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171489-59-1

171489-59-1 Structure

171489-59-1 Structure
IdentificationBack Directory
[Name]

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

171489-59-1
[Synonyms]

TDF-M2
Methyl (1R,3R
Tadanafil P-1
Chloropretadalafil
adalafil impurity 1
Tadaafil Intermediate
B]indole-3-carboxylate
Intermediate of Tadalafil 3
Tadalafil IMpurity: IMpurity E
Tadalafil Chloroacetyle Impurity
Chloropretadalafil (Methyl (1R,3R)-
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-meth...
YL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-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)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]"
(1R,3R)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b
(1R,3R)- methyl -1,2,3,4-tetrahydro-1-(3,4- methylenedioxyphenyl)-9H-pyrido [3,4-B]indole-3-carboxyl
Methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic
Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetra-hydro-1H-pyrido[3,4-b]indole-3-carboxylate
(1R3R)-METHYL-1,23.4-TETRAHYDRO-2-CHLOROACETL-1-(3.4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3.4-BJINDOLE-3-CARBOXYLATE
(1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-2-CHLOROACETYL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE
(1R,3R)-Methyl 1-(1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-Pyrido[3,4-b]indole-3-carboxylate
(6R,12aR)-methyl1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
(6R.12aR)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl1-1(3,4-Methylenedioxyphenyl)9H-pyrido-[3,4-b]-indole-3-Carbxylate
(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylicacidmethyeste
methyl(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-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[3,4-b]indole-3-carboxylate
(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
(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)-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)-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
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)-
(6R, 12aR)-methyl 1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4- Tadalafil methylenedioxyphenyl)-9H-pyridol[3,4-b]indole-3- carboxylate
Chloropretadalafil (Methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido-[3,4-b]indole-3-carboxylate)
(1R, 3R) -1- (1,3-benzodioxolane 5-yl) -2- (chloroacetyl) -2,3,4,9-tetrahydro-1H-pyridino [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 (Chloropretadalafil)
An intermediate in the synthesis of Tadalafil, which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.
Tadalafil intermediates,(1R,3R)-methyl-1,2,3,4-tetrahydro-2- chloroacetyl-1-(3,4- methylenedioxyphenyl)-9H-pyrido[3,4- B]indole-3-carboxylate
[Molecular Formula]

C22H19ClN2O5
[MDL Number]

MFCD04973633
[MOL File]

171489-59-1.mol
[Molecular Weight]

426.85
Chemical PropertiesBack Directory
[Melting point ]

230-232℃
[Boiling point ]

627.5±55.0 °C(Predicted)
[density ]

1.445
[storage temp. ]

-20°C Freezer, Under Inert Atmosphere
[solubility ]

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
[form ]

Solid
[pka]

16.25±0.60(Predicted)
[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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H335-H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Raw materials And Preparation ProductsBack Directory
[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
Hazard InformationBack Directory
[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.
[Uses]

An intermediate in the synthesis of Tadalafil (T004500), which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.
[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.
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