HCID 21912443, compound → 2-(4-chloro-2,6-dimethylphenoxy)-3,6-dimethyl-N-(pentan-3-yl)pyridin-4-amine

HRID 1760680Notes

Reaction equation

HRID 1760680 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([CH3:24])[C:5]([O:6][C:7]2[C:12]([CH2:13]Cl)=[C:11]([NH:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:10]=[C:9]([CH3:21])[N:8]=2)=[C:4]([CH3:25])[CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]([O:6][C:7]2[C:12]([CH3:13])=[C:11]([NH:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:10]=[C:9]([CH3:21])[N:8]=2)=[C:22]([CH3:24])[CH:23]=1

Participants

3

Reactant 1

HCID 21912443HCID 21912443, compound

Product 1

HCID 104053732-(4-chloro-2,6-dimethylphenoxy)-3,6-dimethyl-N-(pentan-3-yl)pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2-(4-Chloro-2,6-dimethyl-phenoxy)-3-chloromethyl-6-methyl-pyridin-4-yl]-(1-ethyl-propyl)-amine (75 mg, 0.196 mmol) in dry THF was added 1.0M BH3 in THF (0.59 ml, 0.59 mmol) and stirred for 2 hr. The mixture was quenched with dilute HCl and stirred for 5 min. The reaction mixture was neutralized with 2N NaOH, water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography to give the title compound as a colorless oil.

Workup

  1. customThe mixture was quenched with dilute HCl
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-5e5816f94e4844828cc902de551d8fa2
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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