4-chloro-2,6-dimethylpyrimidine → 2-(2,6-Dimethylpyrimidin-4-yl)-5-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

HRID 1525017Notes

Reaction equation

HRID 1525017 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]([CH3:31])[N:25]=1>>[CH3:31][C:26]1[N:25]=[C:24]([N:14]2[CH2:15][CH:16]3[CH2:17][N:10]([C:8]([C:6]4[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[N:18]4[N:22]=[CH:21][CH:20]=[N:19]4)=[O:9])[CH2:11][CH:12]3[CH2:13]2)[CH:29]=[C:28]([CH3:30])[N:27]=1

Participants

3

Reactant 2

HCID 31541994-chloro-2,6-dimethylpyrimidineHCID 67116387(5-Fluoro-2-[1,2,3]triazol-2-yl-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone

Product 1

HCID 671162262-(2,6-Dimethylpyrimidin-4-yl)-5-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

Procedure

The title compound was prepared in a manner analogous to Example 15 utilizing Intermediate 21 and 4-chloro-2,6-dimethyl-pyrimidine. MS (ESI): mass calculated for C21H22FN7O, 407.45, m/z found 408.2 [M+H]+. 1H NMR (CDCl3) 7.97 (dd, J=9.0, 4.8 Hz, 1H), 7.73 (s, 2H), 7.25-7.19 (m, 1H), 7.16-7.10 (m, 1H), 5.94 (s, 1H), 3.95-2.88 (m, 10H), 2.50 (s, 3H), 2.34 (s, 3H).

Sources & evidence

ORD record
ord-af9a08b987034c50a24ff76de6cb9888
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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