Water → HCID 53906871, compound

HRID 343801Notes

Reaction equation

HRID 343801 reaction equation
N1C=CC=CC=1.[CH3:7][S:8]([O:11]S(C)(=O)=O)(=O)=[O:9].[NH2:16][C:17]1[C:26]([CH3:27])=[C:25]([Cl:28])[CH:24]=[C:23]2[C:18]=1[N:19]=[C:20]([O:31][CH3:32])[C:21]([O:29][CH3:30])=[N:22]2.O>O1CCCC1.C(OCC)(=O)C>[Cl:28][C:25]1[CH:24]=[C:23]2[C:18]([N:19]=[C:20]([O:31][CH3:32])[C:21]([O:29][CH3:30])=[N:22]2)=[C:17]([NH:16][S:8]([CH3:7])(=[O:11])=[O:9])[C:26]=1[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 81560Methanesulfonic anhydrideHCID 22614884HCID 22614884, compound

Product 1

HCID 53906871HCID 53906871, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (80 μl, 78 mg, 0.985 mmol) and methanesulphonic anhydride (172 mg, 0.985 mmol) were added to a solution of 5-amino-7-chloro-2,3-dimethoxy-6-methylquinoxaline (50 mg, 0.197 mmol) in dry tetrahydrofuran (1.6 ml) at room temperature under nitrogen. After stirring for 17 hours water (0.3 ml) was added and stirring continued for 1 hour. The mixture was diluted with ethyl acetate (15 ml) and washed with 2M hydrochloric acid (5 ml), water(5 ml), saturated sodium bicarbonate solution (5 ml) and brine (5 ml) and then dried (MgSO4), filtered and concentrated under reduced pressure to afford N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulphonamide (66 mg, 100%) as a white solid mp 228°-229° C.

Workup

  1. additionwas added
  2. washwashed with 2M hydrochloric acid (5 ml), water(5 ml), saturated sodium bicarbonate solution (5 ml) and brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3e33f37085c4a98bc35699897b6baf4
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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