4'-Mercaptoacetanilide → 3-[3-(4-Acetamidophenylthio)-5-fluorophenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine

HRID 37551

Reaction equation

[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)=[O:3].[F:12][C:13]1[CH:14]=[C:15]([C:20]2([O:30][CH3:31])[CH2:24][CH2:23][N:22]([CH2:25][C:26]([F:29])([F:28])[F:27])[CH2:21]2)[CH:16]=[C:17](F)[CH:18]=1>>[C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:17]2[CH:16]=[C:15]([C:20]3([O:30][CH3:31])[CH2:24][CH2:23][N:22]([CH2:25][C:26]([F:27])([F:28])[F:29])[CH2:21]3)[CH:14]=[C:13]([F:12])[CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:1]

Participants

Reactant 2

HCID 707774'-Mercaptoacetanilide

HCID 199358173-(3,5-Difluorophenyl)-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine

Product 1

HCID 199358463-[3-(4-Acetamidophenylthio)-5-fluorophenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidineYield 54%

Procedure

Using an analogous procedure to that described in Example 6, 4-mercaptoacetanilide was reacted with 3-(3,5-difluorophenyl)-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine to give 3-[3-(4-acetamidophenylthio)-5-fluorophenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine in 54% yield, m.p. 127°-129° C.

Sources & evidence

ORD record: ord-24f1aee3b6fd4676991b1100df3f8a97
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420298

Linked notes

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