2-[N-methyl-N-(4-nitrophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one → HCID 23287606, compound

HRID 367187Notes

Reaction equation

HRID 367187 reaction equation
[CH3:1][N:2]([C:12]1[S:13][C:14]2[N:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16](=[O:18])[N:17]=1)[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=[O:10])=[CH:5][CH:4]=1.[H][H]>[Pd].CN(C=O)C>[OH:10][NH:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([C:12]2[S:13][C:14]3[N:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16](=[O:18])[N:17]=2)[CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 232877462-[N-methyl-N-(4-nitrophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 23287606HCID 23287606, compoundYield 6.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.181 g (3.76 mmol) of 2-[N-methyl-N-(4-nitrophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one obtained in Example 63, 100 ml of DMF and 250 mg of 10% Pd on carbon was stirred in an atmosphere of hydrogen for 6 days. The reaction mixture was then heated so that the compound thus precipitated was dissolved. The insoluble matters were hot-removed by filtration. The solution thus obtained was then allowed to cool to room temperature. The resulting crystal was collected by filtration, washed with THF and then with ethanol, and then dried under reduced pressure to obtain 77 mg of 2-[N-(4-hydroxyaminophenyl)-N-methylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. temperatureThe reaction mixture was then heated so that the compound
  2. customthus precipitated
  3. dissolutionwas dissolved
  4. customThe insoluble matters were hot-removed by filtration
  5. customThe solution thus obtained
  6. filtrationThe resulting crystal was collected by filtration
  7. washwashed with THF
  8. dry with materialwith ethanol, and then dried under reduced pressure

Sources & evidence

ORD record
ord-9b1cd0e997d448b58b0067e5c8070d80
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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