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

HRID 1630269Notes

Reaction equation

HRID 1630269 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:39]=[CH:38][CH:37]=[CH:36][C:12]=1[CH2:13][C@H:14]1[CH2:18][NH:17][C@H:16]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[O:20])[CH2:15]1>>[N:1]1([CH2:6][C:7]([N:17]2[CH2:18][C@H:14]([CH2:13][C:12]3[CH:36]=[CH:37][CH:38]=[CH:39][C:11]=3[F:10])[CH2:15][C@H:16]2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)=[CH:24][CH:23]=2)=[O:20])=[O:9])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 18101801,2,4-Triazole-1-acetic acidHCID 67009716(2S,4R)-4-(2-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009603(2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(2-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid and (2S,4R)-4-(2-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 106, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(2-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide. Major isomer: 1H-NMR (400 MHz, CDCl3): δ 9.00 (s, 1H), 8.24 (s, 1H), 7.98 (s, 1H), 7.42-7.38 (m, 2H), 7.27-7.18 (m, 3H), 7.13-6.86 (m, 7H), 5.06 (d, 1H), 4.98 (d, 1H), 4.78 (d, 1H), 3.72-3.66 (m, 1H), 3.31 (t, 1H), 3.004-2.92 (m, 1H), 2.90-2.77 (m, 2H), 2.60 (dd, 1H), 1.81-1.72 (m, 1H), 1.45-1.38 (m, 1H). MS (EI) for C28H25F2N5O3 found 518 (MH+).

Sources & evidence

ORD record
ord-aca3059b34044b0c9b35b54a6679d5b1
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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