Pyridine → HCID 22622556, compound

HRID 1604383Notes

Reaction equation

HRID 1604383 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17](O)=O)=[CH:13][CH:12]=1)[CH2:9][CH3:10].CS(Cl)(=O)=O.[N:31]1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]#[N:31])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 22622527HCID 22622527, compound

Product 1

HCID 22622556HCID 22622556, compound

Conditions

Temperature
4 °C

Procedure

6-[N-(5-Chloro-2-(2-methylpropoxy )benzyl)-N-ethylamino]pyridazine-3-carboxylic acid (example 10) (2.0 g) was dissolved in pyridine (30 ml) under argon and cooled to 4° C. Methanesulphonyl chloride (0.75 ml, 9.7 mmol) was added to the mixture which was stirred at 4° C. for 1.5 hours to give a dark purple solution. Ammonia gas was then bubbled through the solution for 2 minutes to give a dark red solution (exotherm to +15° C.) and the solution evaporated under reduced pressure. The residue was dissolved in pyridine (30 ml) and cooled under argon to 4° C. Methanesulphonyl chloride (5.1 ml, 66 mmol) was then added dropwise (exotherm to 10° C.) and the resultant brown suspension stirred at ambient temperature overnight. The brown solution was then evaporated and the residue partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with 10% 2N HCl/saturated aqueous ammonium chloride (×2), saturated aqueous sodium bicarbonate (×1) and brine (×1), dried over Na2SO4, filtered and evaporated. The title product was isolated by column chromatography using 20% ethyl acetate/isohexane as eluant (1.18 g, 62.2%). [OPPI 14: 396-9 (1982)].

Workup

  1. customto give a dark purple solution
  2. customAmmonia gas was then bubbled through the solution for 2 minutes
  3. customto give a dark red solution (exotherm to +15° C.)
  4. customthe solution evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in pyridine (30 ml)
  6. temperaturecooled under argon to 4° C
  7. stirringthe resultant brown suspension stirred at ambient temperature overnight
  8. customThe brown solution was then evaporated
  9. customthe residue partitioned between saturated aqueous ammonium chloride and ethyl acetate
  10. washThe organic layer was washed with 10% 2N HCl/saturated aqueous ammonium chloride (×2), saturated aqueous sodium bicarbonate (×1) and brine (×1)
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-e97ee4af737146f581b62c66c562c56a
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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