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

HRID 1630266Notes

Reaction equation

HRID 1630266 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=O)[CH:5]=[CH:4][N:3]=[N:2]1.[F:10][C:11]1[CH:12]=[C:13]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:14][C@H:15]1[CH2:19][NH:18][C@H:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16]1>>[N:1]1([CH2:6][C:7]([N:18]2[CH2:19][C@H:15]([CH2:14][C:13]3[CH:37]=[CH:38][C:39]([F:40])=[C:11]([F:10])[CH:12]=3)[CH2:16][C@H:17]2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)=[O:21])=[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 67009113(2S,4R)-4-(3,4-difluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 46191538(2S,4R)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-(3,4-difluorobenzyl)-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-(3,4-difluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 226, (2S,4R)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-(3,4-difluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide. Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.97 (s, 1H), 8.00 (s, 1H), 7.72 (s, 1H), 7.56 (d, 2H), 7.42-7.31 (m, 2H), 7.24-7.06 (m, 3H), 7.04-6.91 (m, 4H), 5.44 (q, 2H), 4.55-4.49 (m, 1H), 3.88-3.78 (m, 1H), 3.42-3.33 (m, 2H), 2.80-2.68 (m, 3H), 2.02-1.94 (m, 2H). MS (EI) for C28H24F3N5O3. found 536.2 (MH+).

Sources & evidence

ORD record
ord-1dc13e3793b34263a32d4bf793d2678d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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