1,4-Dioxane → HCID 23077478, compound

HRID 1349511Notes

Reaction equation

HRID 1349511 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[CH:12]O[C:10]=1[C:21]([O:23]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[NH2:31][CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C>C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[CH:12][N:31]2[CH2:32][CH2:33][NH:34][C:21](=[O:23])[C:10]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 187201N-BOC-ethylenediamineHCID 23077540HCID 23077540, compound

Product 1

HCID 23077478HCID 23077478, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-benzyloxy-4-oxo-5-(thiazol-2-yl)-4H-pyran-2-carboxylate (1.47 g) was suspended in ethanol (15 ml)-dioxane (15 ml), and tert-butyl (2-aminoethyl)carbamate (0.816 ml) was added. After stirring at 70° C. for 1.5 hr, the solvent was evaporated and 4N hydrochloric acid/dioxane solution (70 ml) and chloroform (10 ml) were added to the residue. After stirring at room temperature for 2 hr, the reaction mixture was concentration under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution (20 ml) and methanol (50 ml) were added to the residue and the mixture was stirred for 2 hr. The solvent was evaporated and the obtained solid was collected by filtration and washed thoroughly with water to give 9-benzyloxy-7-(thiazol-2-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1.07 g)

Workup

  1. additionwas added
  2. customthe solvent was evaporated
  3. addition4N hydrochloric acid/dioxane solution (70 ml) and chloroform (10 ml) were added to the residue
  4. stirringAfter stirring at room temperature for 2 hr
  5. concentrationconcentration under reduced pressure
  6. additionSaturated aqueous sodium hydrogen carbonate solution (20 ml) and methanol (50 ml) were added to the residue
  7. stirringthe mixture was stirred for 2 hr
  8. customThe solvent was evaporated
  9. filtrationthe obtained solid was collected by filtration
  10. washwashed thoroughly with water

Sources & evidence

ORD record
ord-d22543b773f343baa6fa7cf6a7e972a2
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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