Acrylonitrile → (4-Cyano-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}-7-t-butyl-dimethylsiloxy-4,5,6,7-tetrahydrobenzo[b]thiophene-2-yl)carbamic acid t-butyl ester

HRID 1351317Notes

Reaction equation

HRID 1351317 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[S:9][C:10]([C:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH2:28])=[CH:11][C:12]=1[S:13](=[O:26])(=[O:25])[N:14]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:15])([CH3:4])([CH3:3])[CH3:2].[C:38](#[N:41])[CH:39]=[CH2:40]>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[S:9][C:10]2[CH:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:28][CH2:40][CH:39]([C:38]#[N:41])[C:11]=2[C:12]=1[S:13](=[O:25])(=[O:26])[N:14]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)[CH3:15])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 69415031(5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester

Product 1

HCID 69416430(4-Cyano-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}-7-t-butyl-dimethylsiloxy-4,5,6,7-tetrahydrobenzo[b]thiophene-2-yl)carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of (5-[1-(t-butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]methyl-sulfamoyl}-thiophene-2-yl)carbamic acid t-butyl ester (the compound of Preparation Example 113) (235 mg) and acrylonitrile (4 lpL) in xylene (1 mL) was irradiated with a 200 W microwave. After reacting at 100° C. to 150° C. for 30 minutes, the reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate) and (4-cyano-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}-7-t-butyl-dimethylsiloxy-4,5,6,7-tetrahydrobenzo[b]thiophene-2-yl)carbamic acid t-butyl ester (54 mg) was obtained as a mixture. In addition, the same reaction was carried out from the starting materials (293 mg), and the mixture (45 mg) was obtained.

Workup

  1. customwas irradiated with a 200 W microwave
  2. customthe reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7fb2f24647bb4cdea7bfeb6e9478d170
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…