Sulfuric Acid → HCID 23057945, compound

HRID 346507Notes

Reaction equation

HRID 346507 reaction equation
S(=O)(=O)(O)O.[N:6]1([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[N:22]=[C:23](N)[S:24][CH:25]=4)=[N:19][N:20]=3)[N:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[Br-:27].[Na+].N([O-])=O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2].CC(O)C.C(Cl)(Cl)Cl>[Br:27][C:23]1[S:24][CH:25]=[C:21]([C:18]2[N:16]3[N:17]=[C:12]([N:6]4[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]4)[CH:13]=[CH:14][C:15]3=[N:20][N:19]=2)[N:22]=1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 253881Sodium BromideHCID 230579504-[6-(Piperidin-1-yl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]-1,3-thiazol-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 23057945HCID 23057945, compoundYield 6.9%

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent3×HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-5 °C

Procedure

A solution mixture of concentrated sulfuric acid (1.5 ml) and water (3 ml) was cooled to −5° C., and 4-(6-piperidin-1-yl-1,2,4-triazolo[4,3-b]pyridazin-3-yl)-1,3-thiazol-2-amine (0.90 g), copper (II) sulfate (1.50 g) and sodium bromide (0.62 g) were added successively, and the mixture was stirred at 0° C. for 5 minutes. Then, a solution of sodium nitrite (0.25 g) in water (1.6 ml), followed by stirring at room temperature overnight. The reaction solution was combined with water, chloroform and 2-propanol, and insoluble materials were filtered off. The resultant organic phase was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1) to obtain crude crystals, which were then recrystallized from ethanol-diethyl ether to obtain 3-(2-bromo-1,3-thiazol-4-yl)-6-piperidin-1-yl-1,2,4-triazolo[4,3-b]pyridazine (75 mg) as pale yellow crystals.

Workup

  1. stirringby stirring at room temperature overnight
  2. filtrationwere filtered off
  3. washThe resultant organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1)
  7. customto obtain crude crystals, which
  8. customwere then recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-d4b42c9368c848eda00c76dc5d153552
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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