Benzenesulfonyl chloride, 3,4-dichloro- → HCID 69767155, compound

HRID 1071975Notes

Reaction equation

HRID 1071975 reaction equation
[N:1]([CH2:4][C@H:5]1[NH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15])=[N+]=[N-].[Cl:16][C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[Cl:23].[H][H]>N1C=CC=CC=1.CCO.[Pd]>[NH2:1][CH2:4][C@H:5]1[N:14]([S:24]([C:19]2[CH:20]=[CH:21][C:22]([Cl:23])=[C:17]([Cl:16])[CH:18]=2)(=[O:26])=[O:25])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15]

Participants

7

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 86593352HCID 86593352, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69767155HCID 69767155, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of (3R)-3-(azidomethyl)-3,4-dihydroquinoxalin-2(1H)-one (122 mg, 0.60 mmol) in pyridine (3 mL) was added 3,4-dichlorobenzenesulfonyl chloride (300 uL, 1.92 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure and purified using silica gel chromatography eluting with CH2Cl2-3% MeOH in CH2Cl2. The resulting product (137 mg, 0.33 mmol) was dissolved in EtOH (3 mL) and Pd/C (93 mg, 0.087 mmol) was added. A hydrogen balloon was placed over the reaction mixture for 5.5 hours before it was filtered through celite and concentrated to give (3R)-3-(aminomethyl)-4-[(3,4-dichlorophenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one, which was used without further purification. LCMS (ES) 385.9.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified
  3. washeluting with CH2Cl2-3% MeOH in CH2Cl2
  4. filtrationwas filtered through celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb5d8a2ac5d44303ad3559bae3ef7090
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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