تفاعل #6972

معادلة التفاعل

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

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

triethylsilane

→

title compound

المردود 47.3%

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

المردود 47.3%

المذيبات

TFA DCM

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for 1 h
2. 2
   تركيزconcentrated
3. 3
   أخرىThe precipitates were collected
4. 4
   غسيلwashed with water
5. 5
   أخرىdried
6. 6
   أخرىThe solid was triturated with MeOH
7. 7
   ترشيحfiltered

الإجراء التجريبي

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).

المصدر