1,2,4-Triazole-1-acetic acid → HCID 46191472, compound

HRID 1630265Notes

Reaction equation

HRID 1630265 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][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[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=4)[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[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=3)[CH2:29][C@H:25]2[C:23]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:39][CH:38]=3)=[CH:17][CH:18]=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 67009248HCID 67009248, compound

Product 1

HCID 46191472HCID 46191472, compound

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-(3-methylbenzyl)pyrrolidine-2-carboxamide, gave Compound 171, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(3-methylbenzyl)pyrrolidine-2-carboxamide. Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.00 (s, 1H), 8.43 (s, 1H), 7.95 (s, 1H), 7.55 (d, 2H), 7.23-7.15 (m, 3H), 7.08-6.91 (m, 8H), 5.23 (q, 2H), 4.53-4.48 (m, 1H), 3.83-3.76 (m, 1H), 2.73-2.61 (m, 4H), 2.29 (s, 3H), 2.00-1.89 (m, 2H). MS (EI) for C29H28FN5O3. found 514.2 (MH+).

Sources & evidence

ORD record
ord-ae4bec9120844752836e80cb13dbc474
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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