4-Chloro-6-methyl-2-(trifluoromethyl)pyrimidine → 2-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-5-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]octahydropyrrolo[3,4-c]pyrrole

HRID 243956Notes

Reaction equation

HRID 243956 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[C:6]([C:8]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[CH2:11]2)=[O:9])[CH:7]=1.Cl[C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([C:31]([F:34])([F:33])[F:32])[N:25]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[C:6]([C:8]([N:10]2[CH2:11][CH:12]3[CH:16]([CH2:15][N:14]([C:24]4[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([C:31]([F:33])([F:34])[F:32])[N:25]=4)[CH2:13]3)[CH2:17]2)=[O:9])[CH:7]=1

Participants

3

Reactant 2

HCID 250672674-Chloro-6-methyl-2-(trifluoromethyl)pyrimidineHCID 67116387(5-Fluoro-2-[1,2,3]triazol-2-yl-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone

Product 1

HCID 671163402-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-5-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]octahydropyrrolo[3,4-c]pyrrole

Procedure

The title compound was prepared in a manner analogous to Example 15 utilizing Intermediate 21 and 4-chloro-6-methyl-2-trifluoromethyl-pyrimidine. MS (ESI): mass calculated for C21H19F4N7O, 461.42; m/z found 462.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.04-7.87 (m, 1H), 7.81-7.63 (m, 1H), 7.29-7.18 (m, 1H), 7.17-7.08 (m, 1H), 6.31-6.03 (m, 1H), 4.13-2.84 (m, 10H), 2.44 (s, 3H).

Sources & evidence

ORD record
ord-f8d98abe3e2a44f6a58fe1321a5221c9
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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