Methanesulfonyl chloride → HCID 22141253, compound

HRID 428863Notes

Reaction equation

HRID 428863 reaction equation
[CH2:1]([N:4]1[CH2:9][CH:8]2[CH:6]([C:7]2([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])[CH3:10])[CH2:5]1)[CH:2]=[CH2:3].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH2:1]([N:4]1[CH2:5][CH:6]2[CH:8]([C:7]2([C:11]2[CH:12]=[C:13]([NH:14][S:19]([CH3:18])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)[CH3:10])[CH2:9]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22141153HCID 22141153, compound

Product 1

HCID 22141253HCID 22141253, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3-(3-allyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)aniline (Preparation 52, 8.5 g, 37.2 mmol) dissolved in pyridine (70 ml) at 0° C. was added methanesulphonyl chloride (4.32 ml, 55.8 mmol) dropwise over 20 min. The reaction mixture was allowed to stir for 16 h and was then quenched with ice (5 g). The reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane and washed with saturated aqueous sodium hydrogen carbonate solution, followed by water. The organic extracts were concentrated in vacuo and then purified by flash chromatography on silica gel, eluting with ethyl acetate:dichloromethane:2N ammonia in methanol (30:69:1). The product was obtained as a viscous brown oil (7.7 g, 68%).

Workup

  1. customwas then quenched with ice (5 g)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution
  5. concentrationThe organic extracts were concentrated in vacuo
  6. custompurified by flash chromatography on silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e2318eb93252465eb41dc6262d507f5c
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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