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

HRID 517807Notes

Reaction equation

HRID 517807 reaction equation
[CH3:1][C:2](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:3].[Cl:25][C:26]1[N:30]2[N:31]=[C:32]([NH2:35])[CH:33]=[CH:34][C:29]2=[N:28][N:27]=1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[Cl:25][C:26]1[N:30]2[N:31]=[C:32]([NH:35][C:2](=[O:3])[CH3:1])[CH:33]=[CH:34][C:29]2=[N:28][N:27]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 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 anhyhdride 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-746a850dcfc34738b4e25b0cec2aee82
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

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