Acetic Acid → 1-(2,4-Dimethoxyphenyl)-N-{[1-(4-iodophenyl)-3-phenyl-1H-pyrazol-4-yl]methyl}methanamine

HRID 2383353Notes

Reaction equation

HRID 2383353 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH:13]=O)[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH:26][CH2:13][C:11]1[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)[CH:12]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 574369251-(4-Iodophenyl)-3-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 581121691-(2,4-Dimethoxyphenyl)-N-{[1-(4-iodophenyl)-3-phenyl-1H-pyrazol-4-yl]methyl}methanamineYield 100.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1.34 g (3.581 mmol) of the product from Example 2A and 538 μl (3.581 mmol) of 2,4-dimethoxybenzylamine are dissolved in 40 ml of dichloroethane, and the mixture is stirred at room temperature for one hour. 1.52 g (7.162 mmol) of sodium triacetoxyborohydride and 820 μl (14.33 mmol) of glacial acetic acid are then added. The reaction mixture is stirred at room temperature for 15 hours. A saturated sodium bicarbonate solution is then added, and the product is extracted with dichloromethane. The organic extract is washed with water and dried over anhydrous sodium sulphate. After filtration, the solvent is removed on a rotary evaporator. The crude product is dried under high vacuum and used without further purification in the next reaction. What is obtained are 1.89 g of the title compound.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 15 hours
  2. extractionthe product is extracted with dichloromethane
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationAfter filtration
  7. customthe solvent is removed on a rotary evaporator
  8. dry with materialThe crude product is dried under high vacuum
  9. customused without further purification in the next reaction
  10. customWhat is obtained

Sources & evidence

ORD record
ord-b40418d3d3c14790872c3254466e6f09
Source dataset
uspto-grants-2012_09
Patent number
US08263624B2

Reaction notes

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