تفاعل #1340632

معادلة التفاعل

HCl

methyl[(4Z)-1-methyl-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]pentylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate

sodium

→

pure product

المردود 80.0%

4-butyl-2-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione

المردود 80.0%

المذيبات

i-PrOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed for 1 h
2. 2
   درجة الحرارةcooled
3. 3
   أخرى50 ml of i-PrOH were removed in vacuo and 25 ml of H2O
4. 4
   workup.ADDITIONwere added
5. 5
   أخرىin the fridge overnight
6. 6
   أخرىThe white precipitate formed
7. 7
   ترشيحwas filtered off
8. 8
   غسيلwashed with water (2×5 ml)
9. 9
   تجفيفwith cyclohexane and dried in vacuo

الإجراء التجريبي

An isopropanolic solution of i-PrONa, obtained by dissolving of sodium (0.082 g, 3.57 mmol, 1 equiv.) in i-PrOH (75 ml), was treated with methyl[(4Z)-1-methyl-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]pentylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) (0.61 g, 3.57 mmol, 1 equiv.). The reaction mixture was refluxed for 1 h, then cooled and neutralized to pH 7 by addition of 0.59 ml of a 20% aqueous HCl solution. 50 ml of i-PrOH were removed in vacuo and 25 ml of H2O were added before placing the flask in the fridge overnight. The white precipitate formed was filtered off, washed with water (2×5 ml), then with cyclohexane and dried in vacuo. 0.88 g of pure product 4-butyl-2-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione was obtained. Yield 80%. 1HNMR (DMSO-d6, 400 MHz): 0.80 (3H, t, J=7.2 Hz); 1.29-1.35 (2H, m); 1.38-1.43 (2H, m); 3.19 (3H, s); 3.22-3.24 (2H, m); 5.49 (2H, s); 5.72 (1H, s); 7.42 (1H, d, J=8 Hz); 7.62 (1H, t, J=6.6 Hz); 8.12 (1H, t, J=8 Hz); 8.65 (1H, d, J=5.2 Hz). MS (ESI+): 313.4; MS (ESI−): 311.3.

المصدر