5-Fluoro-2-(pyrimidin-2-yl)benzoic acid → 2-(4,6-Dimethoxypyrimidin-2-yl)-5-[(5-fluoro-2-pyrimidin-2-ylphenyl)carbonyl]octahydropyrrolo[3,4-c]pyrrole

HRID 243941

Reaction equation

HRID 243941 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]2[CH2:18][CH:17]3[CH:13]([CH2:14][NH:15][CH2:16]3)[CH2:12]2)[N:4]=1.[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[C:24]([CH:28]=1)[C:25](O)=[O:26]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]2[CH2:18][CH:17]3[CH:13]([CH2:14][N:15]([C:25]([C:24]4[CH:28]=[C:20]([F:19])[CH:21]=[CH:22][C:23]=4[C:29]4[N:30]=[CH:31][CH:32]=[CH:33][N:34]=4)=[O:26])[CH2:16]3)[CH2:12]2)[N:4]=1

Participants

3

Reactant 2

HCID 670869505-Fluoro-2-(pyrimidin-2-yl)benzoic acidHCID 671164912-(4,6-Dimethoxy-pyrimidin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole

Product 1

HCID 529174642-(4,6-Dimethoxypyrimidin-2-yl)-5-[(5-fluoro-2-pyrimidin-2-ylphenyl)carbonyl]octahydropyrrolo[3,4-c]pyrrole

Procedure

The title compound was prepared in a manner analogous to Example 15 utilizing Intermediate 39 and Intermediate 13. MS (ESI) mass calcd. for C23H23FN6O3, 450.18; m/z found, 451.1 [M+H]+. 1H NMR (CDCl3): 8.68 (d, J=4.9 Hz, 2H), 8.25 (dd, J=8.7, 5.5 Hz, 1H), 7.28-7.15 (m, 2H), 7.12 (dd, J=8.6, 2.5 Hz, 1H), 5.31 (s, 1H), 3.84-3.65 (m, 7H), 3.63-3.33 (m, 5H), 3.13-2.86 (m, 4H).

Sources & evidence

ORD record
ord-9b62ec5d60884c75b85551d3493e9240
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Linked notes

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