HCID 178418582, compound → HCID 58358242, compound

HRID 1468804Notes

Reaction equation

HRID 1468804 reaction equation
CO[Na].C[O:5][C:6](=O)[CH2:7][C:8]1=[N:9][N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:11](=[O:31])/[C:12]/1=[C:13](\[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)/[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1>CO>[CH2:32]([N:10]1[C:11](=[O:31])[C:12]2=[C:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:6](=[O:5])[CH:7]=[C:8]2[NH:9]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 178418582HCID 178418582, compoundHCID 178499643HCID 178499643, compound

Product 1

HCID 58358242HCID 58358242, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above obtained methyl[(4Z)-1-benzyl-4-{2-(3-methoxyphenyl)-1-[(pyridin-2-yl methyl)amino]ethylidene}-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) was treated with freshly prepared MeONa in MeOH (2M, 20 ml). The solution was stirred at room temperature until disappearance of the starting enamine (t=0.5-2 h). The reaction mixture was concentrated in vacuum to eliminate MeOH and the crude was dissolved in ethyl acetate (80 ml), extracted with water (30 ml*3). Then the combined inorganic layer was acidified to pH=6, extracted with ethyl acetate (30 ml*3), the combined organic layer was dried over Na2SO4, purified by TLC yielding the final product 2-benzyl-4-(3-methoxybenzyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione as yellow oil (65 mg, yield: 43%). 1HNMR (400 MHz, DMSO-d6): 3.635 (s, 3H); 4.702 (s, 2H); 4.860 (s, 2H); 5.274 (s, 2H), 5.696 (s, 1H); 6.646-6.716 (m, 3H), 7.104-7.144 (m, 2H); 7.277-7.416 (m, 6H); 7.823-7.859 (t, 1H); 8.492-8.501 (d, 1H). MS(ESI+): 453.2; MS(ESI−): 451.2.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. dissolutionthe crude was dissolved in ethyl acetate (80 ml)
  3. extractionextracted with water (30 ml*3)
  4. extractionextracted with ethyl acetate (30 ml*3)
  5. dry with materialthe combined organic layer was dried over Na2SO4
  6. custompurified by TLC

Sources & evidence

ORD record
ord-042e0f70c6c14fa9a2f9c19f074f91a7
Source dataset
uspto-grants-2015_04
Patent number
US09006238B2

Reaction notes

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