Reaction #619162

ord-2d0581b83d9e4152882e8b1c25c6cffa

Reaction equation

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
CCCS(=O)(=O)N1CCNCC1.Cl
1-propanesulfonyl-piperazine hydrochloride
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
→
CCCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CC1
desired product
Yield 27.4%
CCCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CC1
1,1-Dicyclohexyl-3-{5-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-thiazol-2-yl}-urea
Yield 27.4%

Reactants

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
CCCS(=O)(=O)N1CCNCC1.Cl
1-propanesulfonyl-piperazine hydrochloride
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPrepared

Procedure

Prepared as described in general procedure (P) using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (50 mg, 0.15 mmol), 1-propanesulfonyl-piperazine hydrochloride (52 mg, 0.23 mmol) and sodium triacetoxyborohydride (48 mg. 0.23 mmol) to afford 21 mg (27%) of the desired product after purification.

Source

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