ChemicalBook CAS DataBase List Chloropretadalafil

Chloropretadalafil synthesis

5synthesis methods

Product Name:Chloropretadalafil
CAS Number:171489-59-1
Molecular formula:C22H19ClN2O5
Molecular Weight:426.85

(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylic is used as an intermediate in the synthesis of Tadafil, which is used for the treatment of erectile dysfunction. It can be synthesized by (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl )-9H-pyrido[3,4-b]indole-3-carboxylate reacts with chloroacetyl chloride.

79-04-9 Synthesis

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(1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE

171596-41-1
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171489-59-1
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Yield:171489-59-1 95.2%

Reaction Conditions:

Stage #1: (1R,3R)-1-(benzo[1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl esterwith triethylamine in dichloromethane at 20; for 0.166667 h;Large scale;
Stage #2: chloroacetyl chloride in dichloromethane at 20; for 1 h;Large scale;

Steps:

13-19 Synthesis of intermediate 3

Put intermediate 2 (20kg, 52mol), 160L of dichloromethane, Add to 500L reaction kettle, Stir at room temperature, Add triethylamine (13.6kg, 134mol), Stir for 10min, 10 L of a solution of chloroacetyl chloride (8.2 kg, 73 mol) in dichloromethane was added dropwise, After finishing, Reaction at room temperature for 1h, The reaction was detected by HPLC. Add 170L of water, A large amount of solids precipitated, Stir at -10 for 0.5h-1h, Slightly sticky, centrifuge, Wash with a small amount of dichloromethane, The product is dried to obtain 21kg of intermediate 3 white solid, The yield was 95.2%, and the purity was 99.1%.

References:

CN110437228,2019,A Location in patent:Paragraph 0062-0082

79-04-9 Synthesis

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