Hydrochloric Acid → 2-[5-Amino-1-(3-hydroxy-phenyl)-1H-pyrazol-3-yl]-2-methyl-propionitrile

HRID 2200049Notes

Reaction equation

HRID 2200049 reaction equation
[CH3:1][C:2]([CH3:10])([C:5](=O)[CH2:6][C:7]#[N:8])[C:3]#[N:4].[NH:11]([C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1)[NH2:12].Cl>CCO>[NH2:8][C:7]1[N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[N:12]=[C:5]([C:2]([CH3:10])([CH3:1])[C:3]#[N:4])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 143447513-HydrazinylphenolHCID 866201652,2-Dimethyl-3-oxopentanedinitrile

Product 1

HCID 1177292592-[5-Amino-1-(3-hydroxy-phenyl)-1H-pyrazol-3-yl]-2-methyl-propionitrileYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,2-Dimethyl-3-oxo-pentanedinitrile (WO 2008/034008, which is incorporated herein by reference in its entirety, 353 mg, 2.80 mmol) and Intermediate 20a (387 mg, 2.80 mmol) were suspended in EtOH (10 mL) and concentrated HCl was added (711 μL, 8.53 mmol) and the reaction was refluxed for 90 min. The reaction was cooled, concentrated in vacuo and partitioned between H2O and EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo and the resulting oil was triturated with pentane/Et2O (9:1) to afford the title compound as a brown solid (363 mg, 53%). LCMS (Method 3): Rt 2.77 min, m/z 243.3 [MH+].

Workup

  1. temperaturethe reaction was refluxed for 90 min
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. custompartitioned between H2O and EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customthe resulting oil was triturated with pentane/Et2O (9:1)

Sources & evidence

ORD record
ord-1474e64286f146ee9f0e9be377e19acd
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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