Triethylamine → HCID 86674652, Verbindung

Temperatur

0 °C

A stirred solution of trichloromethyl carbonochloridate (1.038 g, 5.25 mmol) in tetrahydrofuran (10 mL) was cooled to 0° C. and a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (1 g, 4.37 mmol, J. Med. Chem., 2005, 141) and N-ethyl-N-isopropylpropan-2-amine (1.131 g, 8.75 mmol) in tetrahydrofuran (10 mL) was added slowly in 25 minutes. After stirring at 0° C. for one hour the solids were removed by filtration and the filtrate was concentrated in vaccuo (50° C. bath temperature). The residue was added to a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (0.788 g, 4.37 mmol) and triethylamine (1.018 g, 10.06 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred for three hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Purification using column chromatography (silica gel; gradient dichloromethane/methanol 100:0 to 95:5) to afford N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (1.56 g, 4.31 mmol, 99% yield). LC-MS: C12H11ClF3N7O: 361. found 362.04[M+H]+, RT=0.42 min.

1. customwere removed by filtration
2. concentrationthe filtrate was concentrated in vaccuo (50° C. bath temperature)
3. stirringthe reaction mixture was stirred for three hours
4. customThe solids were removed by filtration
5. concentrationthe filtrate was concentrated in vacuo
6. customPurification

ORD-Eintrag

ord-3c34b64f6ed44ffa95a8318344aab70b

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09446130B2