Sodium hydride → HCID 178482539, compound

tert-Butyl 3-oxopiperazine-1-carboxylate (1.5 g) was dissolved in DMF (50 mL), and sodium hydride (0.3 g) was added thereto. With ice cooling, N-(4-chloromethyl-3-methyl-1,3-thiazol-2(3H)-ylidene)-N-methylamine hydrochloride (1.6 g) was added thereto, and the mixture was mixed at 80° C. for 3 hours. The solvent was distilled off, and the residue was poured into water, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off to give 1-(((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-4-yl)methyl)-2-piperazinone (1.7 g) as a pale brown oily matter (a crude product). The resulting oily matter was dissolved in concentrated hydrochloric acid (5 mL) and mixed at room temperature for 1 hour. After concentrating the reaction solution, the residue was dissolved in dichloromethane (30 mL), and triethylamine (1.4 mL) was added thereto. With ice cooling, 3-((6-chloro-2-naphthyl)sulfonyl)propionic acid (1.5 g), HOBt (0.84 g) and WSC (1.0 g) were added thereto, and the mixture was mixed at room temperature for 16 hours. The reaction solution was basified with an aqueous potassium carbonate solution, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified with a basic silica gel column to give the title compound (0.25 g) as a colorless powder.

1. additionthe mixture was mixed at 80° C. for 3 hours
2. distillationThe solvent was distilled off
3. additionthe residue was poured into water
4. extractionextracted with chloroform
5. dry with materialthe extract was dried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off

ORD record

ord-446d9376c3924c2a9acfdc2df30a206d

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07534887B2