Hydrazine hydrate (1:1) → HCID 136352998, compound

HRID 336863Notes

Reaction equation

HRID 336863 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[O:17][C:16]([C:18]2[C:23]([C:24]#[N:25])=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[N:21]=[C:20]3[NH:33][N:34]=[CH:35][C:19]=23)=[CH:15][CH:14]=1.O.NN>C(O)C>[NH2:3][CH2:12][C:13]1[O:17][C:16]([C:18]2[C:23]([C:24]#[N:25])=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[N:21]=[C:20]3[NH:33][N:34]=[CH:35][C:19]=23)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 136414065HCID 136414065, compound

Product 1

HCID 136352998HCID 136352998, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 0.39 g (0.80 mmol) of 4-(5-((1,3-dioxoisoindoline-2-yl)methyl)furan-2-yl)-6-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile obtained following the sequences of procedures B7 and D1, in 8 ml of ethanol, are added 368 μL (0.38 g, 7.6 mmol) of hydrazine hydrate. The mixture is refluxed for 3 h. The precipitate obtained is filtered and dissolved in water. The mixture is brought to pH=7-8 with 30% sodium hydroxide and extracted with ethyl acetate. The organic phases are dried over magnesium sulfate, filtered, and concentrated. The residue obtained is purified by silica chromatography (eluent 7N NH4OH in methanol in dichloromethane: 10:90) to yield 0.057 g (22%) of 4-(5-(aminomethyl)furan-2-yl)-6-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a yellow solid.

Workup

  1. customobtained
  2. temperatureThe mixture is refluxed for 3 h
  3. customThe precipitate obtained
  4. filtrationis filtered
  5. dissolutiondissolved in water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phases are dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue obtained
  11. customis purified by silica chromatography (eluent 7N NH4OH in methanol in dichloromethane: 10:90)

Sources & evidence

ORD record
ord-a4d845f85622404e9c4d0a1a7fbea888
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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