Reacción #833566

ord-15978c47957c464ea36131eb8a8342cc

Ecuación de reacción

O
water
CC#CCn1c(Cl)nc2c(=O)n(CC#N)n(Cc3ccc4ccccc4n3)c(=O)c21
1-(but-2-ynyl)-2-chloro-5-cyanomethyl-6-(quinolin-2-ylmethyl)-5,6-dihydro-1H-imidazo[4,5-d]pyridazine-4,7-dione
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(C)OC(=O)N[C@@H]1CCCNC1
(R)-3-tert-butoxycarbonylaminopiperidine
CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c(=O)n(CC#N)n(Cc3ccc4ccccc4n3)c(=O)c21
(R)-1-(but-2-ynyl)-2-(3-tert-butoxycarbonylamino-piperidin-1-yl)-5-cyanomethyl-6-(quinolin-2-ylmethyl)-5,6-dihydro-1H-imidazo[4,5-d]pyridazine-4,7-dione

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe mixture is extracted three times with ethyl acetate
  2. 2
    SecadoThe combined organic phases are dried over sodium sulphate
  3. 3
    Otrothe solvent is removed
  4. 4
    OtroThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1)

Procedimiento

A solution of 0.14 g 1-(but-2-ynyl)-2-chloro-5-cyanomethyl-6-(quinolin-2-ylmethyl)-5,6-dihydro-1H-imidazo[4,5-d]pyridazine-4,7-dione, 0.15 g potassium carbonate and 0.07 g (R)-3-tert-butoxycarbonylaminopiperidine in 2 ml dimethylsulphoxide is stirred for 5 h at 60° C. Then water is added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, and then the solvent is removed. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07393847B2uspto-grants-2008_07