Reacción #339040

ord-03749ae014754cee9f5c13ae3fb77111

Ecuación de reacción

COc1c(N2C[C@@H](C)N(C(=O)CCl)[C@@H](C)C2)c(F)cc2c(=O)c(C(=O)NCc3ccc(Cl)cc3Cl)cn(C3CC3)c12
compound
COc1c(N2C[C@@H](C)N(C(=O)CCl)[C@@H](C)C2)c(F)cc2c(=O)c(C(=O)NCc3ccc(Cl)cc3Cl)cn(C3CC3)c12
7-[(3R,5S)-4-(Chloroacetyl)-3,5-dimethylpiperazin-1-yl]-1-cyclopropyl-N-(2,4-dichlorobenzyl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide
[N-]=[N+]=[N-].[Na+]
sodium azide
→
COc1c(N2CC(C)N(C(=O)CN=[N+]=[N-])C(C)C2)c(F)cc2c(=O)c(C(=O)NCc3ccc(Cl)cc3Cl)cn(C3CC3)c12.Cl
7-[(3RS,5SR)-4-(Azidoacetyl)-3,5-dimethylpiperazin-1-yl]-1-cyclopropyl-N-(2,4-dichlorobenzyl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride

Reactantes

COc1c(N2C[C@@H](C)N(C(=O)CCl)[C@@H](C)C2)c(F)cc2c(=O)c(C(=O)NCc3ccc(Cl)cc3Cl)cn(C3CC3)c12
compound
COc1c(N2C[C@@H](C)N(C(=O)CCl)[C@@H](C)C2)c(F)cc2c(=O)c(C(=O)NCc3ccc(Cl)cc3Cl)cn(C3CC3)c12
7-[(3R,5S)-4-(Chloroacetyl)-3,5-dimethylpiperazin-1-yl]-1-cyclopropyl-N-(2,4-dichlorobenzyl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide
[N-]=[N+]=[N-].[Na+]
sodium azide

Reactivos

Ninguno

Disolventes

CN(C)C=O
N,N-dimethylformamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter fine purification by preparative RP-HPLC (Method 6) 46 mg of the target compound
  2. 2
    Otroare obtained

Procedimiento

50.0 mg of the compound of Example 80A and 15.6 mg (0.24 mmol) of sodium azide are stirred in 3 ml of N,N-dimethylformamide in a closed reaction vessel at 90° C. over night. After fine purification by preparative RP-HPLC (Method 6) 46 mg of the target compound are obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07867992B2uspto-grants-2011_01