(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010222, compound

HRID 1630203Notes

Reaction equation

HRID 1630203 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([OH:10])=O.[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:22][N:21]([C:8](=[O:10])[CH2:7][C:3]2[S:2][CH:6]=[CH:5][CH:4]=2)[C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009511HCID 67009511, compound

Product 1

HCID 67010222HCID 67010222, compoundYield 39.8%

Procedure

Proceeding as in Example 1, but substituting 2-(thien-2-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 117, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(thien-2-yl)acetyl)pyrrolidine-2-carboxamide (12.3 mg, 39.8%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.34 (s, 1H), 7.55-7.60 (m, 2H), 7.37-7.39 (m, 2H), 7.28-7.32 (m, 2H), 7.17-7.23 (m, 5H), 6.94-7.03 (m, 6H), 4.48-4.51 (m, 1H), 3.90 (d, 2H), 3.75-3.80 (m 1H), 3.56 (m, 1H), 2.63-2.73 (m, 3H), 1.88-1.97 (m, 2H). MS (EI) for C30H27FN2O3S. found 515.6 (MH+).

Sources & evidence

ORD record
ord-e471f3d2d56b4d899f3052f1d7b14310
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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