Chloroform → HCID 22452248, compound

HRID 2185821Notes

Reaction equation

HRID 2185821 reaction equation
[NH2:1][C:2]1[C:3](=[O:23])[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:16]([N:4]1[C:3](=[O:23])[C:2]([N:1]([S:32]([CH3:31])(=[O:34])=[O:33])[S:32]([CH3:31])(=[O:34])=[O:33])=[CH:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)=[N:5]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22452192HCID 22452192, compound

Product 1

HCID 22452248HCID 22452248, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-amino-2-benzyl-6-(4-methoxyphenyl)-2H-pyridazin-3-one (60 mg, 0.20 mmol) and triethylamine (80 mg, 0.79 mmol) in toluene (1 ml), methanesulfonyl chloride (70 mg, 0.61 mmol) was added, followed by heating under stirring at 40° C. for 1 hour. Chloroform was added to the reaction mixture. The organic layer was washed with water and brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was separated and purified by silica gel preparative chromatography [developer: hexane/ethyl acetate (1/1)], whereby the title compound (76 mg, 90.4%) was obtained.

Workup

  1. temperatureby heating
  2. washThe organic layer was washed with water and brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was separated
  6. custompurified by silica gel preparative chromatography [developer: hexane/ethyl acetate (1/1)], whereby the title compound (76 mg, 90.4%)
  7. customwas obtained

Sources & evidence

ORD record
ord-5a9597953510456ebed9b0f2eede7696
Source dataset
uspto-grants-2002_06
Patent number
US06403586B1

Reaction notes

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