Hydrochloric Acid → 3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-propan-1-ol

HRID 572115Notes

Reaction equation

HRID 572115 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.Cl.[NH:12]([CH2:14][CH2:15][CH2:16][OH:17])[NH2:13].Cl>C(O)C>[NH2:6][C:5]1[N:12]([CH2:14][CH2:15][CH2:16][OH:17])[N:13]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 509884343-Hydrazinylpropan-1-ol dihydrochloride

Product 1

HCID 866867313-(5-Amino-3-tert-butyl-pyrazol-1-yl)-propan-1-olYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4-dimethyl-3-oxo-pentanenitrile (0.7 g, 5.58 mmol) in ethanol (IMS grade, 5 mL) was treated with 3-hydrazino-propan-1-ol dihydrochloride (1 g, 6.13 mmol), followed by conc. HCl (0.05 mL), and the reaction mixture was heated at reflux for 18 h. The mixture was concentrated in vacuo and the residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM to afford the title compound as a white gummy solid (0.94 g, 85%). LCMS (Method 3): Rt 0.42 min, m/z 198 [MH+].

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-180bbe1933cb45b2ba248db74374a3b5
Source dataset
uspto-grants-2015_05
Patent number
US09029373B2

Reaction notes

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