Reaction #341020

ord-188051a89acd4a57a34bca991b9fa4bd

Reaction equation

CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
O=C1CNCCN1
2-piperazinone
CC(=O)O
acetic acid
→
O=C1CN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CCN1
desired product
Yield 40.0%
O=C1CN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CCN1
1,1-Dicyclohexyl-3-[5-(3-oxo-piperazin-1-ylmethyl)-thiazol-2-yl]-urea
Yield 40.0%

Reactants

CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
O=C1CNCCN1
2-piperazinone
CC(=O)O
acetic acid

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 (40 mg, 0.12 mmol), 2-piperazinone (18 mg, 0.18 mmol), acetic acid (7 μL, 0.12 mmol) and sodium triacetoxyborohydride (38 mg, 0.18 mmol) to afford 20 mg (40%) of the desired product after purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07872139B2uspto-grants-2011_01