Reaction #341013

ord-2552d936c99940a7bdb56783ec4aed35

Reaction equation

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
CC(C)N
isopropylamine
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
→
CC(C)NCc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
desired product
Yield 42.0%
CC(C)NCc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-Dicyclohexyl-3-[5-(isopropylamino-methyl)-thiazol-2-yl]-urea
Yield 42.0%

Reactants

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
CC(C)N
isopropylamine
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 (100 mg. 0.30 mmol), isopropylamine (30 μL, 0.36 mmol) and sodium triacetoxyborohydride (101 mg, 0.48 mmol) to afford 47 mg (42%) of the desired product after purification.

Source

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