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

HRID 243939Notes

Reaction equation

HRID 243939 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:3]=1[C:4]([OH:6])=O.[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([N:27]2[CH2:34][CH:33]3[CH:29]([CH2:30][NH:31][CH2:32]3)[CH2:28]2)[N:20]=1>>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([N:27]2[CH2:34][CH:33]3[CH:29]([CH2:30][N:31]([C:4]([C:3]4[C:7]([C:11]5[N:16]=[CH:15][CH:14]=[CH:13][N:12]=5)=[CH:8][CH:9]=[CH:10][C:2]=4[F:1])=[O:6])[CH2:32]3)[CH2:28]2)[N:20]=1

Participants

3

Reactant 2

HCID 670866032-Fluoro-6-(2-pyrimidinyl)benzoic acidHCID 671164912-(4,6-Dimethoxy-pyrimidin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole

Product 1

HCID 529173912-(4,6-Dimethoxypyrimidin-2-yl)-5-[(2-fluoro-6-pyrimidin-2-ylphenyl)carbonyl]octahydropyrrolo[3,4-c]pyrrole

Procedure

The title compound was prepared in a manner analogous to Example 15 utilizing Intermediate 14 and Intermediate 39. MS (ESI) mass calcd. for C23H23FN6O3, 450.47; m/z found, 451.1 [M+H]+. 1H NMR (CDCl3): rotamers observed, 8.75-8.65 (m, 2H), 8.12-8.01 (m, 1H), 7.45-7.38 (m, 1H), 7.20-7.12 (m, 1H), 7.05 (t, J=4.9 Hz, 1H), 5.32 (s, 1H), 3.96-3.41 (m, 12.4H), 3.32-2.27 (m, 0.7H), 3.22-3.15 (m, 0.5H), 3.06-2.86 (m, 2.4H).

Sources & evidence

ORD record
ord-818d997f24cb4437a09cf34147de7b78
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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