Acetic Anhydride → N-(3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-yl)acetamide

HRID 633499Notes

Reaction equation

HRID 633499 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[N:13]2[N:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:12]2=[N:11][N:10]=1>N1C=CC=CC=1>[Cl:8][C:9]1[N:13]2[N:14]=[C:15]([NH:18][C:5](=[O:7])[CH3:6])[CH:16]=[CH:17][C:12]2=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 67524192HCID 67524192, compound

Product 1

HCID 67524510N-(3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-yl)acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.11 cm3 of acetic anhydride is added to a mixture of 202 mg of 3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-amine in 5 cm3 of pyridine at 0° C. The temperature is allowed to rise to 20° C. over 6 h, then 0.05 cm3 of acetic anhydride is again added and stirring is maintained for 24 h. The precipitate formed is spin-filter-dried and then washed with ethyl ether and pentane. This solid is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 μM), elution being carried out with a gradient of dichloromethane/methanol of 100/0 to 90/10. 41 mg of N-(3-chloro[1,2,4]triazolo[4,3-b]pyridazin-6-yl)acetamide are thus obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. temperatureis maintained for 24 h
  2. customThe precipitate formed
  3. customis spin-filter-dried
  4. washwashed with ethyl ether and pentane
  5. customThis solid is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A
  6. wash32-63 μM), elution

Sources & evidence

ORD record
ord-e556d77bad63402a9fad062dfd548f5d
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Reaction notes

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