Reacción #90743

ord-4b8d06eb916a48c3ba85c5492f81550c

Ecuación de reacción

COc1ccc(CNc2ncnc3c2c(-c2ccc(C(=O)Nc4cc(C(F)(F)F)ccn4)cc2)nn3[C@@H]2CCCc3c2cnn3S(=O)(=O)c2ccc(C)cc2)c(OC)c1
(R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide
→
Nc1ncnc2c1c(-c1ccc(C(=O)Nc3cc(C(F)(F)F)ccn3)cc1)nn2[C@@H]1CCCc2[nH]ncc21
title compound
Rendimiento 53.0%
Nc1ncnc2c1c(-c1ccc(C(=O)Nc3cc(C(F)(F)F)ccn3)cc1)nn2[C@@H]1CCCc2[nH]ncc21
(R)-4-(4-amino-1-(4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide
Rendimiento 53.0%

Reactantes

COc1ccc(CNc2ncnc3c2c(-c2ccc(C(=O)Nc4cc(C(F)(F)F)ccn4)cc2)nn3[C@@H]2CCCc3c2cnn3S(=O)(=O)c2ccc(C)cc2)c(OC)c1
(R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

Reactivos

Ninguno

Disolventes

O=C(O)C(F)(F)F
TFA

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroRemoved the solvent
  2. 2
    Otropurified by preparative HPLC

Procedimiento

A solution of (R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (90 mg, 0.109 mmol) in TFA (3 mL) was stirred for 3 h at 100° C. Removed the solvent and purified by preparative HPLC to give the title compound (30 mg, yield 52.8%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09446130B2uspto-grants-2016_09