Sodium hydride → 3-(1-(4-Butoxymethyl-benzyl)-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 77866Notes

Reaction equation

HRID 77866 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.[H-].[Na+].[CH2:15]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH3:18]>CN(C)C=O>[CH2:15]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:1]2[CH:5]=[C:4]([C:6]3[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=3)[CH:3]=[N:2]2)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 592551091-Butoxymethyl-4-chloromethyl-benzeneHCID 592552903-(1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 167190853-(1-(4-Butoxymethyl-benzyl)-1H-pyrazol-4-yl)-pyridin-2-ylamineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(1H-pyrazol-4-yl)-pyridin-2-ylamine (20 mg, 0.13 mmol) described in Manufacturing Example 32-1-4 and N,N-dimethylformamide (1 mL) was added sodium hydride (6.8 mg, 0.19 mmol, 66% in oil), which was stirred for 30 minutes at room temperature. 1-Butoxymethyl-4-chloromethyl-benzene (29 mg, 0.14 mmol) described in Manufacturing Example 33-1-4 was added to the reaction mixture at room temperature, and stirred for 1.5 hours at 40° C. The reaction mixture was cooled and partitioned into water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the title compound (33 mg, 78%).

Workup

  1. additionwas added to the reaction mixture at room temperature
  2. stirringstirred for 1.5 hours at 40° C
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned into water and ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1)

Sources & evidence

ORD record
ord-e44e7ea6d75840fda40558ecd4283253
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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