Hydroxyamine hydrochloride → (S)-tert-Butyl 4-(5-Aminopyrazin-2-yl)-3-methylpiperazine-1-carboxylate

HRID 1022000Notes

Reaction equation

HRID 1022000 reaction equation
C1(C(=[N:14][C:15]2[N:16]=[CH:17][C:18]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C@@H:22]3[CH3:34])=[N:19][CH:20]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>CO>[NH2:14][C:15]1[N:16]=[CH:17][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C@@H:22]2[CH3:34])=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86684427(S)-tert-Butyl 4-(5-(Diphenylmethyleneamino)pyrazin-2-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 86684428(S)-tert-Butyl 4-(5-Aminopyrazin-2-yl)-3-methylpiperazine-1-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 230b (3.3 g, 7.2 mmol) in methanol (25 mL) were added sodium acetate (708 mg, 8.6 mmol) and hydroxylamine hydrochloride (907 mg, 8.6 mmol). The reaction mixture was stirred for 0.5 h. It was then concentrated in vacuo. The residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (50:1 to 30:1) to afford 230c as yellow oil (1.35 g, 64%). MS: [M+H]+ 294.3.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was purified by silica-gel column chromatography
  3. washeluting with dichloromethane/methanol (50:1 to 30:1)

Sources & evidence

ORD record
ord-a600b44577a04df7a9012b0ab4f7c4ca
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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