Sodium Nitrite → (6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl-1H-[1,2,3]triazolo[4,5-c]pyridine

HRID 219073Notes

Reaction equation

HRID 219073 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][C:19]=4[NH2:24])=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:25]([O-])=O.[Na+]>CC(O)=O.O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][N:17]4[C:18]5[CH:23]=[CH:22][N:21]=[CH:20][C:19]=5[N:24]=[N:25]4)=[N:14][N:15]=3)[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 67503473N4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)pyridine-3,4-diamine

Product 1

HCID 57690935(6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl-1H-[1,2,3]triazolo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of N4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)pyridine-3,4-diamine (0.0640 g, 0.202 mmol) in HOAc (5 mL) was added sodium nitrite (0.0153 g, 0.222 mmol) in water (2 mL). Stirred for 1 h. Concentrated. Took up in DMSO and purified on RPHPLC. Took fractions containing product and made basic with 9% sodium carbonate and removed volatiles in vacuo. Product crashed out and was isolated by filtration. MS m/z=329.2[M+1]+. Calc'd for C17H12N8: 328.3.

Workup

  1. concentrationConcentrated
  2. custompurified on RPHPLC
  3. additionTook fractions containing product
  4. customremoved volatiles in vacuo
  5. customwas isolated by filtration

Sources & evidence

ORD record
ord-3aa28874a396461097832a46bd541fe8
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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