Methanol → tert-Butyl [1-(6-methoxypyridazin-3-yl)piperidin-4-yl]carbamate

HRID 2421972Notes

Reaction equation

HRID 2421972 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Na].[CH3:23][OH:24]>O>[CH3:23][O:24][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 379672514-(Boc-amino)-1-(6-chloro-3-pyridazinyl)piperidine

Product 1

HCID 86625870tert-Butyl [1-(6-methoxypyridazin-3-yl)piperidin-4-yl]carbamateYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

tert-Butyl [1-(6-chloropyridazin-3-yl)piperidin-4-yl]carbamate (0.50 g, 1.60 mmol) was dissolved in dry MeOH (15 ml) and sodium metal (0.073 g, 3.20 mmol) dissolved in MeOH (5 ml) was added. The reaction mixture was heated at in a microwave reactor at 120° C. for 4 h. The mixture was diluted with water (500 ml) and extracted with EtOAc (200 ml). The organic phase was dried (Na2SO4), filtered and evaporated to yield the title compound (0.37 g, 75%).

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (200 ml)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7287a543af424e5b99c45b779645383d
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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