Reacción #90384

ord-fb647c98bcfa4087a2d33e9363b996e7

Ecuación de reacción

CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
VII
CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
(E)-N′-(2,7-dicyanobenzo[d]thiazol-6-yl)-N,N-dimethylformimidamide
Nc1ccc(F)c(Cl)c1
3-chloro-4-fluoroaniline
[Br-].[K+]
KBr
→
N#Cc1nc2ccc3ncnc(Nc4ccc(F)c(Cl)c4)c3c2s1
9-(3-Chloro-4-fluorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile
Rendimiento 64.0%

Reactantes

CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
VII
CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
(E)-N′-(2,7-dicyanobenzo[d]thiazol-6-yl)-N,N-dimethylformimidamide
Nc1ccc(F)c(Cl)c1
3-chloro-4-fluoroaniline
[Br-].[K+]
KBr

Reactivos

Ninguno

Disolventes

CCOC(C)=O.ClCCl
DCM EtOAc

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Prepared from VII and 3-chloro-4-fluoroaniline. Flash chromatography eluent (DCM-EtOAc, 8:2). Yield: 64%; yellow solid; mp 252° C.; IR (KBr) νmax/cm−1 3456, 3015, 2970, 2946, 2229, 1642, 1441, 1153, 1129, 1051, 968, 903, 817, 774, 695; 19F NMR (282 MHz, DMSO-d6) δ −123.8; 1H NMR (300 MHz, DMSO-d6) δ 8.43 (d, 1H, J=9.0 Hz), 8.30 (s, 1H), 7.62 (m, 2H), 7.34 (m, 2H); HRMS calcd for C16H7N5SClF (M+H+): 356.0156, found 356.0167.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09446044B2uspto-grants-2016_09