(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009842, compound

HRID 1630223Notes

Reaction equation

HRID 1630223 reaction equation
Cl.[CH3:2][C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13]([OH:15])=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.[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][C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]=2[CH3:2])[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 67009507HCID 67009507, compound

Product 1

HCID 67009842HCID 67009842, compoundYield 36.2%

Procedure

Proceeding as in Example 1, but substituting 2-(2-methyl-1H-indol-3-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 37, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(2-methyl-1H-indol-3-yl)acetyl)pyrrolidine-2-carboxamide (12.2 mg, 36.2%). 1H-NMR (400 MHz, DMSO-D6): σ 10.78 (s, 1H), 9.91 (s, 1H), 7.53 (m, 2H), 7.41 (d, 1H), 7.15 (m, 8H), 6.94 (m, 6H), 4.59 (m, 1H), 3.67 (m, 2H), 3.54 (m, 1H), 3.33 (m, 1H), 3.19 (t, 1H), 2.87 (s, 2H), 2.60 (m, 2H), 2.24 (s, 3H). MS (EI) for C35H32FN3O3: 562.8 (MH+).

Sources & evidence

ORD record
ord-ba0625621ff74d72917f6366d4eed5cc
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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