2-Thiophenesulfonyl chloride → HCID 53683563, compound

HRID 1858093Notes

Reaction equation

HRID 1858093 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([NH2:27])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[S:43](Cl)(=[O:45])=[O:44]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([NH:27][S:43]([C:39]3[S:38][CH:42]=[CH:41][CH:40]=3)(=[O:45])=[O:44])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:31]=[C:32]([CH3:37])[CH:33]=[C:34]([CH3:36])[CH:35]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 54025520HCID 54025520, compound

Product 1

HCID 53683563HCID 53683563, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (prepared essentially as described in Example 1, 200 mg in 10 mL pyridine) was added a catalytic amount of N,N-dimethylaminopyridine followed by 139 mg 2-thiophenesulfonyl chloride and the mixture stirred at room temperature. After 30 minutes, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate, extracted with ethyl acetate and dried over sodium sulfate. Concentration in vacuo gave the crude title compound.

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-d5e28526c5d94172be0820c09092ade0
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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