Hydrochloric Acid → HCID 67210973, compound

HRID 452145Notes

Reaction equation

HRID 452145 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:25]=[CH:24][C:11]3/[C:12](=C/C#N)/[C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[CH2:15][CH2:16][C:10]=3[CH:9]=2)[C:5]2[CH:26]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=[C:29]([CH3:30])[C:4]=2[N:3]=1.[OH-:37].[Na+].Cl.[CH2:40]([OH:42])[CH3:41]>>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:25]=[CH:24][C:11]3/[C:12](=[CH:41]/[C:40]([OH:37])=[O:42])/[C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[CH2:15][CH2:16][C:10]=3[CH:9]=2)[C:5]2[CH:26]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=[C:29]([CH3:30])[C:4]=2[N:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 67211490HCID 67211490, compound

Product 1

HCID 67210973HCID 67210973, compoundYield 41%

Procedure

Compound 53 (80 mg, 0.17 mmol) obtained in Example 53 was suspended in ethanol (2 mL), 10 mol/L aqueous sodium hydroxide solution (3.1 mL) was added, and the mixture was stirred under reflux for 3 days. Under ice-cooling, the mixture was adjusted to pH 1 with 2 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=98/2 to 90/10) to give the title compound (compound 55) (34 mg, 41%).

Workup

  1. temperatureunder reflux for 3 days
  2. temperatureUnder ice-cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=98/2 to 90/10)

Sources & evidence

ORD record
ord-6d3c151b1a2d4ca9af99c8972611c1e8
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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