(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010236, compound

HRID 1630208Notes

Reaction equation

HRID 1630208 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:4]=1[CH2:10][C:11]([OH:13])=O.[CH2:14]([C@H:21]1[CH2:25][NH:24][C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([C@H:21]1[CH2:25][N:24]([C:11](=[O:13])[CH2:10][C:4]2[C:5]([F:9])=[CH:6][CH:7]=[CH:8][C:3]=2[F:2])[C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009300HCID 67009300, compound

Product 1

HCID 67010236HCID 67010236, compoundYield 37.6%

Procedure

Proceeding as in Example 1, but substituting 2-(2,6-difluorophenyl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 95, (2S,4R)-4-benzyl-1-(2-(2,6-difluorophenyl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (12.3 mg, 37.6%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): a 9.92 (s, 1H), 7.53 (m, 3H), 7.28 (m, 3H), 7.24-7.14 (m, 6H), 6.97-6.91 (m, 4H), 4.46 (m, 1H), 3.82 (m, 1H), 3.70 (m, 2H), 3.37 (m, 1H), 2.70 (m, 3H), 1.19 (m, 2H). MS (EI) for C32H27F3N2O3. found 545.6 (MH+).

Sources & evidence

ORD record
ord-54bac10a44e24b79a37b092d611414bd
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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