HCID 69256685, compound → HCID 69256990, compound

HRID 1793338Notes

Reaction equation

HRID 1793338 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8](=[O:11])[NH:7][C:6]1=[O:12].CS(O[CH2:18][C@H:19]1[O:28][C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[O:21][CH2:20]1)(=O)=O>O1CCOCC1>[O:21]1[C:22]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[O:28][C@@H:19]([CH2:18][NH:1][CH2:2][CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][C:8](=[O:11])[NH:7][C:6]2=[O:12])[CH2:20]1

Participants

4

Reactant 2

HCID 69256685HCID 69256685, compoundHCID 131725870HCID 131725870, compound

Product 1

HCID 69256990HCID 69256990, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of intermediate (54) (0.058 mol) in dioxane (400 ml) was stirred. A mixture of intermediate (3) (0.029 mol) and CaO (2.4 g) was added. The reaction mixture was stirred at 140° C. for 16 hours. The solvent was evaporated. DCM and water was added to the residue. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by high-performance liquid chromatography over silica gel (eluent:CH2Cl2/(CH3OH/NH3) 90/10). The product fractions were collected and the solvent was evaporated. The residue was dissolved in ethanol and converted into the ethanedioic acid salt (1:1). The formed precipitate was filtered off and dried, yielding 1.5 g of (S)-1-[3-[[(2,3-dihydro[1,4]dioxino[2,3-b]pyridin-3-yl)methyl]amino]propyl]dihydro-2,4(1H,3H)-pyrimidinedione (compound 25), mp.186; [α]D20 =−37.46°, (c=26.56 mg/5 ml DMF).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 140° C. for 16 hours
  3. customThe solvent was evaporated
  4. additionDCM and water was added to the residue
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by high-performance liquid chromatography over silica gel (eluent:CH2Cl2/(CH3OH/NH3) 90/10)
  9. customThe product fractions were collected
  10. customthe solvent was evaporated
  11. dissolutionThe residue was dissolved in ethanol
  12. filtrationThe formed precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-c60ac8e4ac2c4b1f93c294d3f5c814f1
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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