Potassium Hydroxide → HCID 25190386, compound

HRID 219765Notes

Reaction equation

HRID 219765 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[C:8]2[C:4]=1[C:5]([NH:22][C:23](=[O:33])[CH2:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH3:32])[CH2:27][CH2:26]1)([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:6](=[O:14])[NH:7]2.[OH-:36].[K+]>CC(O)(C)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:5]2([NH:22][C:23](=[O:33])[CH2:24][N:25]3[CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH2:30]3)[C:4]3[C:8](=[CH:9][C:10]([C:12]([NH2:13])=[O:36])=[CH:11][C:3]=3[C:2]([F:1])([F:34])[F:35])[NH:7][C:6]2=[O:14])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66602253HCID 66602253, compound

Product 1

HCID 25190386HCID 25190386, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

0.16 g of the product obtained in Example 4, 0.47 g of potassium hydroxide and 7 ml of t-BuOH are placed in a round-bottomed flask equipped with a magnetic stirrer. The mixture is left to react at 50° C. for 5 hours. The resulting mixture is filtered through Celite and washed with THF. The filtrate is evaporated under vacuum and the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. 100 mg of an oil are obtained, which oil is purified by flash chromatography, eluting with 8/2 ethyl acetate/methanol. 10 mg of white solid are isolated.

Workup

  1. customequipped with a magnetic stirrer
  2. waitThe mixture is left
  3. customto react at 50° C. for 5 hours
  4. filtrationThe resulting mixture is filtered through Celite
  5. washwashed with THF
  6. customThe filtrate is evaporated under vacuum
  7. washwashed with water
  8. dry with materialThe organic phase is dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-a5f34ff25a584c5ba21faf4efbd1e5d1
Source dataset
uspto-grants-2012_06
Patent number
US08202871B2

Reaction notes

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