Hydrazine hydrate (1:1) → HCID 178507269, compound

HRID 1695212Notes

Reaction equation

HRID 1695212 reaction equation
O=[C:2]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=[CH:9]2)[CH2:3][C:4]#[N:5].O.NN.NC1C=C[NH:31][N:30]=1>CCO>[NH:11]1[C:12]2[C:8](=[CH:7][C:6]([C:2]3[CH:3]=[C:4]([NH2:5])[NH:30][N:31]=3)=[CH:14][CH:13]=2)[CH:9]=[CH:10]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67189430HCID 67189430, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 178507269HCID 178507269, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-Oxo-3-(1-triisopropylsilanyl-1H-indol-5-yl)-propionitrile (490 mg, 1.44 mmol) in 15 mL of absolute EtOH, 720 μL of hydrazine monohydrate (14.4 mmol) were added and the reaction refluxed for 18 hours. LC-MS showed complete conversion to the aminopyrazole and also silyl deprotection. The mixture was concentrated under reduced pressure, and purified with SiO2 column (eluent gradient from 100% DCM to DCM:MeOH 9:1) to afford the title compounds (120mg, yield: 41%)

Workup

  1. temperaturethe reaction refluxed for 18 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompurified with SiO2 column (eluent gradient from 100% DCM to DCM:MeOH 9:1)

Sources & evidence

ORD record
ord-71cce52b758a43d1ab5d6e71821e08d0
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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