2'-Methoxyacetophenone → HCID 178489295, Verbindung

DIPEA (99 mg, 0.76 mmol) was added to a stirred solution {[5-(2-methoxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (60 mg, 0.22 mmol) (prepared by the method used for the synthesis of Intermediate 30, starting from (2′-methoxy)acetophenone) in DMF (2.0 mL) followed by HOBt (34 mg, 0.25 mmol) and EDCI.HCl (49 mg, 0.25 mmol). After 2 minutes of stirring, (2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride (54 mg, 0.22 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine and concentrated. The residue was purified washing with diethyl ether to afford 67 mg (43.5% Yield) of 5-(2-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 468.2, 98.33%. 1H NMR (300 MHz, DMSO-d6): δ13.6 (S, 1H), 8.05 (m, 1H), 7.7 (m, 1H), 7.35 (m, 1H), 7.24 (m, 1H), 7.12 (m, 2H), 7.0 (m, 2H), 6.82 (m, 1H), 4.85 (d, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.9 (s, 3H), 3.85 (m, 1H), 3.6 (m, 1H), 3.1 (m, 1H), 2.7 (m, 1H), 1.9 (m, 2H), 1.4 (m, 2H).

1. customprepared by the method
2. stirringstirring
3. waitwas continued at ambient temperature overnight
4. extractionextracted with ethyl acetate
5. washwashed with brine
6. concentrationconcentrated
7. customThe residue was purified
8. washwashing with diethyl ether

ORD-Eintrag

ord-ca06ae21cd8d44ee8efe29e3a148f0e3

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08129376B2