Acetyl chloride → HCID 10608542, compound

HRID 870762Notes

Reaction equation

HRID 870762 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([NH2:11])=[CH:9][N:10]=2)[N:7]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([NH:11][C:19](=[O:21])[CH3:20])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 107022736-Chloroimidazo[1,2-b]pyridazin-3-amine

Product 1

HCID 10608542HCID 10608542, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 6-chloroimidazo[1,2-b]pyridazin-3-amine and triethylamine (0.8 mL, 6.0 mmol) in DCM (25 mL) was added acetyl chloride dropwise and stirred at rt for overnight. The mixture was concentrated and purified by ISCO column chromatography (10% MeOH/DCM) to give not very pure N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)acetamide (500 mg, 95% yield). 60 mg of non-pure material was further purified by Prep HPLC (neutral) to give pure N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)acetamide. 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.01 (d, J=9.35 Hz, 1H), 7.94 (s, 1H), 7.26 (d, J=9.35 Hz, 1H), 2.29 (s, 3H); LRMS (ESI) m/e 210.9 [(M+H)+, calcd for C8H8ClN4O 211.6].

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by ISCO column chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-b2ad31cc21e04d098592d9314139aa17
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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