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

HRID 75625Notes

Reaction equation

HRID 75625 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 cone. 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. temperatureat reflux for 18 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-98787d0f6a47411b9a18f0a0e6f2a14c
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

Loading…