Reaction #619159

ord-4571c48832ed4eaaa0f9cb27f7bb3252

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
CC(C)(C)OC(=O)N1CCNCC1
piperazine-1-carboxylic acid tert-butyl ester
CC(=O)O
acetic acid
→
CC(C)(C)OC(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CC1
desired product
Yield 55.0%
CC(C)(C)OC(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CC1
4-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester
Yield 55.0%

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
CC(C)(C)OC(=O)N1CCNCC1
piperazine-1-carboxylic acid tert-butyl ester
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 (1.0 g, 3.0 Mmol), piperazine-1-carboxylic acid tert-butyl ester (838 mg, 4.5 mmol), acetic acid (40 μL, 0.6 mmol) and sodium triacetoxyborohydride (765 mg, 3.6 mmol) to afford 835 mg (55%) of the desired product after purification.

Source

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