ChemicalBook CAS DataBase List Furo[2,3-d]pyridazin-4-amine, 7-chloro-N-(4-chlorophenyl)-

Furo[2,3-d]pyridazin-4-amine, 7-chloro-N-(4-chlorophenyl)- synthesis

5synthesis methods

Product Name:Furo[2,3-d]pyridazin-4-amine, 7-chloro-N-(4-chlorophenyl)-
CAS Number:332013-40-8
Molecular formula:C12H7Cl2N3O
Molecular Weight:280.11

13177-70-3
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106-47-8 Synthesis

106-47-8
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Furo[2,3-d]pyridazin-4-amine, 7-chloro-N-(4-chlorophenyl)-

332013-40-8
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Furo[2,3-d]pyridazin-7-amine, 4-chloro-N-(4-chlorophenyl)-

332013-41-9
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Yield:-

Reaction Conditions:

in ethanol; for 4 h;Heating / reflux;

Steps:

9.5

A 100 mL round bottomed flask fitted with a stir bar, an argon inlet, and a reflux condenser was charged with the product of Step 4 (1.50 g, 7.98 mmol) dissolved in ethanol (40 mL). Chloroaniline was added to this mixture (1.02 g, 7.98 mmol), and the resultant suspension was warmed to reflux. After heating for 4 h, the mixture was concentrated by rotary evaporation. The crude orange solid was applied to the top of a flash column and eluted with CH₂Cl₂/MeOH 97:3 to afford a mixture of 4-chloro-7-[N-(4-chlorophenyl)amino][2,3-d]furopyridazine and 7-chloro-4-[N-(4-chlorophenyl)amino]-[2,3-d]furopyridazine as a yellow powder (1.2 g, 55 %). TLC (CH₂Cl₂/MeOH 97:3); R_f = 0.7; ¹H NMR (300 MHz, d₆-DMSO) δ major isomer (A) 7.40 (d, J = 8.9, 2), 7.45 (d, J = 2.0, 1), 7.87 (d, J = 9.2, 2), 8.34 (d, J = 2.0, 1) 9.62 (s, 1); minor isomer (B) 7.28 (d, J = 2.0, 1), 7.40 (d, J= 8.9, 2), 7.87 (d, J= 9.2, 2), 8.48 (d, J = 2.1, 1), 9.88 (s, 1).

References:

EP1228063,2009,B1 Location in patent:Page/Page column 39-40

4282-24-0 Synthesis