Benzenesulfonyl chloride → HCID 68677022, compound

HRID 2233046Notes

Reaction equation

HRID 2233046 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]2[N:7]([C:15](=[O:18])[NH:16][N:17]=2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:10]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[C:11]([C:9]1[N:10]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[C:6]2[N:7]([C:15](=[O:18])[NH:16][N:17]=2)[CH:8]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68675419HCID 68675419, compound

Product 1

HCID 68677022HCID 68677022, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 50 mg of 8-(2-amino-ethylamino)-6-tert-butyl-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one, 97 mg of phenylsulfonyl chloride and 61 mg of diisopropylethylamine in DMF (1.0 mL) was stirred at ambient temperature for 16 h. The reaction mixture was diluted with EtOAc and washed with water and then sat. sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to provide the title compound as a white solid. MS (M+H+)=391.4.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f45854e2e2774a92ba1764961de7679e
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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