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| | Chloropretadalafil Basic information |
| Product Name: | Chloropretadalafil | | Synonyms: | (1R,3R)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (Chloropretadalafil);(1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(chloroacetyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylic acid methy ester;1H-Pyrido[3,4-b]indole-3-carboxylic acid, 1-(1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-, methyl ester, (1R,3R)-;B]indole-3-carboxylate;(1R,3R)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3;(1R,3R)-1-(1,3-BENZODIOXOL-5-YL)-2-(CHLOROACETYL)-2,3,4,9-TETRAHYDRO-1H-PYRIDO[3,4-B] INDOLE-3-CARBOXYLIC ACID METHYL ESTER;(1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-2-CHLOROACETYL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE;(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester | | CAS: | 171489-59-1 | | MF: | C22H19ClN2O5 | | MW: | 426.85 | | EINECS: | | | Product Categories: | Intermediate of Tadalafil;Chiral Reagents | | Mol File: | 171489-59-1.mol |  |
| | Chloropretadalafil Chemical Properties |
| Melting point | 230-232℃ | | Boiling point | 627.5±55.0 °C(Predicted) | | density | 1.445 | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly) | | pka | 16.25±0.60(Predicted) | | form | Solid | | color | White to Pale Orange | | InChI | InChI=1S/C22H19ClN2O5/c1-28-22(27)16-9-14-13-4-2-3-5-15(13)24-20(14)21(25(16)19(26)10-23)12-6-7-17-18(8-12)30-11-29-17/h2-8,16,21,24H,9-11H2,1H3/t16-,21-/m1/s1 | | InChIKey | JUKHNCNDFOAFLT-IIBYNOLFSA-N | | SMILES | N1C2=C(C=CC=C2)C2C[C@H](C(OC)=O)N(C(CCl)=O)[C@H](C3=CC=C4OCOC4=C3)C1=2 |
| | Chloropretadalafil Usage And Synthesis |
| Description | Chloropretadalafil is a key synthetic intermediate of tadalafil which is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). | | Chemical Properties | White Solid | | Uses | (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. | | References | [1] ALAIN DAUGAN. The Discovery of Tadalafil: A Novel and Highly Selective PDE5 Inhibitor. 2: 2,3,6,7,12,12a-hexahydropyrazino[1‘,2‘:1,6]pyrido[3,4-b]indole-1,4-dione Analogues[J]. Journal of Medicinal Chemistry, 2003. DOI:10.1021/jm0300577.
[2] SHI X X, LIU S, XU W Z, et al. Highly stereoselective Pictet–Spengler reaction of d-tryptophan methyl ester with piperonal: convenient syntheses of Cialis (Tadalafil), 12a-epi-Cialis, and their deuterated analogues[J]. Tetrahedron-asymmetry, 2008, 19: 435-442. DOI:10.1016/J.TETASY.2007.12.017.
[3] ZHANG Y, HE Q, DING H, et al. IMPROVED SYNTHESIS OF TADALAFIL[J]. Organic Preparations and Procedures International, 2005, 37: 102-199. DOI:10.1080/00304940509355408. |
| | Chloropretadalafil Preparation Products And Raw materials |
| Raw materials | Chloroacetyl chloride-->(1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE-->(1S,3R)-Methyl-1,2,3,4-tetrahydro-1-(3,4-Methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate-->Piperonyl alcohol | | Preparation Products | cis-Tadalafil-->Nortadalafil-->Tadalafil |
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