1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → HCID 21836533, compound

HRID 1739738Notes

Reaction equation

HRID 1739738 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][S:24]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)(=[O:26])=[O:25]>C(#N)C>[NH2:23][S:24]([N:27]1[CH2:32][CH2:31][N:30]([CH:10]2[CH2:9][N:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:11]2)[CH2:29][CH2:28]1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 112521981-Piperazinesulfonamide

Product 1

HCID 21836533HCID 21836533, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (see Preparation 54) (4.8 g, 15.1 mmol) and 1-aminosulphonylpiperazine (see Example 123(f)) (5 g) in acetonitrile (50 ml) was heated under reflux for 4 hours. The reaction was cooled and the solid filtered off and washed with acetonitrile (50 ml). The filtrate was concentrated under reduced pressure and the residue slurried in hot toluene (50 ml), cooled, the solid filtered off and washed with toluene (50 ml). The product was then further purified by slurrying in hot ethyl acetate (3 ml), cooling and filtering to give the title compound (0.47 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe solid filtered off
  4. washwashed with acetonitrile (50 ml)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. temperaturethe residue slurried in hot toluene (50 ml), cooled
  7. filtrationthe solid filtered off
  8. washwashed with toluene (50 ml)
  9. customThe product was then further purified
  10. temperaturecooling
  11. filtrationfiltering

Sources & evidence

ORD record
ord-911af1a100ac4763a5494b3269ad23cf
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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