Reacción #88896

ord-d5b8c544639640a1a3d8d0b2a2d1e656

Ecuación de reacción

Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-fluoroadenosine
CNC(=O)c1cn[nH]c1
N-methylpyrazol-4-carboxamide
→
CNC(=O)c1cnn(-c2nc(N)c3ncn([C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O)c3n2)c1
2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine

Reactantes

Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-fluoroadenosine
CNC(=O)c1cn[nH]c1
N-methylpyrazol-4-carboxamide

Reactivos

Ninguno

Disolventes

CC#N.CS(C)=O
acetonitrile dimethylsulfoxide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otropreparation of polymorph D by a relatively complicated procedure

Procedimiento

PCT application WO 2012/149196 describes preparation of polymorph D by a relatively complicated procedure. First, a “cross coupling” reaction of 2-fluoroadenosine with N-methylpyrazol-4-carboxamide in an acetonitrile/dimethylsulfoxide mixture provides crude 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, which is then purified by reverse-phase chromatography using a methanol/water mixture. After concentrating at 150° C. under reduced pressure, polymorph D is obtained as a white solid substance containing variable amounts of water.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09441006B2uspto-grants-2016_09