Reaction #341016

ord-680072fca91b484c9f8bafb79f601db5

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(=O)O
acetic acid
COC(=O)c1ccc(CN)cc1
4-aminomethyl-benzoic acid methyl ester
→
COC(=O)c1ccc(CNCc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)cc1
desired product
Yield 36.4%
COC(=O)c1ccc(CNCc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)cc1
4-({[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-methyl)-benzoic acid methyl ester
Yield 36.4%

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(=O)O
acetic acid
COC(=O)c1ccc(CN)cc1
4-aminomethyl-benzoic acid methyl ester

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 (150 mg. 0.42 mmol), acetic acid (24 μL, 0.42 mmol), 4-aminomethyl-benzoic acid methyl ester (170 mg, 0.84 mmol) and sodium triacetoxyborohydride (268 mg, 1.27 mmol) to afford 74 mg (36%) of the desired product after purification.

Source

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