Water → HCID 22141151, compound

HRID 1826342Notes

Reaction equation

HRID 1826342 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2.[CH3:24][N:25]([CH3:30])[S:26](Cl)(=[O:28])=[O:27].[OH2:31].ClCCl>N1C=CC=CC=1>[C:21]([OH:27])(=[O:31])[CH3:22].[CH3:24][N:25]([CH3:30])[S:26]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:2]2([CH3:1])[CH:3]3[CH:7]2[CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]3)[CH:18]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 83372Dimethylsulphamoyl chlorideHCID 11266768HCID 11266768, compound

Product 1

HCID 22141151HCID 22141151, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 8, 200 mg, 0.65 mmol) in pyridine (2 ml) under nitrogen at 0° C. was added dimethylsulfamoyl chloride (140 mg, 0.98 mmol), then the mixture was stirred at room temperature for 16 hours. Water (5 ml) and dichloromethane (5 ml) were added, and the mixture was stirred for 30 minutes. The organic phase was washed further with water (5 ml) for 30 minutes, separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica (10 g) column chromatography eluting with ethyl acetate:hexane:ammonia solution (0.880) (20:80:1 then 50:50:1). Product-containing fractions were combined and concentrated in vacuo. The residue was further purified by preparative HPLC (condition 4). Combination and evaporation of appropriate fractions gave the title compound as a pale brown solid (7 mg, 3%).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. washThe organic phase was washed further with water (5 ml) for 30 minutes
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica (10 g) column chromatography
  8. washeluting with ethyl acetate
  9. concentrationconcentrated in vacuo
  10. customThe residue was further purified by preparative HPLC (condition 4)
  11. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-65910ff0776e4acdb0b9b3cd0a435533
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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