Potassium Hydroxide → HCID 68195236, compound

HRID 2370653Notes

Reaction equation

HRID 2370653 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=3)=[N:19][C:12]=2[N:11]2[CH:31]=[CH:32][N:33]=[C:10]12.[OH-].[K+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[N:17][C:18]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)=[N:19][C:12]=2[N:11]2[CH:31]=[CH:32][N:33]=[C:10]12

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68194894HCID 68194894, compound

Product 1

HCID 68195236HCID 68195236, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of Example 216 (0.6 g, 1.24 mmol) in 10 mL methanol and 3 mL water was added KOH (0.28 g, 4.99 mmol). The reaction was heated at 50 degrees overnight and at 60 degrees for 1.5 hours. The reaction mixture was cooled and concentrated. The crude material was suspended in ethyl acetate, acidified with 1M aqueous HCl, and the aqueous layer was extracted with dichloromethane (2×). The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated. The material in the aqueous layer was filtered and the solid was dried to provide the title compound. MS (ESI+) m/z 467.2 (M+H)+.

Workup

  1. temperatureThe reaction was heated at 50 degrees overnight and at 60 degrees for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×)
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe material in the aqueous layer was filtered
  10. customthe solid was dried

Sources & evidence

ORD record
ord-47ec8f14c33f4142bd78029bbeec3af2
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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