Potassium Hydroxide → HCID 11223639, compound

HRID 1108100Notes

Reaction equation

HRID 1108100 reaction equation
[C:1]([C:3]1([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([S:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[CH:26][N:25]=[C:24]4[CH3:28])=[CH:19][CH:18]=3)[CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].[OH-:29].[K+]>C(O)(C)(C)C>[F:15][C:13]1[CH:12]=[C:11]([S:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[CH:26][N:25]=[C:24]3[CH3:28])=[CH:19][CH:18]=2)[CH:10]=[C:9]([C:3]2([C:1]([NH2:2])=[O:29])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:14]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11269401HCID 11269401, compound

Product 1

HCID 11223639HCID 11223639, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-cyano-4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran (Example 25, 1.71 g, 4.36 mmol) in tert-butanol (20 ml) was added powdered potassium hydroxide (85%, 860 mg, 13 mmol). The resulting mixture was heated at reflux temperature for 4 h, cooled and concentrated in vacuo . Water (50 ml) was added and the precipitates were collected by filtration and washed with 50 ml of ethyl acetate. After drying in vacuo, 560 mg (31%) of the titled compound was obtained as a yellow powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature for 4 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additionWater (50 ml) was added
  6. filtrationthe precipitates were collected by filtration
  7. washwashed with 50 ml of ethyl acetate
  8. customAfter drying in vacuo

Sources & evidence

ORD record
ord-e4365b3b855e4b55a8557b82bfefc4a3
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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