Hydrochloric Acid → 6-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]-3-cyanopyridazine

HRID 1870774

Reaction equation

HRID 1870774 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([NH2:19])=O)=[CH:13][CH:12]=1)[CH2:9][CH3:10].CS(Cl)(=O)=O.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]#[N:19])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 186932586-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide

Product 1

HCID 186932386-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]-3-cyanopyridazineYield 126.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-[N-(5-chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]-pyridazine-3-carboxamide (example 18) (210 mg, 0.6 mmol) in pyridine (10 ml) at 0° C. was added methane sulfonyl chloride (0.5 ml, 0.6 mmol) and the mixture allowed to stir (gradually coming to an ambient temperature as the ice melts) for 60 hours. The solution was poured into 2 N hydrochloric acid (50 ml) over ice and the product extracted with diethyl ether (200 ml), washed with water (3×200 ml), dried over anhydrous magnesium sulphate and the solvent removed in vacuo to give the title compound as a brown gum (260 mg) which was used without further purification.

Workup

  1. customfor 60 hours
  2. extractionthe product extracted with diethyl ether (200 ml)
  3. washwashed with water (3×200 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-28fd233580a849cf9c7979c101dbe3ca
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Linked notes

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