Water → HCID 58087281, compound

HRID 1964979Notes

Reaction equation

HRID 1964979 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[CH:18]=2)[NH:13][CH:12]=1)=O.O.NN.[OH-].[K+].O>C(O)COCCO>[F:1][C:2]1[C:3]([CH2:9][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)[CH:18]=3)[NH:13][CH:12]=2)=[CH:4][CH:5]=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 57595739HCID 57595739, compound

Product 1

HCID 58087281HCID 58087281, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

To (2-fluoro-3-hydroxy-phenyl)-(5-thiophen-2-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (P-0521, 50.0 mg, 0.15 mmol) in diethylene glycol (5.0 mL) were added hydrazine hydrate (1.0 mL, 0.020 mol) and potassium hydroxide (200.0 mg, 3.56 mmol). The reaction mixture was heated in a CEM Discovery microwave instrument at 180° C. for 20 minutes, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The desired compound was isolated by silica gel column chromatography eluting with 5% methanol in methylene chloride to give a white solid (P-0052, 10 mg, 20%). MS(ESI) [M+H+]−=325.2.

Workup

  1. temperatureThe reaction mixture was heated in a CEM Discovery
  2. customat 180° C.
  3. customfor 20 minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6dadcadda66b412daa6af74b7df8f9e2
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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