1,2,4-Triazole-1-acetic acid → (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide

HRID 1630271Notes

Reaction equation

HRID 1630271 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=O)[CH:5]=[N:4][CH:3]=[N:2]1.[F:10][C:11]1[CH:41]=[CH:40][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C@@H:25]3[CH2:29][C@@H:28]([CH2:30][C:31]4[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=4[F:39])[CH2:27][NH:26]3)=[O:24])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>>[N:1]1([CH2:6][C:7]([N:26]2[CH2:27][C@H:28]([CH2:30][C:31]3[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=3[F:39])[CH2:29][C@H:25]2[C:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:41][CH:40]=3)=[CH:21][CH:20]=2)=[O:24])=[O:9])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 18101801,2,4-Triazole-1-acetic acidHCID 67009205(2S,4R)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide

Product 1

HCID 45377721(2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid and (2S,4R)—N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide, gave Compound 108, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide. Major isomer: 1H-NMR (400 MHz, CDCl3): δ 8.96 (s, 1H), 8.32 (s, 1H), 8.12 (s, 1H), 7.38 (d, 2H), 7.03-6.85 (m, 6H), 6.73-6.64 (m, 2H), 5.08 (d, 1H), 5.02 (d, 1H), 4.76 (d, 1H), 3.78-3.72 (m, 1H), 3.31 (t, 1H), 3.00-2.68 (m, 3H), 2.56 (dd, 1H), 1.82-1.72 (m, 1H). MS (EI) for C28H23F4N5O3 found 554 (MH+).

Sources & evidence

ORD record
ord-66c37c3499fc4987bd444e901d695dfa
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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