(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377718, compound

HRID 1630207Notes

Reaction equation

HRID 1630207 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[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:5]2[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=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 67010787HCID 67010787, compound

Product 1

HCID 45377718HCID 45377718, compoundYield 12.3%

Procedure

Proceeding as in Example 1, but substituting 2-(pyridin-4-ylthio)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 96, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(pyridin-4-ylthio)acetyl)pyrrolidine-2-carboxamide (4 mg, 12.3%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.97 (s, 1H), 8.34 (d, 2H), 7.55 (m, 2H), 7.33-7.28 (m, 5H), 7.25-7.18 (m, 6H), 6.95 (m, 2H), 4.49 (m, 1H), 4.14 (m, 2H), 3.86 (m, 1H), 3.56 (m, 1H), 2.69 (m, 3H), 1.95 (m, 2H). MS (EI) for C31H28FN3O3S. found 542.6 (MH+).

Sources & evidence

ORD record
ord-567ddee0940340c890d2ae7cdd150c1f
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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