Reacción #43864

ord-7718b043250649d284903c947caef11e

Ecuación de reacción

O=C(Cl)C1CCCCC1
Cyclohexanecarbonyl chloride
CCCc1nc2cc(NCc3ccccc3)ccc2n1CC(=O)OC(C)(C)C
(5-benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester
CCN(C(C)C)C(C)C
DIEA
CCCc1nc2cc(N(Cc3ccccc3)C(=O)C3CCCCC3)ccc2n1CC(=O)OC(C)(C)C
subtitle compound
CCCc1nc2cc(N(Cc3ccccc3)C(=O)C3CCCCC3)ccc2n1CC(=O)OC(C)(C)C
[5-(Benzyl-cyclohexanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónfiltered through an Extrelut column
  2. 2
    LavadoThe Extrelut column was washed with CH2Cl2
  3. 3
    Concentraciónthe filtrate was concentrated

Procedimiento

Cyclohexanecarbonyl chloride (48 μL, 0.36 mmol) was added to a solution of (5-benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester (45 mg, 0.12 mmol), DIEA (41 μL, 0.24 mmol) and DMAP (15 mg, 0.12 mmol) in CH2Cl2 (1 mL), and stirred overnight at room temperature. The reaction solution was diluted with aqueous HCl (1.0 M) and filtered through an Extrelut column. The Extrelut column was washed with CH2Cl2, and the filtrate was concentrated to afford the subtitle compound that was used without further purification. MS calculated for C30H39N3O3+H: 490, observed: 490.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732618B2uspto-grants-2010_06