Reaktion #1181010

Reaktionsgleichung

HOBt

(2′-methoxy)acetophenone

EDCI.HCl

(2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride

DIPEA

{[5-(2-methoxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid

→

5-(2-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

Ausbeute 65.1%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared by the method
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued at ambient temperature overnight
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Waschenwashed with brine
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified
8. 8
   Waschenwashing with diethyl ether

Vorschrift

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).

Quelle