Hydrochloric Acid → HCID 46182771, compound

HRID 1468802Notes

Reaction equation

HRID 1468802 reaction equation
[Na].C[O:3][C:4](=O)[CH2:5][C:6]1=[N:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9](=[O:21])/[C:10]/1=[C:11](/[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)\[CH3:12].Cl>CC(O)C>[CH2:22]([N:8]1[C:9](=[O:21])[C:10]2=[C:11]([CH3:12])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:4](=[O:3])[CH:5]=[C:6]2[NH:7]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 178499644HCID 178499644, compound

Product 1

HCID 46182771HCID 46182771, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An isopropanolic solution of i-PrONa, obtained by dissolving of sodium (0.017 g, 0.713 mmol, 1 equiv) in i-PrOH (16 ml), was treated with methyl[(4E)-1-benzyl-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]ethylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) (0.270 g, 0.713 mmol, 1 equiv.). The reaction mixture was refluxed for 1 h, then cooled and neutralized to pH 7 by addition of 0.12 ml of a 20% aqueous HCl solution. 15 ml of i-PrOH were removed in vacuo and 10 ml of H20 were added before placing the flask in the fridge overnight. The white precipitate formed was filtered off, washed with water (2×3 ml), then with cyclohexane and dried in vacuo. 0.240 g of pure product 2-benzyl-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione was obtained. Yield 97%. 1H NMR (500 MHz, DMSO-d6, ppm) 2.78 (s, 3H), 4.81 (s, 2H), 5.37 (s, 2H), 5.59 (s, 1H), 7.31-7.26 (m, 5H), 7.36 (m, 2H), 7.76 (td, J 7.6, 1.9 Hz, 1H), 8.46 (dt, J 4.2, 1.6 Hz, 1H), 10.34 (s, 1H); MS (ESI+)=347.2.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. temperaturecooled
  3. custom15 ml of i-PrOH were removed in vacuo and 10 ml of H20
  4. additionwere added
  5. customin the fridge overnight
  6. customThe white precipitate formed
  7. filtrationwas filtered off
  8. washwashed with water (2×3 ml)
  9. dry with materialwith cyclohexane and dried in vacuo

Sources & evidence

ORD record
ord-1ca3c9b06bbd49f9b15df54368ded085
Source dataset
uspto-grants-2015_04
Patent number
US09006238B2

Reaction notes

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