(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377719, compound

HRID 1630234Notes

Reaction equation

HRID 1630234 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([OH:15])=O)[CH2:8][CH2:7]1.[CH2:16]([C@H:23]1[CH2:27][NH:26][C@H:25]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[CH:33][CH:32]=2)=[O:29])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([C@H:23]1[CH2:27][N:26]([C:13](=[O:15])[CH2:12][N:9]2[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][O:3][CH3:2])[CH2:11][CH2:10]2)[C@H:25]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)=[CH:33][CH:32]=2)=[O:29])[CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009820HCID 67009820, compound

Product 1

HCID 45377719HCID 45377719, compoundYield 26.3%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(2-methoxyethyl)piperazin-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 100, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(4-(2-methoxyethyl)piperazin-1-yl)acetyl)pyrrolidine-2-carboxamide (10.6 mg, 26.3%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.96 (s, 1H), 7.61 (d, 1H), 7.54 (d, 1H), 7.28 (m, 2H), 7.22-7.13 (m, 5H), 6.99-6.92 (m, 4H), 4.45 (m, 1H), 3.73 (m, 1H), 3.39 (m, 2H), 3.23 (t, 1H), 3.20 (s, 2H), 3.13 (s, 2H), 3.07 (m, 1H), 2.63 (m, 2H), 2.48 (m, 8H), 2.43 (t, 2H), 2.09 (t, 1H), 1.91 (m, 2H). MS (EI) for C33H39FN4O4. found 575.7 (MH+).

Sources & evidence

ORD record
ord-8db321997a9f4269a21f733d0b8a7beb
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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