HCID 178418582, compound → HCID 58358242, compound

HRID 1253443Notes

Reaction equation

HRID 1253443 reaction equation
CO[Na].[CH2:4]([N:11]1[C:15](=[O:16])/[C:14](=[C:17](\[NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)/[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)/[C:13]([CH2:35][C:36]([O:38]C)=O)=[N:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[CH2:4]([N:11]1[C:15](=[O:16])[C:14]2=[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[N:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:36](=[O:38])[CH:35]=[C:13]2[NH:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=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-ylmethyl)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-32700a13ffbc4d49916e4155ae34272a
Source dataset
uspto-grants-2013_06
Patent number
US08455486B2

Reaction notes

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