4-Methoxybenzylamine → (6-Amino-4-methylpyridin-3-yl) [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411272Notes

Reaction equation

HRID 2411272 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH3:26])[C:7]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([C:18]4[CH:19]=[N:20][C:21](F)=[CH:22][C:23]=4[CH3:24])=[O:17])[CH2:12][CH2:11]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.COC1C=CC(C[NH2:34])=CC=1>O>[NH2:34][C:21]1[N:20]=[CH:19][C:18]([C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[C:6]([CH3:26])=[CH:5][C:4]([CH:1]4[CH2:3][CH2:2]4)=[CH:9][N:8]=3)[CH2:11][CH2:12]2)=[O:17])=[C:23]([CH3:24])[CH:22]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 58484562HCID 58484562, compound

Product 1

HCID 71252201(6-Amino-4-methylpyridin-3-yl) [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanoneYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (1.45 g) described in Preparation Example 140 and 4-methoxybenzylamine (1.12 g) was stirred at 100° C. for 5 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in dichloromethane (10 mL), trifluoroacetic acid (20 mL) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.07 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. dissolutionThe obtained residue was dissolved in dichloromethane (10 mL)
  6. additiontrifluoroacetic acid (20 mL) was added
  7. stirringthe mixture was stirred at room temperature overnight
  8. additionWater was added to the reaction mixture
  9. extractionthe mixture was extracted with dichloromethane
  10. washThe organic layer was washed with saturated brine
  11. customthe solvent was evaporated
  12. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-eca8707fe8f84ae984fe16e8126d7604
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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