Dichloromethane → HCID 18182379, compound

HRID 1359329Notes

Reaction equation

HRID 1359329 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]([F:33])([F:32])[S:8]([O:11][C:12]1[C:13]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:14][C:15]([C:18]2(O)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:16][CH:17]=1)(=[O:10])=[O:9].C(N(CC)CC)C.ClCCl>C(OCC)(=O)C.O>[F:33][C:7]([F:6])([F:32])[S:8]([O:11][C:12]1[C:13]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:14][C:15]([C:18]2[CH2:23][CH2:22][O:21][CH2:20][CH:19]=2)=[CH:16][CH:17]=1)(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18182497HCID 18182497, compound

Product 1

HCID 18182379HCID 18182379, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

57.9 μl of methanesulfonyl chloride was added dropwise to a mixture of 104 mg of 2-benzyl-6-(4-hydroxytetrahydro-4H-pyran-4-yl)-3-pyridyl trifluoromethane sulfonate, 139 μl of triethylamine and 2 ml of dichloromethane under ice-cooling. After stirring at room temperature for 3 hours, water and ethyl acetate were added thereto. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 15% ethyl acetate/hexane, to give 60.7 mg of the target compound.

Workup

  1. temperaturecooling
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-1295fc5b35de4bfeae922f46a3dde5a3
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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