ChemicalBook CAS DataBase List 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester synthesis

7synthesis methods

Product Name:6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester
CAS Number:1150566-27-0
Molecular formula:C9H8ClN3O2
Molecular Weight:225.63

Pyridazinium, 3-chloro-6-[[(dimethylamino)methylene]amino]-1-(2-ethoxy-2-oxoethyl)-, bromide (1:1)

1150566-26-9

6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

1150566-27-0

General procedure for the synthesis of ethyl 6-chloroimidazo[1,2-B]pyridazine-3-carboxylate from the compound (CAS:1150566-26-9): S-chloro-β-dimethylamino-methyleneamino-J-isoethyloxycarbonylmethyl-pyridazine-1-bromide (11.40 g, 32.40 mmol) was dissolved in acetonitrile (200 mL), followed by addition of diisopropylethylamine (15.22 mL, 64.81 mmol). The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was ground with water to afford 5.77 g of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate as a light brown solid in 77% yield. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 8.36 (1H, s), 8.01 (1H, d, J = 9.4 Hz), 7.27 (1H, d, J = 9.4 Hz), 4.46 (2H, q, J = 7.1 Hz), 1.37 (3H, t, J = 7.1 Hz).LCMS analysis showed m/z 226 [M + 1]+ (molecular weight: 225.64).

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1150566-27-0
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Yield:1150566-27-0 77%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in acetonitrile at 20; for 4 h;

Steps:

2

Intermediate 2 6-Chloro-imidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester; S-Chloro-β^dimethylamino-methyleneaminoJ-i-ethoxycarbonylmethyl-pyridazin- 1-ium bromide (11.40 g, 32.40 mmol) was dissolved in acetonitrile (200 mL) and diisopropylethylamine (15.22 mL, 64.81 mmol) was added. The reaction mixture was stirred for 4 hours at room temperature. The solvent was removed in vacuo and the residue was triturated from water to give 5.77 g of 6-chloro-imidazo[1 ,2- b]pyridazine-3-carboxylic acid ethyl ester as a pale brown solid (77% yield). 1H NMR (300 MHz, CDCI₃): δ 8.36 (1 H, s), 8.01 (1H, d, J = 9.4 Hz), 7.27 (1H, d, J = 9.4 Hz), 4.46 (2H, q, J = 7.1 Hz)₁ 1.37 (3H, W = 7.1 Hz). LCMS: 226 [M+1J. (MW: 225.64)

References:

WO2009/60197,2009,A1 Location in patent:Page/Page column 59

5469-69-2 Synthesis