Water → HCID 86588150, compound

HRID 1828547Notes

Reaction equation

HRID 1828547 reaction equation
[F:1][C:2]1[C:3]([CH2:30][CH2:31][C:32]2[S:33][CH:34]=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=2)=[CH:4][C:5]2[N:6]([CH:29]=1)[C:7](=[O:28])[C:8](/[CH:19]=[CH:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13](C=O)[CH2:12]1)[N:10]=2.C[O-:41].[Na+].O>CO>[F:1][C:2]1[C:3]([CH2:30][CH2:31][C:32]2[S:33][CH:34]=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=2)=[CH:4][C:5]2[N:6]([CH:29]=1)[C:7](=[O:28])[C:8](/[CH:19]=[CH:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:41])[CH2:12]1)[N:10]=2

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86588151HCID 86588151, compound2×

Product 1

HCID 86588150HCID 86588150, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tert-butyl (E)-3-{7-fluoro-2-(3-formylpiperidino)-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (147 mg, 0.258 mmol) obtained in (L) was dissolved in methanol (3ml), added with sodium methoxide (33.6 mg, 0.618 mmol), and then stirred at room temperature for 9 hours. The reaction mixture was added with distilled water and extracted with chloroform (twice). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by preparative TLC (chloroform:methanol=100:5) to obtain the title compound (91.6 mg, 65%).

Workup

  1. extractionextracted with chloroform (twice)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe resulting residue was purified by preparative TLC (chloroform:methanol=100:5)

Sources & evidence

ORD record
ord-7728820f0fb548f19e2c9e3e18398ca1
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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