Hydrochloric Acid → HCID 58424886, compound

HRID 2409419Notes

Reaction equation

HRID 2409419 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]2[N:7](CC3C=CC(OC)=CC=3)[C:8](=[O:16])[C:9]3[CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[C:14]=3[C:5]=2[CH:4]=1.[OH-].[Na+].Cl>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]2[NH:7][C:8](=[O:16])[C:9]3[CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[C:14]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58424987HCID 58424987, compound

Product 1

HCID 58424886HCID 58424886, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

The compound (440 mg, 1.20 mmol) prepared in step 1 was dissolved in excess trifluoroacetic acid (3 ml), and the resulting mixture was heated at 100° C. for 18 hours in sealed-tube. The mixture was poured into ice water and acidified with 2 N sodium hydroxide aqueous solution. After neutralizing with 2 N hydrochloric acid aqueous solution, the crude solution was extracted with dichloromethane and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (dichloromethane:methanol=10:1) to obtain the title compound (260 mg, yield: 88%, white solid).

Workup

  1. extractionthe crude solution was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was then purified by flash column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-993ca8873a5f44fc8ae52f4a64f252b7
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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