(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009338, compound

HRID 1630227Notes

Reaction equation

HRID 1630227 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][O:5][C:4]2[CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:10]=[CH:11][C:3]1=2.[CH2:18]([C@H:25]1[CH2:29][NH:28][C@H:27]([C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)=[CH:35][CH:34]=2)=[O:31])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([C@H:25]1[CH2:29][N:28]([C:15](=[O:17])[CH2:14][CH2:13][CH2:12][C:9]2[CH:10]=[CH:11][C:3]3[O:2][CH2:7][CH2:6][O:5][C:4]=3[CH:8]=2)[C@H:27]([C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]3[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=3)=[CH:35][CH:34]=2)=[O:31])[CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009378HCID 67009378, compound

Product 1

HCID 67009338HCID 67009338, compoundYield 23.5%

Procedure

Proceeding as in Example 1, but substituting 4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)butanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 33, (2S,4R)-4-benzyl-1-(4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)butanoyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (8.4 mg, 23.5%). 1H-NMR (400 MHz, DMSO-D6): σ 9.93 (s, 1H), 7.54 (d, 2H), 7.26 (t, 2H), 7.18 (m, 5H), 6.98 (m, 4H), 6.71 (d, 1H), 6.45 (m, 2H), 4.45 (m, 1H), 4.17 (m, 4H), 3.57 (m, 1H), 3.14 (m, 1H), 2.64 (m, 3H), 2.64 (t, 2H), 2.19 (m, 2H), 1.87 (m, 2H), 1.70 (m, 2H). MS (EI) for C36H35FN2O5: 595.7 (MH+).

Sources & evidence

ORD record
ord-0501639a6f794aa6b86ed39e39283128
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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