HCID 23287727, compound → HCID 23287731, compound

HRID 367203Notes

Reaction equation

HRID 367203 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]3[N:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[N:13]=2)[CH2:4][CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[S:9][C:10]3[N:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[N:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 23287727HCID 23287727, compound2×HCID 178418287HCID 178418287, compound

Product 1

HCID 23287731HCID 23287731, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

120 mg of 2-(4-hydroxypiperidino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one (compound of Example 108), 250 mg of crushed molecular sieve (3A) and 7.2 ml of methylene chloride were mixed. To the mixture was then added 196 mg of pyridinium chlorochromate (PCC). The mixture was then stirred at room temperature for 1.5 hours. The reaction mixture was immediately filtered through 10 g of a silica gel layer, and then eluted with a 50:1:0.1 mixture of chloroform, methanol and aqueous ammonia. The resulting filtrate and elute were concentrated, subjected to separation through silica gel column chromatography (eluant: 50:1:0.1 mixture of chloroform, methanol and aqueous ammonia), and then washed with hot acetonitrile to obtain 72 mg of 2-(4-oxo-1-piperidinyl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. filtrationThe reaction mixture was immediately filtered through 10 g of a silica gel layer
  2. washeluted with a 50:1:0.1 mixture of chloroform, methanol and aqueous ammonia
  3. washThe resulting filtrate and elute
  4. concentrationwere concentrated
  5. customsubjected to separation through silica gel column chromatography (eluant: 50:1:0.1 mixture of chloroform, methanol and aqueous ammonia)
  6. washwashed with hot acetonitrile

Sources & evidence

ORD record
ord-055052b94ed349119113619a5b8d9c7f
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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