1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874477, Verbindung

DIPEA (149.2 mg, 1.15 mmol) was added to a stirred solution of 1-(3,5-difluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (65 mg, 0.28 mmol) in DMF (2 mL) followed by HOBt (43 mg, 0.31 mmol) and EDCI (110 mg, 0.57 mmol). After 2 minutes of stirring, 2-amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (88.4 mg, 0.28 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected. The crude solid was purified by recrystallisation from a mixture of DCM and hexane to afford 95 mg (54.4% Yield) of 1-(3,5-difluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 477.12, 98.45%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 8.5 (t, 1H), 8.3 (d, 1H), 8.2 (d, 1H), 7.9 (d, 2H), 7.75 (t, 1H), 7.58-7.5 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 4.0-3.8 (m, 1H), 3.8-3.6 (m, 1H), 3.4 (m, 1H), 3.2 (m, 1H), 2.1-1.9 (m, 2H), 1.9-1.5 (m, 2H).

1. additionwas added
2. stirringthe resulting mixture was stirred at room temperature overnight
3. customthe precipitate was collected
4. customThe crude solid was purified by recrystallisation from a mixture of DCM and hexane

ORD-Eintrag

ord-83e300a1dc684632804cdecb1e9e8bb1

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08129376B2