Reaktion #340992

ord-17af0617063f4d82b0e3f2633a67df23

Reaktionsgleichung

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)OC(C)(C)C)CC2)s1
4-[1-Cyclohexyl-3-(5-methylsulfanyl-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

Edukte

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

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07872139B2uspto-grants-2011_01