Triethylamine → (E)-3-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-N-isopropylacrylamide

HRID 660602Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([NH:33][C:34](=[O:37])[CH:35]=[CH2:36])([CH3:32])[CH3:31].C(N(CC)CC)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:36]=[CH:35]/[C:34]([NH:33][CH:30]([CH3:32])[CH3:31])=[O:37])[CH:12]=[CH:11][C:10]=1[N:16]1[CH2:17][C:18](=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:20]1(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (240 mg, 0.44 mmol), N-isopropylacrylamide (60 mg, 0.53 mmol) and triethylamine (445 mg, 0.44 mmol) in MeCN (5 mL) in a pressure vessel is added Pd(OAc)2 (5 mg) and the mixture is heated at 100° C. for 8 h. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (86:15) as eluent to give the title compound as a solid.

Workup

customThe solvent is removed under reduced pressure
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-019e86d1095c48ceabf95f65a0e683e3
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

Loading…