Hydroxyamine hydrochloride → HCID 136391022, compound

HRID 2369007Notes

Reaction equation

HRID 2369007 reaction equation
[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17](=O)[CH3:18])[CH:9]=1.Cl.[NH2:31][OH:32]>CCO.N1C=CC=CC=1>[CH3:29][Si:2]([CH3:28])([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17](=[N:31][OH:32])[CH3:18])[CH:9]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66584720HCID 66584720, compound

Product 1

HCID 136391022HCID 136391022, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

A solution of 1-[7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)pyrazolo[1,5-a]pyrimidin-5-yl]ethanone (4.34 g, 9.94 mmol) in 1:1 EtOH/pyridine (50 mL) was treated with hydroxylamine hydrochloride (3.45 g, 49.7 mmol). The resulting mixture was stirred at room temperature for 1.5 h and then concentrated under reduced pressure to remove most solvent. The residue was partitioned between EtOAc (100 mL) and water (60 mL), the layers were separated, and the organic phase was washed with water (60 mL) and brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure to give the title compound, 1-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)ethanone oxime (4.90 g, 85% purity, 93% yield) as an off-white semisolid: MS (ESI+) for C20H37N5O3Si2 m/z 452 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove most solvent
  3. customThe residue was partitioned between EtOAc (100 mL) and water (60 mL)
  4. customthe layers were separated
  5. washthe organic phase was washed with water (60 mL) and brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d56d1f2abcde42c1a505916187a36f46
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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