(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009431, compound

HRID 1630209Notes

Reaction equation

HRID 1630209 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[S:8][CH2:9][C:10]([OH:12])=O.[CH2:13]([C@H:20]1[CH2:24][NH:23][C@H:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([C@H:20]1[CH2:24][N:23]([C:10](=[O:12])[CH2:9][S:8][C:3]2[N:2]=[CH:7][CH:6]=[CH:5][N:4]=2)[C@H:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67010181HCID 67010181, compound

Product 1

HCID 67009431HCID 67009431, compoundYield 33.5%

Procedure

Proceeding as in Example 1, but substituting 2-(pyrimidin-2-ylthio)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 94, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(pyrimidin-2-ylthio)acetyl)pyrrolidine-2-carboxamide (10.9 mg, 33.5%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): a 9.92 (s, 1H), 8.59 (d, 2H), 7.53 (m, 2H), 7.27 (m, 2H), 7.23-7.15 (m, 8H), 6.93 (m, 2H), 4.47 (m, 1H), 4.09 (m, 2H), 3.78 (m, 1H), 3.39 (m, 1H), 2.68 (m, 3H), 1.93 (m, 2H). MS (EI) for C30H27FN4O3S. found 543.6 (MH+).

Sources & evidence

ORD record
ord-63e19238245345069862f8a9d0aee49c
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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