Reaction #619176

ord-63b23f1ac3e6492987ab26419e83c88e

Reaction equation

CCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCNCC3)C3CCC(C)CC3)s2)CC1.Cl
3-[5-(4-ethanesulfonyl-piperazin-1-ylmethyl)-thiazol-2-yl]-1-(4-methyl-cyclohexyl)-1-piperidin-4-yl-urea hydrochloride
O=C(Cl)c1ccc(F)cc1
4-fluorobenzoyl chloride
→
CCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCC(C)CC3)C3CCN(C(=O)c4ccc(F)cc4)CC3)s2)CC1
desired product
Yield 86.1%
CCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCC(C)CC3)C3CCN(C(=O)c4ccc(F)cc4)CC3)s2)CC1
3-[5-(4-Ethanesulfonyl-piperazin-1-ylmethyl)-thiazol-2-yl]-1-[1-(4-fluoro-benzoyl)-piperidin-4-yl]-1-(4-methyl-cyclohexyl)-urea
Yield 86.1%

Reactants

CCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCNCC3)C3CCC(C)CC3)s2)CC1.Cl
3-[5-(4-ethanesulfonyl-piperazin-1-ylmethyl)-thiazol-2-yl]-1-(4-methyl-cyclohexyl)-1-piperidin-4-yl-urea hydrochloride
—
TEA
O=C(Cl)c1ccc(F)cc1
4-fluorobenzoyl chloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPrepared

Procedure

Prepared as described in general procedure (N) using 3-[5-(4-ethanesulfonyl-piperazin-1-ylmethyl)-thiazol-2-yl]-1-(4-methyl-cyclohexyl)-1-piperidin-4-yl-urea hydrochloride (46 mg, 0.075 mmol), TEA (26 μL, 0.19 mmol) and 4-fluorobenzoyl chloride (10 μL, 0.083 mmol) and to afford 41 mg (86%) of the desired product after purification.

Source

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