Reaction #619123

ord-bced78e4dfd5416785c08db43257826d

Reaction equation

O[C@H](CS)[C@@H](O)CS
dithioerythritol
CI
methyl iodide
CC(C)(C)OC(=O)N1CCC(N(C(=O)Nc2ncc(SC#N)s2)C2CCCCC2)CC1
4-[1-cyclohexyl-3-(5-thiocyanato-thiazol-2-yl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester
→
CSc1cnc(NC(=O)N(C2CCCCC2)C2CCN(C(=O)c3cccs3)CC2)s1
title compound
CSc1cnc(NC(=O)N(C2CCCCC2)C2CCN(C(=O)c3cccs3)CC2)s1
1-Cyclohexyl-3-(5-methylsulfanyl-thiazol-2-yl)-1-[1-(thiophene-2-carbonyl)-piperidin-4-yl]-urea
CSc1cnc(NC(=O)N(C2CCCCC2)C2CCN(C(=O)OC(C)(C)C)CC2)s1
4-[1-Cyclohexyl-3-(5-methylsulfanyl-thiazol-2-yl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester

Reactants

O[C@H](CS)[C@@H](O)CS
dithioerythritol
—
( I )
CI
methyl iodide
CC(C)(C)OC(=O)N1CCC(N(C(=O)Nc2ncc(SC#N)s2)C2CCCCC2)CC1
4-[1-cyclohexyl-3-(5-thiocyanato-thiazol-2-yl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherRemoval of the Boc group and N-acylation

Procedure

4-[1-Cyclohexyl-3-(5-methylsulfanyl-thiazol-2-yl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester was prepared as described in general procedure (H) and (I) using 4-[1-cyclohexyl-3-(5-thiocyanato-thiazol-2-yl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester, dithioerythritol and methyl iodide. Removal of the Boc group and N-acylation using thiophene-2 carboxylic acid as described in general procedure (G), steps 3 and 4 gave the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045183E1uspto-grants-2014_10