Reacción #619083

ord-dcf5ebbe7d3e40ecb5e3a5bbd7e135a5

Ecuación de reacción

C1CCC(NC2CCCCC2)CC1
Dicyclohexylamine
Nc1nccs1
aminothiazole
O=C(n1ccnc1)n1ccnc1
carbonyldiimidazole
O=C(Nc1nccs1)N(C1CCCCC1)C1CCCCC1
title product
O=C(Nc1nccs1)N(C1CCCCC1)C1CCCCC1
1,1-Dicyclohexyl-3-thiazol 2 yl urea

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGthe reaction stirred overnight at room temperature
  2. 2
    Lavadowashed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL)
  3. 3
    Secadodried over magnesium sulphate
  4. 4
    Concentraciónconcentrated in vacuo
  5. 5
    Otrothe residue purified by HPLC (Gilson 1, X-terra column; 0-100% CH3CN/H2O/0, 1% TFA; 15 min; flow 50 ml/min)

Procedimiento

To a solution of aminothiazole (50 mg, 0.5 mmol) in dichloromethane was added carbonyldiimidazole (81 mg, 0.5 mmol) and the solution stirred 2 h at room temperature. Dicyclohexylamine (1 eq) was then added and the reaction stirred overnight at room temperature. The reaction mixture is then diluted with ethyl acetate (8 mL), washed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL), dried over magnesium sulphate, concentrated in vacuo, and the residue purified by HPLC (Gilson 1, X-terra column; 0-100% CH3CN/H2O/0, 1% TFA; 15 min; flow 50 ml/min) to give the title product (52 mg).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE045183E1uspto-grants-2014_10