Sodium Hydroxide → HCID 22063599, compound

HRID 1828420Notes

Reaction equation

HRID 1828420 reaction equation
[CH:1]1([C:5]2[N:6]=[C:7]([CH2:10][CH2:11][C:12]3[CH:36]=[CH:35][N:15]4[C:16](=[O:34])[C:17](/[CH:26]=[C:27](\[CH3:33])/[C:28]([O:30]CC)=[O:29])=[C:18]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[N:19]=[C:14]4[CH:13]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:5]2[N:6]=[C:7]([CH2:10][CH2:11][C:12]3[CH:36]=[CH:35][N:15]4[C:16](=[O:34])[C:17](/[CH:26]=[C:27](\[CH3:33])/[C:28]([OH:30])=[O:29])=[C:18]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[N:19]=[C:14]4[CH:13]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 86588095HCID 86588095, compound

Product 1

HCID 22063599HCID 22063599, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (E)-3-{8-[2-(4-cyclobutyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-methyl-2-propenoate (120 mg, 0.236 mmol) dissolved in methanol (5 ml) was added dropwise with 1 N aqueous sodium hydroxide (2 ml) under ice cooling. The reaction solution was stirred for 10 minutes and then warmed to room temperature because the reaction did not progress. The reaction solution was stirred for 45 minutes, then further added with 1 N aqueous sodium hydroxide (2 ml), and after 1 hour, further added with 1 N aqueous sodium hydroxide (2 ml). The solvent was evaporated under reduced pressure, and the resulting sodium salt of the title compound was dissolved in 1,4-dioxane, added with 4 N hydrochloric acid (6 ml) and stirred. Then the reaction solution was concentrated under reduced pressure, and the residue was neutralized with saturated aqueous sodium hydrogencarbonate and extracted with chloroform and methanol. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=30:1) to obtain 75 mg (66%) of the title compound as yellow crystals.

Workup

  1. stirringThe reaction solution was stirred for 45 minutes
  2. waitafter 1 hour
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe resulting sodium salt of the title compound was dissolved in 1,4-dioxane
  5. additionadded with 4 N hydrochloric acid (6 ml)
  6. stirringstirred
  7. concentrationThen the reaction solution was concentrated under reduced pressure
  8. extractionextracted with chloroform and methanol
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-05df43f2847a4ee4899c63b307473161
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…