(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010497, compound

HRID 1630235Notes

Reaction equation

HRID 1630235 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH2:12][NH:13][CH2:14][C:15]([OH:17])=O.[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][NH:13][CH2:12][C:4]2[N:3]([CH3:2])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[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 67010834HCID 67010834, compound

Product 1

HCID 67010497HCID 67010497, compoundYield 30.4%

Procedure

Proceeding as in Example 1, but substituting 2-((1-methyl-1H-indol-2-yl)methylamino)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 30, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-((1-methyl-1H-indol-2-yl)methylamino)acetyl)pyrrolidine-2-carboxamide (12.6 mg, 30.4%). 1H-NMR (400 MHz, DMSO-D6): σ 9.95 (s, 1H), 7.93 (m, 2H), 7.26 (m, 4H), 7.17 (m, 8H), 6.96 (m, 3H), 4.15 (m, 1H), 3.64 (m, 1H), 3.49 (m, 2H), 3.14 (m, 2H), 2.87 (s, 3H), 2.64 (m, 2H), 2.20 (m, 1H), 1.89 (m, 2H). MS (EI) for C35H34FN5O3: 592.7 (MH+).

Sources & evidence

ORD record
ord-5c7b63e9b31344e8aad47dbb15e54916
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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