Hydroxyamine hydrochloride → HCID 67385777, compound

HRID 905996Notes

Reaction equation

HRID 905996 reaction equation
C(=[N:14][C:15]1[N:16]=[C:17]2[C:23]([CH3:24])=[CH:22][N:21]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]2=[N:19][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])=O.[Na+].NO.Cl>CO>[CH3:24][C:23]1[C:17]2[C:18](=[N:19][CH:20]=[C:15]([NH2:14])[N:16]=2)[N:21]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:22]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86642310HCID 86642310, compound

Product 1

HCID 67385777HCID 67385777, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzhydrylidene-[7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine (91 mg, 0.206 mmol), NaOAc (41 mg, 0.494 mmol) and NH2OH HCl (26 mg, 0.371 mmol) were dissolved in MeOH (2 mL) and stirred at RT overnight, and partitioned between EtOAc and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (12 g SiO2, hexanes/EtOAc 0-90% EtOAc) to give 41 mg of 7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine as a yellow solid (71% yield).

Workup

  1. custompartitioned between EtOAc and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (12 g SiO2, hexanes/EtOAc 0-90% EtOAc)

Sources & evidence

ORD record
ord-6476849008504fc0b3e7b17f29aed3e6
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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