Reaction #619156

ord-700020d1ef35467e9cca23cb1469e3d7

Reaction equation

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
Cl.O=S1(=O)CCNCC1
1,1-dioxo-thiomorpholine hydrochloride
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
→
O=C(Nc1ncc(CN2CCS(=O)(=O)CC2)s1)N(C1CCCCC1)C1CCCCC1
desired product
Yield 18.0%
O=C(Nc1ncc(CN2CCS(=O)(=O)CC2)s1)N(C1CCCCC1)C1CCCCC1
1,1-Dicyclohexyl-3-[5-(1,1-dioxo-thiomorpholin-4-ylmethyl)-thiazol-2-yl]-urea
Yield 18.0%

Reactants

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
Cl.O=S1(=O)CCNCC1
1,1-dioxo-thiomorpholine 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 (67 mg, 0.20 mmol), 1,1-dioxo-thiomorpholine hydrochloride (52 mg, 0.30 mmol) and sodium triacetoxyborohydride (51 mg, 0.24 mmol) to afford 16 mg (18%) of the desired product after purification.

Source

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