3-Fluoro-2-(pyrimidin-2-yl)benzoic acid → (3-Fluoro-2-(pyrimidin-2-yl)phenyl)(5-(4,5,6-trimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone

HRID 244012Notes

Reaction equation

HRID 244012 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[CH2:11]2)[N:3]=1.[F:18][C:19]1[C:20]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](O)=[O:23]>>[F:18][C:19]1[C:20]([C:28]2[N:29]=[CH:30][CH:31]=[CH:32][N:33]=2)=[C:21]([C:22]([N:14]2[CH2:13][CH:12]3[CH:16]([CH2:17][N:10]([C:4]4[N:5]=[C:6]([CH3:9])[C:7]([CH3:8])=[C:2]([CH3:1])[N:3]=4)[CH2:11]3)[CH2:15]2)=[O:23])[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 670867703-Fluoro-2-(pyrimidin-2-yl)benzoic acidHCID 699393982-(4,5,6-Trimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrrole

Product 1

HCID 67116496(3-Fluoro-2-(pyrimidin-2-yl)phenyl)(5-(4,5,6-trimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone

Procedure

The title compound was prepared in a manner analogous to Example 15, utilizing Intermediate 42 and 3-fluoro-2-(pyrimidin-2-yl)benzoic acid. MS (ESI): mass calculated for C24H25FN6O, 432.21; m/z found 433.3 [M+H]+. 1H NMR (600 MHz, CDCl3): 8.41 (dd, J=4.7, 1.8, 2H), 7.66-7.54 (m, 2H), 7.34 (dd, J=7.4, 4.8, 2H), 3.94 (dd, J=12.1, 7.6, 2H), 3.80 (dd, J=11.5, 7.3, 1H), 3.74-3.46 (m, 4H), 3.31-3.01 (m, 3H), 2.40-2.13 (m, 9H).

Sources & evidence

ORD record
ord-7cca7e3db0504de88f95001bb4b74d53
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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