(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009277, compound

HRID 1630231Notes

Reaction equation

HRID 1630231 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]1)(=[O:4])[CH3:3].[CH2:15]([C@H:22]1[CH2:26][NH:25][C@H:24]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:2]([N:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:25]2[CH2:26][C@H:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][C@H:24]2[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])=[O:14])[CH2:9][CH2:10]1)(=[O:4])[CH3:3]

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67010654HCID 67010654, compound

Product 1

HCID 67009277HCID 67009277, compoundYield 24.9%

Procedure

Proceeding as in Example 1, but substituting 2-(4-acetylpiperazin-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 115, (2S,4R)-1-(2-(4-acetylpiperazin-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (9.5 mg, 24.9%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.96 (s, 1H), 7.96 (s, 1H), 7.53-7.60 (m, 2H), 7.25-7.30 (m, 2H), 7.14-7.22 (m, 5H), 6.92-6.99 (m, 4H), 4.67-4.71 (m, 1H), 3.70-3.75 (m, 1H), 3.45-3.50 (m, 1H), 3.23-3.30 (m, 2H), 3.10-3.27 (m, 4H), 2.53-2.62 (m, 3H), 2.37-2.45 (m, 2H), 2.14-2.30 (m, 2H), 1.85-1.99 (m, 2H). MS (EI) for C31H33FN4O4. found 545.6 (MH+).

Sources & evidence

ORD record
ord-3161c4ab374c47738d908105b2df5547
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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