Sodium hydride → HCID 86710540, compound

HRID 1027145Notes

Reaction equation

HRID 1027145 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[H-].[Na+].[Cl:14][C:15]1[N:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=1>CN(C=O)C.CCOC(C)=O>[Cl:14][C:15]1[N:16]=[N:17][C:18]([O:8][CH:6]2[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3][C:2]([CH3:11])([CH3:1])[CH2:7]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 86710540HCID 86710540, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,2,6,6-tetramethylpiperidin-4-ol (106 mg, 0.67 mmol) in DMF (6.7 mL) was added 60% wt NaH (35 mg, 0.87 mmol). The solution was stirred at RT for 30 min, then 3,6-dichloropyridazine (100 mg, 0.67 mmol) was added and the reaction was stirred for 1 h. The crude reaction mixture was diluted in EtOAc. The organic layer was washed with water (5×), brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-chloro-6-(2,2,6,6-tetramethylpiperidin-4-yloxy)pyridazine, intermediate 1-3 (135 mg). The crude material used without further purification. LCMS Rt=1.22 min (condition B); MS (M+1)=270.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.53 (s, 1H), 7.37 (d, J=9.1 Hz, 1H), 6.91 (d, J=9.1 Hz, 1H), 5.68-5.78 (m, 1H), 2.20 (dd, J=12.4, 4.0 Hz, 2H), 1.32 (s, 6H), 1.27-1.29 (m, 2H), 1.20 (s, 6H).

Workup

  1. stirringthe reaction was stirred for 1 h
  2. customThe crude reaction mixture
  3. washThe organic layer was washed with water (5×), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-773c7ab3b55b4b98b23e8b91a15e7872
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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