HCID 12196794, compound → HCID 67010197, compound

HRID 1630197Notes

Reaction equation

HRID 1630197 reaction equation
Cl.[O:2]=[C:3]([CH3:9])[CH2:4][CH2:5][C:6]([OH:8])=O.[CH2:10]([C@H:17]1[CH2:21][NH:20][C@H:19]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)=[O:23])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([C@H:17]1[CH2:21][N:20]([C:6](=[O:8])[CH2:5][CH2:4][C:3](=[O:2])[CH3:9])[C@H:19]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[O:23])[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 12196794HCID 12196794, compoundHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67010197HCID 67010197, compoundYield 7.5%

Procedure

Proceeding as in Example 1, but substituting 4-oxopentanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 123, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(4-oxopentanoyl)pyrrolidine-2-carboxamide (2.2 mg, 7.5%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.88 (s, 1H), 7.55-7.60 (m, 2H), 7.29-7.32 (m, 2H), 7.17-7.23 (m, 5H), 6.95-7.02 (m, 4H), 4.45 (m, 1H), 3.65 (m, 1H), 3.25 (m, 1H), 2.60-2.69 (m, 3H), 2.57-2.59 (m, 2H), 2.44-2.53 (m, 2H), 2.45 (s, 3H), 1.92 (m, 2H). MS (EI) for C29H29FN2O4. found 489.5 (MH+).

Sources & evidence

ORD record
ord-c67b019c0711474a8f17aeee57dcbb0e
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…