(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → (2S,4R)-1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

HRID 1630174Notes

Reaction equation

HRID 1630174 reaction equation
Cl.[N:2]1([CH2:11][C:12]([OH:14])=O)[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH2:15]([C@H:22]1[CH2:26][NH:25][C@H:24]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[N:2]1([CH2:11][C:12]([N:25]2[CH2:26][C@H:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][C@H:24]2[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])=[O:14])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 670092502-(1H-benzo[d][1,2,3]triazol-1-yl)acetic acid hydrochloride

Product 1

HCID 45376097(2S,4R)-1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideYield 12%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 176, (2S,4R)-1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (17 mg, 12%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.95 (s, 1H), 8.04 (d, 1H), 7.77-7.64 (m, 1H), 7.59-7.49 (m, 3H), 7.44-7.12 (m, 8H), 7.07-6.90 (m, 4H), 5.80 (q, 2H), 4.56-4.48 (m, 1H), 4.02-3.93 (m, 1H), 3.55-3.46 (m, 1H), 2.85-2.69 (m, 3H), 2.08-1.94 (m, 2H). MS (EI) for C32H28FN5O3. found 549.9 (MH+).

Sources & evidence

ORD record
ord-aa013254e1884ceda7b1396a511cef06
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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