolo[1,5-a]pyrazineYield 54.7%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Was prepared in the same manner as described in General Procedure Example 2 using 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 (20 mg, 51.0 μmol, Eq: 1.00) as starting material. The crude material was applied on a 5 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 5,8-dimethyl-2-{2-[5-pyrrolidin-1-yl-2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-ethyl}-[1,2,4]triazolo[1,5-a]pyrazine (11 mg/52.4%) as a white solid. MS: m/e=395.8 (M+H+)

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-a5f18f55bb7e4e9e9d192457c672e3d2
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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