(2R)-2-(Trifluoromethyl)pyrrolidine → 5,8-dimethyl-2-{(E)-2-[2-methyl-5-((R)-2-trifluoromethyl-pyrrolidin-1-yl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1055020Notes

Reaction equation

HRID 1055020 reaction equation
Br[C:2]1[N:6]=[C:5](/[CH:7]=[CH:8]/[C:9]2[N:17]=[C:16]3[N:11]([C:12]([CH3:19])=[N:13][CH:14]=[C:15]3[CH3:18])[N:10]=2)[N:4]([CH3:20])[N:3]=1.[F:21][C:22]([F:29])([F:28])[C@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1>>[CH3:19][C:12]1[N:11]2[N:10]=[C:9](/[CH:8]=[CH:7]/[C:5]3[N:4]([CH3:20])[N:3]=[C:2]([N:24]4[CH2:25][CH2:26][CH2:27][C@@H:23]4[C:22]([F:29])([F:28])[F:21])[N:6]=3)[N:17]=[C:16]2[C:15]([CH3:18])=[CH:14][N:13]=1

Participants

3

Reactant 2

HCID 7015082(2R)-2-(Trifluoromethyl)pyrrolidineHCID 90018333(E)-2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 900175585,8-dimethyl-2-{(E)-2-[2-methyl-5-((R)-2-trifluoromethyl-pyrrolidin-1-yl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-c]pyrimidineYield 14.5%

Procedure

Was prepared in the same manner as described in Example 87a) using (E)-2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine (100 mg, 299 μmol, Eq: 1.00) instead of 2-[(E)-2-(5-Bromo-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine and (R)-2-(trifluoromethyl)-pyrrolidine (83.3 mg, 598 μmol, Eq: 2) instead of pyrrolidin-2-one affording 5,8-dimethyl-2-{(E)-2-[2-methyl-5-((R)-2-trifluoromethyl-pyrrolidin-1-yl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-c]pyrimidine (17 mg, 14.5%) as a light yellow solid. MS: m/z=393.4 (M+H+)

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-9b79a0b745884f3ca9fd64ac921ac65b
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…