ChemicalBook > CAS DataBase List > Chloropretadalafil

Chloropretadalafil

Product Name
Chloropretadalafil
CAS No.
171489-59-1
Chemical Name
Chloropretadalafil
Synonyms
(6R,12aR)-methyl1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(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-carboxylicacidmethyeste;TDF-M2;Tadanafil P-1;Methyl (1R,3R;Chloropretadalafil;adalafil impurity 1;Tadaafil Intermediate;B]indole-3-carboxylate
CBNumber
CB5116504
Molecular Formula
C22H19ClN2O5
Formula Weight
426.85
MOL File
171489-59-1.mol
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Chloropretadalafil Property

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)
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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

TRC
Product number
M330125
Product name
(1R,3R)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate(Chloropretadalafil)
Packaging
2g
Price
$185
Updated
2021/12/16
AK Scientific
Product number
Z2024
Product name
(1R,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloroethanoyl)2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylicacidmethylester
Packaging
5g
Price
$109
Updated
2021/12/16
AK Scientific
Product number
Z2024
Product name
(1R,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloroethanoyl)2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylicacidmethylester
Packaging
10g
Price
$149
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0028594
Product name
CHLOROPRETADALAFIL
Purity
95.00%
Packaging
5MG
Price
$459.06
Updated
2021/12/16
Matrix Scientific
Product number
095485
Product name
(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
Purity
95+%
Packaging
1g
Price
$16
Updated
2021/12/16
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Chloropretadalafil Chemical Properties,Usage,Production

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

Preparation Products

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View Lastest Price from Chloropretadalafil manufacturers

Zibo Hangyu Biotechnology Development Co., Ltd
Product
Chloropretadalafil 171489-59-1
Price
US $45.00-450.00/KG
Min. Order
1KG
Purity
0.99
Supply Ability
20 tons
Release date
2023-10-20
Shandong Luning Pharmaceutical Co., Ltd.
Product
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-B]indole-3-carboxylate 171489-59-1
Price
US $171.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
6000KG
Release date
2020-10-22
PNP Biotech Co. Ltd
Product
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-B]indole-3-carboxylate 171489-59-1
Price
US $0.00/KG
Min. Order
25KG
Purity
98%-99%
Supply Ability
Inquiry
Release date
2022-10-21

171489-59-1, ChloropretadalafilRelated Search:

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2,2-dichloroacetyl) -2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate cis-Octahydroisoindole (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine (1S,3S)-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 2-Hydroxypropyl Nortadalafil Tadalafil EP Impurity N-Octyl Nortadalafil (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester 1,1'-Ethylidenebis(tryptophan) (1R,3R)-2-acetyl-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro- 1H-pyrido[3,4-b]indole-3-carboxylate Amino Tadalafil Tadalafil (1R,3S)-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 Tadalafil KetolactaM Tadalafil iMpurity B D(+)-Tryptophan (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester (6R,trans)-6-(3,4-dihydroxyphenyl)-2,3,6,7,12,12a-hexahydro-2-Methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

  • (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylicacidmethyeste
  • (6R,12aR)-methyl1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
  • (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(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 (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
  • (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
  • Tadalafil IMpurity: IMpurity E
  • (1R,3R)-Methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b
  • (6R, 12aR)-methyl 1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4- Tadalafil methylenedioxyphenyl)-9H-pyridol[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)- methyl -1,2,3,4-tetrahydro-1-(3,4- methylenedioxyphenyl)-9H-pyrido [3,4-B]indole-3-carboxyl
  • Tadanafil P-1
  • Tadalafil Chloroacetyle Impurity
  • (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic
  • Chloropretadalafil (Methyl (1R,3R)-
  • 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
  • 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
  • Methyl (1R,3R
  • Tadalafil intermediates，(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-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-meth...
  • An intermediate in the synthesis of Tadalafil, which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.
  • Intermediate of Tadalafil 3
  • (1R,3R)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]"
  • Methyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-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)
  • TDF-M2
  • YL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE
  • Tadaafil Intermediate
  • adalafil impurity 1
  • (1R3R)-METHYL-1,23.4-TETRAHYDRO-2-CHLOROACETL-1-(3.4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3.4-BJINDOLE-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
  • Chloropretadalafil
  • (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
  • 171489-59-1
  • Intermediate of Tadalafil
  • Chiral Reagents