Reacción #6972

Ecuación de reacción

2-[pyridin-2-ylamino]-thiazole-5-carbaldehyde

5-amino-N-cyclopropyl-2,4-difluorobenzamide

triethylsilane

→

title compound

Rendimiento 47.3%

N-Cyclopropyl-2,4-difluoro-5-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzamide

Rendimiento 47.3%

Disolventes

TFA DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 1 h
2. 2
   Concentraciónconcentrated
3. 3
   OtroThe precipitates were collected
4. 4
   Lavadowashed with water
5. 5
   Otrodried
6. 6
   OtroThe solid was triturated with MeOH
7. 7
   Filtraciónfiltered

Procedimiento

A mixture of 2-[pyridin-2-ylamino]-thiazole-5-carbaldehyde (41.0 mg, 0.2 mmol) and 5-amino-N-cyclopropyl-2,4-difluorobenzamide (46.6 mg, 0.22 mmol) in TFA/DCM (1:1, 1 mL) was stirred at RT for 10 min and triethylsilane (0.1 mL) was added. The mixture was stirred for 1 h, then concentrated and the residue was neutralized with NaHCO3 solution and the precipitates occurred. The precipitates were collected, washed with water and dried. The solid was triturated with MeOH and filtered to afford the title compound as a grayish solid (38 mg, 47%). Small amount of solid was boiled in methanol, the mixture was cooled to RT and filtered to afford a white solid. MS m/z 402 (M+H)+. 1H NMR (DMSO-d6) δ 8.23 (d, 1H, J=4.0 Hz), 8.15 (s, 1 H), 7.65 (t, 1 H, J=7.15 Hz), 7.26 (s, 1 H), 7.16 (m, 1 H), 7.01 (d, 1 H, J=8.75 Hz), 6.95 (m, 1 H), 6.89 (t, 1 H, J=7.15 Hz), 6.12 (s 1 H), 4.43 (m, 2 H), 2.79 (m, 1 H), 0.69 (m, 2 H), 0.51 (m, 2 H).

Fuente