Water → HCID 44608544, compound

HRID 1943687

Reaction equation

HRID 1943687 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[CH3:11][O:12][C:13]1[CH:17]=[C:16]([C:18](Cl)=[O:19])[O:15][N:14]=1.C(N(CC)CC)C.O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:18]([C:16]2[O:15][N:14]=[C:13]([O:12][CH3:11])[CH:17]=2)=[O:19])[C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 121963593-Methoxy-5-isoxazolecarbonyl chlorideHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 44608544HCID 44608544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (100 mg, 0.73 mmol) and 3-methoxy-isoxazol-5-carbonyl chloride (131 mg, 0.80 mmol) were dissolved in dichloromethane. Triethylamine (0.51 ml, 3.65 mmol) was added thereto and then stirred at room temperature for 2 hours. After completion of the reaction by adding water dropwise, the reaction mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=30:1. The fractions containing the product were collected and evaporated to obtain the target compound 43, i.e., (2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-methoxy-isoxazol-5-yl)-methanone, as pale-brown solid (149 mg, 78%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-bf094ab021954322a9bee2d356e54902
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Linked notes

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