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

HRID 2239569Notes

Reaction equation

HRID 2239569 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-9b4b65b1e53d469cbdc18486f5b9bfaf
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

Loading…