(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377582, compound

HRID 1630219Notes

Reaction equation

HRID 1630219 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([F:10])[C:4]=1[CH2:11][C:12]([OH:14])=O.[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>>[CH2:15]([C@H:22]1[CH2:26][N:25]([C:12](=[O:14])[CH2:11][C:4]2[C:5]([F:10])=[CH:6][CH:7]=[C:8]([F:9])[C:3]=2[F:2])[C@H:24]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=3)=[CH:32][CH:31]=2)=[O:28])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 670093532-(2,3,6-Trifluorophenyl)acetic acid hydrochloride

Product 1

HCID 45377582HCID 45377582, compoundYield 49.8%

Procedure

Proceeding as in Example 1, but substituting 2-(2,3,6-trifluorophenyl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 84, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(2,3,6-trifluorophenyl)acetyl)pyrrolidine-2-carboxamide (16.8 mg, 49.8%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): a 9.93 (s, 1H), 7.52 (d, 2H), 7.39 (m, 1H), 7.32-7.15 (m, 9H), 7.09 (m, 1H), 6.93 (m, 2H), 4.46 (m, 1H), 3.79 (m, 3H), 3.38 (m, 1H), 2.70 (m, 3H), 1.93 (m, 2H). MS (EI) for C32H26F4N2O3. found 563.6 (MH+).

Sources & evidence

ORD record
ord-a08307cc1dd3410180f4f9f1f45e3a05
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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