3,6-Dichloropyridazine → HCID 87205336, compound

HRID 1426064Notes

Reaction equation

HRID 1426064 reaction equation
C[Si](N)(C)C.[K].[N:7]12[CH2:15][CH:11]([CH2:12][CH2:13][CH2:14]1)[CH:10]([OH:16])[CH2:9][CH2:8]2.[Cl:17][C:18]1[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=1>C1COCC1>[Cl:17][C:18]1[N:19]=[N:20][C:21]([O:16][CH:10]2[CH:11]3[CH2:15][N:7]([CH2:14][CH2:13][CH2:12]3)[CH2:8][CH2:9]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 673313,6-DichloropyridazineHCID 189861071-Azabicyclo[3.3.1]nonan-4-olHCID 87205400HCID 87205400, compound

Product 1

HCID 87205336HCID 87205336, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Potassium trimethylsilylamine (5.25 mmol) is added to a solution of (rac.)-1-Aza-bicyclo[3.3.1]nonan-4-ol (5.0 mmol) in THF (20 ml) at room temperature and the solution is stirred for 30 min. The resulting potassium alcoholate is slowly added to a precooled solution of 3,6-dichloropyridazine (7.5 mmol) in THF (50 ml) and the resulting mixture is stirred for another 20 minutes. The solution is allowed to warm to 0° C. is quenched with brine and extracted with diethylether. The organic layer is dried over magnesium sulfate and evaporated. The brown oil is purified by silica gel column chromatography (CH2Cl2:MeOH:NH3, 9:1:0.1) to afford (rac.)-4-(6-Chloro-pyridazin-3-yloxy)-1-aza-bicyclo[3.3.1]nonane (320 mg).

Workup

  1. stirringthe resulting mixture is stirred for another 20 minutes
  2. customis quenched with brine
  3. extractionextracted with diethylether
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. customevaporated
  6. customThe brown oil is purified by silica gel column chromatography (CH2Cl2:MeOH:NH3, 9:1:0.1)

Sources & evidence

ORD record
ord-be5ca66136f74da0bc8a7f867ef31385
Source dataset
uspto-grants-2015_01
Patent number
US08933090B2

Reaction notes

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