Diisopropylethylamine → HCID 86641647, compound

To a stirred solution of (1-benzyl-piperidin-4-yl)-(4-trifluoromethyl-thiazol-2-yl)-amine (D8) (0.57 g, 1.68 mmol) and diisopropylethylamine (1.04 ml, 5.88 mmol) in dichloromethane (15 ml) at 0° C., was added 1-chloroethyl chloroformate (0.45 ml, 4.2 mmol). The reaction mixture was stirred at room temperature for 3 h. and after this period, diluted with dichloromethane and extracted with a saturated solution of sodium hydrogen carbonate (5 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was dissolved in methanol (5 ml) and the reaction mixture was stirred at reflux for 3 h. After evaporation of the solvent, the crude product was purified by column chromatography (silica gel; 5-8% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The crude product was crystallized from acetonitrile to yield D9 (0.34 g, 81%) as a white solid. C9H12F3N3S requires 251. Found 252 (MH+).

1. extractionextracted with a saturated solution of sodium hydrogen carbonate (5 ml)
2. customThe organic layer was separated
3. dry with materialdried (Na2SO4)
4. customthe solvent evaporated in vacuo
5. dissolutionThe crude product was dissolved in methanol (5 ml)
6. stirringthe reaction mixture was stirred
7. temperatureat reflux for 3 h
8. customAfter evaporation of the solvent
9. customthe crude product was purified by column chromatography (silica gel; 5-8% ammonia in methanol (7M)/dichloromethane)
10. customThe desired fractions were collected
11. customevaporated in vacuo
12. customThe crude product was crystallized from acetonitrile

ORD record

ord-4217836626da4f548caf4a14d6cffaa0

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933101B2