Hydrochloric Acid → HCID 86753465, compound

HRID 1458586Notes

Reaction equation

HRID 1458586 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[N:10]1C=CC=CC=1.N[C:17]1[C:26]([F: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.[OH-].[Na+].Cl>ClCCl.C1COCC1>[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]([CH2:1][S:2]([NH2:10])(=[O:5])=[O:3])[C:26]=1[F:27]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 14798Sodium Hydroxide2×HCID 81560Methanesulfonic anhydrideHCID 22096998HCID 22096998, compound

Product 1

HCID 86753465HCID 86753465, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanesulphonic anhydride (0.55 g, 3.16 mmol) and pyridine (255 μl, 3.15 mmol) were added to a stirred suspension of 5-amino-7-chloro-6-fluoro-2,3-dimethoxyquinoxaline (see Preparation 24) (0.274 g, 1.06 mmol) in dichloromethane (15 ml) at room temperature under nitrogen. The mixture was stirred at room temperature overnight, concentrated to dryness and suspended in tetrahydrofuran (30 ml). The reaction mixture was treated with 1M sodium hydroxide (5.3 ml, 5.3 mmol) with ice-cooling, followed by stirring at 5° C. for 1.5 h. The reaction mixture was acidified to pH2 with 2M hydrochloric acid, concentrated and partitioned between water and dichloromethane. The layers were separated and the aqueous layer was extracted with dichloromethane twice. The combined organics were dried (MgSO4) and concentrated to give a pale yellow solid. Suspension in THF (30 ml) and treatment with 1M sodium hydroxide (5.3 ml, 5.3 mmol) at 5° C. was followed by stirring at room temperature for 2 h. The reaction mixture was acidified to pH2 with 2M hydrochloric acid, concentrated to a small volume, diluted with water and filtered. The filtrate was washed with water and cold diethyl ether to afford a white solid (0.32 g, 90%), m.p. 227°-228° C.

Workup

  1. concentrationconcentrated to dryness
  2. temperaturecooling
  3. stirringby stirring at 5° C. for 1.5 h
  4. concentrationconcentrated
  5. custompartitioned between water and dichloromethane
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with dichloromethane twice
  8. dry with materialThe combined organics were dried (MgSO4)
  9. concentrationconcentrated
  10. customto give a pale yellow solid
  11. customat 5° C.
  12. stirringby stirring at room temperature for 2 h
  13. concentrationconcentrated to a small volume
  14. additiondiluted with water
  15. filtrationfiltered
  16. washThe filtrate was washed with water and cold diethyl ether

Sources & evidence

ORD record
ord-bc2f2419f65e428f9d32f7b62d77c727
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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