Reaction #619166

ord-2910d3c50b284d85b54bac74f7d61588

Reaction equation

Cl.O=C(Nc1ncc(CN2CCNCC2)s1)N(C1CCCCC1)C1CCCCC1
1,1-dicyclohexyl-3-(5-piperazin-1-ylmethyl-thiazol-2-yl)-urea hydrochloride
CCN(C(C)C)C(C)C
DIEA
O=S(=O)(Cl)Cc1ccccc1
alpha-toluenesulfonyl chloride
→
O=C(Nc1ncc(CN2CCN(S(=O)(=O)Cc3ccccc3)CC2)s1)N(C1CCCCC1)C1CCCCC1
desired product
Yield 29.0%
O=C(Nc1ncc(CN2CCN(S(=O)(=O)Cc3ccccc3)CC2)s1)N(C1CCCCC1)C1CCCCC1
1,1-Dicyclohexyl-3-[5-(4-phenylmethanesulfonyl-piperazin-1-ylmethyl)-thiazol-2-yl]-urea
Yield 29.0%

Reactants

Cl.O=C(Nc1ncc(CN2CCNCC2)s1)N(C1CCCCC1)C1CCCCC1
1,1-dicyclohexyl-3-(5-piperazin-1-ylmethyl-thiazol-2-yl)-urea hydrochloride
CCN(C(C)C)C(C)C
DIEA
O=S(=O)(Cl)Cc1ccccc1
alpha-toluenesulfonyl chloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPrepared

Procedure

Prepared as described in general procedure (Q) using 1,1-dicyclohexyl-3-(5-piperazin-1-ylmethyl-thiazol-2-yl)-urea hydrochloride (26 mg, 0.05 mmol), DIEA (26 μL, 0.15 mmol) and alpha-toluenesulfonyl chloride (20 mg. 0.10 mmol) to afford 8 mg (29%) of the desired product after purification.

Source

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