Reaktion #6972

Reaktionsgleichung

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

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

triethylsilane

→

title compound

Ausbeute 47.3%

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

Ausbeute 47.3%

Lösungsmittel

TFA DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 1 h
2. 2
   Einengenconcentrated
3. 3
   SonstigeThe precipitates were collected
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried
6. 6
   SonstigeThe solid was triturated with MeOH
7. 7
   Filtrationfiltered

Vorschrift

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).

Quelle