Sodium Methoxide → HCID 178492264, compound

HRID 1743792Notes

Reaction equation

HRID 1743792 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:12][CH2:11]2)[CH3:9])=[CH:4][CH:3]=1.[CH3:22][O-:23].[Na+]>CC(N(C)C)=O>[CH3:20][N:19]([CH3:21])[CH2:18][C:17]#[C:16][C@H:13]1[CH2:14][CH2:15][C@H:10]([N:8]([C:5]2[N:6]=[N:7][C:2]([O:23][CH3:22])=[CH:3][CH:4]=2)[CH3:9])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178483456HCID 178483456, compound

Product 1

HCID 178492264HCID 178492264, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 92.1 mg (0.3 mmol) of trans-(6-Chloro-pyridazin-3-yl)-[4-(3-dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-amine in 0.6 ml DMA was treated with 0.56 ml (3 mmol) of sodium methylate (5.4 M in MeOH) and heated at 80° C. for 54 h. The reaction was extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried (Na2SO4), filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 97:3) yielded 67 mg (74%) of pure trans-[4-(3-Dimethylamino-prop-1-ynyl)-cyclohexyl]-(6-methoxy-pyridazin-3-yl)-methyl-amine, MS: 303 (MH+).

Workup

  1. extractionThe reaction was extracted with aqueous saturated NaHCO3/Et2O (3×)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 97:3)

Sources & evidence

ORD record
ord-1d8e93c20da64aa5b2827c8e531b71b0
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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