Trifluoroacetic acid → HCID 67340789, compound

HRID 1674993Notes

Reaction equation

HRID 1674993 reaction equation
[C:1](O)([C:3]([F:6])([F:5])[F:4])=O.[NH:8]([C:10]1[N:15]=[N:14][C:13]([C:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH:17]=2)=[CH:12][CH:11]=1)[NH2:9]>>[NH:19]1[CH2:18][CH:17]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]3[N:15]([C:1]([C:3]([F:6])([F:5])[F:4])=[N:9][N:8]=3)[N:14]=2)[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67339970HCID 67339970, compound

Product 1

HCID 67340789HCID 67340789, compoundYield 20.29%

Conditions

Temperature
70 °C

Procedure

TFA (2 mL) was added in one portion to tert-butyl 4-(6-hydrazinylpyridazin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (480 mg, 1.65 mmol) which dissolved with a vigorous effervescence. The solution was stirred for 24 hours at 70° C. The solution was evaporated and the residue was dissolved in methanol. It was run on an SCX cartridge, eluting with 2M ammonia in methanol. Product containing fractions were evaporated to dryness and triturated with ether to afford 6-(1,2,3,6-tetrahydropyridin-4-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (90 mg, 20.29%) as a cream solid.

Workup

  1. dissolutiondissolved with a vigorous effervescence
  2. customThe solution was evaporated
  3. dissolutionthe residue was dissolved in methanol
  4. washeluting with 2M ammonia in methanol
  5. additionProduct containing fractions
  6. customwere evaporated to dryness
  7. customtriturated with ether

Sources & evidence

ORD record
ord-d8989c316fe8410cbc0d53ea7d4d04d9
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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