HCID 60208666, compound → HCID 67009276, compound

HRID 1630229Notes

Reaction equation

HRID 1630229 reaction equation
Cl.[C:2]1([CH2:8][C:9]([OH:11])=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([C@H:19]1[CH2:23][NH:22][C@H:21]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([C@H:19]1[CH2:23][N:22]([C:9](=[O:11])[CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:21]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 60208666HCID 60208666, compoundHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009276HCID 67009276, compoundYield 43.9%

Procedure

Proceeding as in Example 1, but substituting 2-phenylacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 31, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-phenylacetyl)pyrrolidine-2-carboxamide (13.4 mg, 43.9%). 1H-NMR (400 MHz, DMSO-D6): σ 9.97 (s, 1H), 7.54 (t, 2H), 7.19 (m, 12H), 6.97 (m, 4H), 3.74 (m, 1H), 3.65 (s, 2H), 3.27 (m, 2H), 2.62 (m, 4H). MS (EI) for C32H29FN2O3: 509.6 (MH+).

Sources & evidence

ORD record
ord-47fe9ef98015458b8c3db3756f1b629c
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…