Sodium Hydroxide → HCID 59740991, compound

HRID 2192175Notes

Reaction equation

HRID 2192175 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)C)=[CH:15][C:14]=2[F:23])[N:5](S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=1)#[N:2].[OH-].[Na+]>C(O)C.C1COCC1>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]3[NH:5][CH:4]=[C:3]([C:1]#[N:2])[C:11]=23)=[C:14]([F:23])[CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59740997HCID 59740997, compound

Product 1

HCID 59740991HCID 59740991, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

30 mg (0.065 mmol) of N-[4-({3-cyano-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide are dissolved in a mixture of 3 ml of ethanol and 3 ml of THF. 1.5 ml of 20% strength aqueous sodium hydroxide solution are added, and the mixture is heated at 90° C. overnight. Another 1 ml of 20% strength-aqueous sodium hydroxide solution is then added, and a further ml after 6 hours. The mixture is again stirred overnight. The reaction mixture is then partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure. The crude product is reacted without further purification.

Workup

  1. waitThe mixture is again stirred overnight
  2. customThe reaction mixture is then partitioned between ethyl acetate and water
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-e0e82844bfac4672906414e65d1b7cce
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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