Hydroxyamine hydrochloride → HCID 67385653, compound

HRID 906002Notes

Reaction equation

HRID 906002 reaction equation
C(=[N:14][C:15]1[N:16]=[C:17]2[C:23]([Cl: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>[Cl: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]([CH3:32])([CH3:31])[CH3:30])[CH:22]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86642312HCID 86642312, compound

Product 1

HCID 67385653HCID 67385653, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzhydrylidene-[7-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine (992 mg, 2.14 mmol), NaOAc (421 mg, 5.14 mmol) and NH2OH HCl (268 mg, 3.85 mmol) were dissolved in MeOH (21 mL) and stirred at RT overnight, and partitioned between EtOAc and H2O. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (150 g SiO2, hexanes/EtOAc 0 to 50% EtOAc) to give 202 mg of 7-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine as a white solid (32% yield).

Workup

  1. custompartitioned between EtOAc and H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (150 g SiO2, hexanes/EtOAc 0 to 50% EtOAc)

Sources & evidence

ORD record
ord-8c0ab6773f694a44a67ff57596184b41
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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