Triethylamine → (E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-but-3-enenitrile

HRID 660754

Reaction equation

[CH3:1][CH:2]([CH:5]=[CH2:6])[C:3]#[N:4].[CH2:7]([O:14][C:15]1[CH:20]=[C:19](I)[CH:18]=[CH:17][C:16]=1[N:22]1[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:7]([O:14][C:15]1[CH:20]=[C:19](/[CH:6]=[CH:5]/[CH:2]([CH3:1])[C:3]#[N:4])[CH:18]=[CH:17][C:16]=1[N:22]1[CH2:23][C:24](=[O:29])[NH:25][S:26]1(=[O:28])=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-methyl-but-3-enenitrile (18 mg, 0.225 mmol), 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (50 mg, 0.113 mmol), Pd(OAc)2 (5 mg, 0.023 mmol) and triethylamine (11 mg, 0.107 mmol) in THF (3 mL) is placed in a microwave vial and heated at 110° C. for 10 min. The mixture is filtered and the filtrate concentrated. The residue is purified by reverse phase HPLC to give the title compound.

Workup

filtrationThe mixture is filtered
concentrationthe filtrate concentrated
customThe residue is purified by reverse phase HPLC

Sources & evidence

ORD record: ord-14f89c40c83145309f7346db4efbc780
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Linked notes

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