Potassium Carbonate → HCID 178527240, compound

HRID 2414547Notes

Reaction equation

HRID 2414547 reaction equation
C(OC(=O)[CH2:5][NH:6][S:7](C1C=CC(OCC#CC)=CC=1)(=[O:9])=[O:8])C.C(=O)([O-])[O-].[K+].[K+].Cl.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](CCl)[CH:30]=1>CN(C=O)C.CCOCC.O>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=1[CH2:5][NH:6][SH:7](=[O:9])=[O:8]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 54356225(4-But-2-ynyloxy-benzenesulfonylamino)-acetic acid ethyl ester

Product 1

HCID 178527240HCID 178527240, compoundYield 201%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.300 g (0.965 mmol) of the product of Example 20 in 5.0 mL of DMF was added 0.419 g (3.038 mmol) of potassium carbonate followed by 0.166 g (1.013 mmol) of 3-picolyl chloride hydrochloride. The resulting mixture was stirred at room temperature for 15 h and then diluted with ether and water. The organics were washed with water, dried over Na2SO4, filtered and concentrated in vacuo to give a pale yellow solid. The solid was washed with ether/hexanes (1:1) and dried in vacuo to provide 0.334 g (86%) of the N-picolyl sulfonamide as a tan solid. Electrospray Mass Spec 402.9 (M+H)+

Workup

  1. washThe organics were washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. washThe solid was washed with ether/hexanes (1:1)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7b5e0cd26edb4932919ff6430152c830
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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