Triethylamine → HCID 68838003, compound

HRID 660670Notes

Reaction equation

HRID 660670 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][S:5](=[O:10])(=[O:9])[NH:4]1)=[CH2:2].[CH2:11]([O:18][C:19]1[CH:24]=[C:23](I)[CH:22]=[CH:21][C:20]=1[N:26]1[S:30](=[O:32])(=[O:31])[N:29](CC[Si](C)(C)C)[C:28](=[O:39])[CH2:27]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:11]([O:18][C:19]1[CH:24]=[C:23](/[CH:2]=[CH:1]/[CH:3]2[CH2:8][CH2:7][CH2:6][S:5](=[O:10])(=[O:9])[NH:4]2)[CH:22]=[CH:21][C:20]=1[N:26]1[S:30](=[O:32])(=[O:31])[NH:29][C:28](=[O:39])[CH2:27]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-oneHCID 68838119HCID 68838119, compound

Product 1

HCID 68838003HCID 68838003, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-vinyl-[1,2]thiazinane 1,1-dioxide (107 mg, 0.664 mmol) (J. Org. Chem. 69, 6377 (2004)), 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (250 mg, 0.563 mmol), Pd(OAc)2 (13 mg, 0.058 mmol) and triethylamine (0.768 mL, 5.51 mmol) in MeCN (4 mL) is heated at 120° C. for 1.5 h in a microwave apparatus. The reaction mixture is concentrated and the residue purified by preparative HPLC to afford the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-5b9ad3e4c6374049bc5e7c86c62a29ff
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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