(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009498, compound

HRID 1630214Notes

Reaction equation

HRID 1630214 reaction equation
Cl.[CH3:2][N:3]([CH3:11])[C:4](=[O:10])[CH2:5][CH2:6][C:7](O)=[O:8].[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:7](=[O:8])[CH2:6][CH2:5][C:4]([N:3]([CH3:11])[CH3:2])=[O:10])[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 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659484HCID 86659484, compound

Product 1

HCID 67009498HCID 67009498, compoundYield 20%

Procedure

Proceeding as in Example 1, but substituting 4-(dimethylamino)-4-oxobutanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 89, (2S,4R)-4-benzyl-1-(4-(dimethylamino)-4-oxobutanoyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (6.2 mg, 20%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.68 (s, 1H), 7.57 (m, 2H), 7.27 (m, 2H), 7.23-7.15 (m, 7H), 6.93 (m, 2H), 4.43 (m, 1H), 3.68 (m, 1H), 3.27 (m, 1H), 2.94 (s, 3H), 2.78 (s, 3H), 2.67-2.58 (m, 4H), 2.44 (m, 3H), 1.91 (m, 2H). MS (EI) for C30H32FN3O4. found 518.6 (MH+).

Sources & evidence

ORD record
ord-5401eb21698349a09892b491a7ddf8bc
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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