Reaction #619122

ord-5575f1b89a064cef8392e9264748b161

Reaction equation

CC(=O)Nc1ncc(S(=O)(=O)Cl)s1
2-acetylamino-thiazole-5-sulfonyl chloride
Br
HBr
CC(=O)O
acetic acid
CCOC(=O)N1CCC(N)CC1
ethyl 4-amino-1-piperidine carboxylate
C1CCC(NC2CCCCC2)CC1
dicyclohexylamine
→
CCOC(=O)N1CCC(NS(=O)(=O)c2sc(NC(=O)N(C3CCCCC3)C3CCCCC3)nc2C)CC1
4-[2-(3,3-Dicyclohexyl-ureido)-4-methyl-thiazole-5-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester
Cc1nc(NC(=O)N(C2CCCCC2)C2CCCCC2)sc1S(=O)(=O)NC1CCNCC1
title compound
Cc1nc(NC(=O)N(C2CCCCC2)C2CCCCC2)sc1S(=O)(=O)NC1CCNCC1
2-(3,3-Dicyclohexylureido)-4-methylthiazole-5-sulfonic acid piperidin-4-ylamide

Reactants

CC(=O)Nc1ncc(S(=O)(=O)Cl)s1
2-acetylamino-thiazole-5-sulfonyl chloride
Br
HBr
CC(=O)O
acetic acid
CCOC(=O)N1CCC(N)CC1
ethyl 4-amino-1-piperidine carboxylate
C1CCC(NC2CCCCC2)CC1
dicyclohexylamine

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

4-[2-(3,3-Dicyclohexyl-ureido)-4-methyl-thiazole-5-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester was prepared as described in Example 173 using ethyl 4-amino-1-piperidine carboxylate, dicyclohexylamine and 2-acetylamino-thiazole-5-sulfonyl chloride. Reaction with 33% HBr in acetic acid followed by chromatography afforded the title compound.

Source

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