2-(2H-1,2,3-triazol-2-yl)acetic acid → (2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide

HRID 1630272Notes

Reaction equation

HRID 1630272 reaction equation
[N:1]1[N:2]([CH2:6][C:7]([OH:9])=O)[N:3]=[CH:4][CH:5]=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:3]1[N:2]([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])[N:1]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 234341642-(2H-1,2,3-triazol-2-yl)acetic acidHCID 67009205(2S,4R)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide

Product 1

HCID 46191539(2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide

Procedure

Proceeding as in Example 1, but substituting 2-(2H-1,2,3-triazol-2-yl)acetic acid and (2S,4R)—N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide, gave Compound 169, (2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(2,4,6-trifluorobenzyl)pyrrolidine-2-carboxamide. Major isomer: 1H-NMR (400 MHz, CDCl3): δ 9.12 (s, 1H), 7.72 (s, 2H), 7.43-7.38 (m, 2H), 7.03-6.86 (m, 6H), 6.72-6.64 (m, 2H), 5.12 (s, 2H), 4.82 (d, 1H), 3.63-3.57 (m, 1H), 3.22 (t, 1H), 2.92-2.74 (m, 3H), 2.59 (dd, 1H), 1.78-1.69 (m, 1H). MS (EI) for C28H23F4N5O3 found 554 (MH+).

Sources & evidence

ORD record
ord-089abf9034884d5c8d347be3da4b3da0
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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