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

HRID 1630268Notes

Reaction equation

HRID 1630268 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=O)[CH:5]=[CH:4][N:3]=[N:2]1.[Cl:10][C:11]1[CH:39]=[CH:38][C:14]([CH2:15][C@H:16]2[CH2:20][NH:19][C@H:18]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)=[O:22])[CH2:17]2)=[CH:13][CH:12]=1>>[N:1]1([CH2:6][C:7]([N:19]2[CH2:20][C@H:16]([CH2:15][C:14]3[CH:38]=[CH:39][C:11]([Cl:10])=[CH:12][CH:13]=3)[CH2:17][C@H:18]2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)=[O:22])=[O:9])[CH:5]=[CH:4][N:3]=[N:2]1

Participants

3

Reactant 2

HCID 190184992-(1H-1,2,3-triazol-1-yl)acetic acidHCID 67010612(2S,4R)-4-(4-chlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 45376366(2S,4R)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-(4-chlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,3-triazol-1-yl)acetic acid and (2S,4R)-4-(4-chlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 228, (2S,4R)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-(4-chlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide. 1H-NMR (400 MHz, CDCl3): δ 8.94 (s, 1H), 7.79 (s, 1H), 7.56 (s, 1H), 7.43 (d, 2H), 7.30 (d, 2H), 7.14 (d, 2H), 7.00 (t, 2H), 6.94-6.89 (m, 4H), 5.28 (d, 1H), 5.14 (d, 1H), 4.78 (d, 1H), 3.68 (dd, 1H), 3.26 (t, 1H), 3.04-2.91 (m, 1H), 2.88 (dd, 1H), 2.71-2.59 (m, 2H), 1.73-1.65 (m, 1H). MS (EI) for C28H25ClFN5O3 found 534.2 (MH+).

Sources & evidence

ORD record
ord-c34a4cbdb1514e6d9e111755eb6cf86b
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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