Pyridine → HCID 21183724, compound

HRID 1384824Notes

Reaction equation

HRID 1384824 reaction equation
N1C=CC=CC=1.O[CH2:8][C:9]1[C:21]2[C:20]3[CH:19]=[C:18]([CH3:22])[CH:17]=[CH:16][C:15]=3[N:14]([CH3:23])[C:13]=2[C:12](=[O:24])[N:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:10]=1.CS([Cl:35])(=O)=O.ClCCl>O1CCCC1>[Cl:35][CH2:8][C:9]1[C:21]2[C:20]3[CH:19]=[C:18]([CH3:22])[CH:17]=[CH:16][C:15]=3[N:14]([CH3:23])[C:13]=2[C:12](=[O:24])[N:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 21183760HCID 21183760, compound

Product 1

HCID 21183724HCID 21183724, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

50 ml of pyridine are added to a suspension of 9.5 g (29.7 mmol) of 1-(hydroxymethyl)-5,8-dimethyl-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indol-4-one in 600 ml of tetrahydrofuran heated to 60° C. 4.5 ml (59.4 mmol) of methanesulphonyl chloride are added and the mixture is left standing for 15 h at room temperature. 500 ml of dichloromethane are added, the precipitate is removed by filtration, separation is carried out by settling and the organic phase is washed with water. It is dried over sodium sulphate and the solvent is evaporated under reduced pressure. 5 g (14.8 mmol) of product are obtained, which product is used as is in the following stage.

Workup

  1. waitthe mixture is left
  2. customthe precipitate is removed by filtration, separation
  3. washthe organic phase is washed with water
  4. dry with materialIt is dried over sodium sulphate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-89e93adc666b45deac5d833f86be0e1b
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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