Hydroxyamine hydrochloride → tert-Butyl 4-(5-bromo-3-((1-(hydroxyamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylate

HRID 1045747Notes

Reaction equation

HRID 1045747 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([N:21]=[C:22]([N:24](C)C)[CH3:23])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Cl.N[OH:29]>CO>[Br:1][C:2]1[N:3]=[C:4]([N:21]=[C:22]([NH:24][OH:29])[CH3:23])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58447046tert-Butyl 4-(5-bromo-3-((1-(dimethylamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 136056833tert-Butyl 4-(5-bromo-3-((1-(hydroxyamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(5-bromo-3-((1-(dimethylamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylate (2.8 g, 6.6 mmol) and methanol (25 mL). To the above solution was added hydroxylamine hydrochloride (0.76 g, 10.9 mmol) in one portion. The mixture was stirred at room temperature for 16 h. Work-up: the solvent was evaporated. The resulting crystalline solid was washed with water and collected by filtration. The solid was washed with ethanol (100 mL) and dried, to afford 2.3 g (84%) of the product as a white solid.

Workup

  1. customthe solvent was evaporated
  2. washThe resulting crystalline solid was washed with water
  3. filtrationcollected by filtration
  4. washThe solid was washed with ethanol (100 mL)
  5. customdried

Sources & evidence

ORD record
ord-a311399fae5c4b629916340eac4a1378
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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