Water → HCID 53858786, compound

HRID 343812Notes

Reaction equation

HRID 343812 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[NH2:10][C:11]1[C:20]([Cl:21])=[C:19]([CH2:22][CH3:23])[CH:18]=[C:17]2[C:12]=1[N:13]=[C:14]([O:26][CH3:27])[C:15]([O:24][CH3:25])=[N:16]2.N1C=CC=CC=1.O>O1CCCC1.C(OCC)(=O)C>[Cl:21][C:20]1[C:11]([NH:10][S:2]([CH3:1])(=[O:5])=[O:3])=[C:12]2[C:17](=[CH:18][C:19]=1[CH2:22][CH3:23])[N:16]=[C:15]([O:24][CH3:25])[C:14]([O:26][CH3:27])=[N:13]2

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 81560Methanesulfonic anhydrideHCID 53999444HCID 53999444, compound

Product 1

HCID 53858786HCID 53858786, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulphonic anhydride (671 mg, 3.85 mmol) was added to a stirred solution of 5-amino-6-chloro-7-ethyl-2,3-dimethoxyquinoxaline (207 mg, 0.77 mmol) and anhydrous pyridine (305 mg, 3.85 mmol) in anhydrous tetrahydrofuran (7.7 ml) at room temperature. After 72h, water (3 ml) was added and the mixture was stirred for a further 60 minutes. The mixture was diluted with ethyl acetate and washed with 2M hydrochloric acid (50 ml), water (50 ml), saturated aqueous sodium bicarbonate (50 ml) and saturated aqueous sodium chloride (50 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give N-(6-chloro-7-ethyl-2,3-dimethoxyquinoxalin-5-yl)methanesulphonamide (206 mg, 77%).

Workup

  1. washwashed with 2M hydrochloric acid (50 ml), water (50 ml), saturated aqueous sodium bicarbonate (50 ml) and saturated aqueous sodium chloride (50 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-442e25031de044f39ba350ae99bb1103
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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