Water → HCID 53858786, compound

HRID 1458575Notes

Reaction equation

HRID 1458575 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 72 h, 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 the title compound (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-acdf6deae49f49a8a190b0127f400e5e
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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