N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-acrylamide → HCID 178493273, compound

HRID 630386Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([NH:18][C:19](=[O:22])[CH:20]=[CH2:21])=[C:12]([Cl:23])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:24][C:25]([C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)([C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)[C:26]([O:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH:35][CH3:36])[CH2:31][CH2:30]1)=[O:27]>C(Cl)Cl>[OH:24][C:25]([C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)([C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)[C:26]([O:28][C@H:29]1[CH2:30][CH2:31][C@H:32]([N:35]([CH2:21][CH2:20][C:19]([NH:18][C:13]2[CH:14]=[C:15]([O:16][CH3:17])[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:11][C:12]=2[Cl:23])=[O:22])[CH3:36])[CH2:33][CH2:34]1)=[O:27]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-acrylamide (intermediate 40; 0.9 g, 0.002 mol) and trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5; 0.7 g, 0.002 mol) in methylene chloride (20 mL) was stirred at 75° C. in a closed vessel for 64 hours. The solvent was evaporated and the crude obtained was purified by column chromatography with silica gel, eluting with chloroform/methanol (from 50/1 to 25/1) to give the title compound as a white-yellow solid (49%).

Workup

customThe solvent was evaporated
customthe crude obtained
customwas purified by column chromatography with silica gel
washeluting with chloroform/methanol (from 50/1 to 25/1)

Sources & evidence

ORD record: ord-fb23a10b75c84c1896e13a76cba18296
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315463B2

Reaction notes

Loading…