Dimethylformamide → 6-Chloroimidazo[1,2-b]pyridazine-2-carbonyl chloride

HRID 1162424Notes

Reaction equation

HRID 1162424 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[N:7]=1.C(Cl)[Cl:15].C(Cl)(=O)C(Cl)=O.CN(C=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([Cl:15])=[O:13])[N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 27946376-Chloroimidazo[1,2-b]pyridazine-2-carboxylic acid

Product 1

HCID 577494296-Chloroimidazo[1,2-b]pyridazine-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a 250-mL, round-bottomed flask was added 6-chloroimidazo[1,2-b]pyridazine-2-carboxylic acid (2.0 g, 10 mmol, Maybridge, Cornwall, UK) and CH2Cl2 (40 mL). To the mixture was added oxalyl chloride (20 mL, 40 mmol, 2 M in CH2Cl2) and DMF (8.0 μL, 0.10 mmol). The mixture was stirred for 1.5 h at 25° C. Toluene (10 mL) was added and the mixture was concentrated to afford the title compound which was taken on to the next step without further purification.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-06e5b8e49de145c2b10ecf6ae2976c96
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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