Hydrochloric Acid → HCID 46182771, compound

HRID 1253441Notes

Reaction equation

HRID 1253441 reaction equation
[Na].[CH2:2]([N:9]1[C:13](=[O:14])/[C:12](=[C:15](/[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)\[CH3:16])/[C:11]([CH2:25][C:26]([O:28]C)=O)=[N:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CC(O)C>[CH2:2]([N:9]1[C:13](=[O:14])[C:12]2=[C:15]([CH3:16])[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:26](=[O:28])[CH:25]=[C:11]2[NH:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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 H2O 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+1)=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 H2O
  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-2ec6552b23a448d8b5be9120cf6b5e6c
Source dataset
uspto-grants-2013_06
Patent number
US08455486B2

Reaction notes

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