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

HRID 1831668Notes

Reaction equation

HRID 1831668 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 silca 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 silca gel column chromatography

Sources & evidence

ORD record
ord-485e828c9d5c474aac04bad50511389b
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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