3-Fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid → (5-(6,7-Difluoroquinoxalin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(3-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

HRID 244017Notes

Reaction equation

HRID 244017 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([N:13]1[CH2:20][CH:19]3[CH:15]([CH2:16][NH:17][CH2:18]3)[CH2:14]1)[CH:6]=[N:5]2.[F:21][C:22]1[C:23]([N:31]2[N:35]=[CH:34][CH:33]=[N:32]2)=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](O)=[O:26]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([N:13]1[CH2:14][CH:15]3[CH2:16][N:17]([C:25]([C:24]4[CH:28]=[CH:29][CH:30]=[C:22]([F:21])[C:23]=4[N:31]4[N:35]=[CH:34][CH:33]=[N:32]4)=[O:26])[CH2:18][CH:19]3[CH2:20]1)[CH:6]=[N:5]2

Participants

3

Reactant 2

HCID 670865493-Fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 699386886,7-Difluoro-2-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)quinoxaline

Product 1

HCID 67116418(5-(6,7-Difluoroquinoxalin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(3-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

Procedure

The title compound was prepared in a manner analogous to Example 15, utilizing Intermediate 44 and 3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid. MS (ESI): mass calculated for C23H18F3N7O, 465.15; m/z found 466.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.28 (s, 1H), 7.75 (d, J=20.8, 2H), 7.65 (dd, J=10.6, 8.4, 1H), 7.50 (tt, J=9.6, 4.8, 1H), 7.43 (dd, J=11.4, 8.0, 1H), 7.39-7.31 (m, 1H), 7.25 (dd, J=12.5, 4.9, 1H), 4.00-3.86 (m, 1H), 3.81 (dd, J=10.0, 5.6, 2H), 3.66-3.49 (m, 4H), 3.32-3.16 (m, 3H).

Sources & evidence

ORD record
ord-23ee138697294cb28ba47b17273c0f9c
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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