Hydrochloric Acid → HCID 23581343, compound

HRID 1828509Notes

Reaction equation

HRID 1828509 reaction equation
[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:37]=[CH:36][N:14]3[C:15](=[O:35])[C:16](/[CH:26]=[CH:27]/[C:28]([O:30]C(C)(C)C)=[O:29])=[C:17]([O:19][CH2:20][CH:21]4[CH2:25][CH2:24][O:23][CH2:22]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].Cl>O1CCOCC1>[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:37]=[CH:36][N:14]3[C:15](=[O:35])[C:16](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[C:17]([O:19][CH2:20][CH:21]4[CH2:25][CH2:24][O:23][CH2:22]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86588140HCID 86588140, compound2×

Product 1

HCID 23581343HCID 23581343, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The tert-butyl (E)-3-{8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (101 mg, 0.193 mmol) obtained in (B) was dissolved in 1,4-dioxane (1.6 ml), added with 4 N hydrochloric acid in 1,4-dioxane (3.2 ml), and then the mixture was stirred at room temperature for 16.25 hours. The reaction solution was concentrated, added with saturated aqueous sodium hydrogencarbonate, neutralized with phosphate buffer (pH 7-8), and then extracted with a mixture of chloroform/methanol (10:1, v/v). The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by thin layer chromatography (chloroform:methanol=20:1, v/v) to obtain the title compound (77.1 mg, 86%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionadded with saturated aqueous sodium hydrogencarbonate
  3. extractionextracted with a mixture of chloroform/methanol (10:1
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-0f8a76dcdb62463aacda32dc9b587eb4
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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