Hydroxylamine → HCID 178513432, compound

HRID 1674996Notes

Reaction equation

HRID 1674996 reaction equation
[NH2:1][OH:2].[F:3][C:4]([F:23])([F:22])[C:5]1[N:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]#[N:21])[CH2:16][CH2:15]3)[CH:12]=[CH:13][C:8]2=[N:7][N:6]=1>C(O)C>[OH:2][NH:1][C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[CH:13][C:8]3[N:9]([C:5]([C:4]([F:23])([F:3])[F:22])=[N:6][N:7]=3)[N:10]=2)[CH2:15][CH2:16]1)=[NH:21]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 866380754-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazine-1-carbonitrile

Product 1

HCID 178513432HCID 178513432, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine (50% w/v aqueous solution) (0.667 mL, 10.09 mmol) was added to a stirred suspension of 4-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazine-1-carbonitrile (2.5 g, 8.41 mmol) in ethanol (16.82 mL) and the suspension was stirred at ambient temperature. Over 20 minutes the starting material largely dissolved and the product began to crystallise. The mixture was stirred for 2 hours and the precipitate was collected by filtration, washed with EtOH followed by ether and dried under vacuum to afford N-hydroxy-4-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazine-1-carboximidamide (2.410 g, 87%) as a colourless crystalline solid.

Workup

  1. dissolutionOver 20 minutes the starting material largely dissolved
  2. customto crystallise
  3. stirringThe mixture was stirred for 2 hours
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with EtOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7b16bedb43ed428e89c34a464e59f739
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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