Hydrochloric Acid → Gkt-136901

HRID 447892Notes

Reaction equation

HRID 447892 reaction equation
[Na].C[O:3][C:4](=O)[CH2:5][C:6]1=[N:7][N:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[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>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 178499640HCID 178499640, compound

Product 1

HCID 17027464Gkt-136901Yield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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[(4E)-1-(2-chlorophenyl)-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]ethylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) (1.42 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. 1.07 g of pure product 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione was obtained. Yield 82%. 1H-NMR: (500 MHz, DMSO-d6, ppm): 2.78 (s, 3H), 5.41 (s, 2H), 5.66 (s, 1H), 7.31-7.28 (m, 1H), 7.32 (d, J=7.9 Hz, 1H), 7.50-7.47 (m, 2H), 7.60-7.56 (m, 1H), 7.66-7.64 (m, 1H), 7.79 (td, J 7.6, 1.9 Hz, 1H), 8.48 (m, 1H), 10.73 (s, br, 1H). MS (ESI+): 367.9; MS (ESI−): 365.7.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. temperaturecooled
  3. custom50 ml of i-PrOH were removed in vacuo and 25 ml of H2O
  4. additionwere added
  5. customin the fridge overnight
  6. customThe white precipitate formed
  7. filtrationwas filtered off
  8. washwashed with water (2×5 ml)
  9. dry with materialwith cyclohexane and dried in vacuo

Sources & evidence

ORD record
ord-fcf379bab02e4cea9007cdf0e231a62a
Source dataset
uspto-grants-2013_07
Patent number
US08481562B2

Reaction notes

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