CAS No.171596-29-5,Tadalafil Suppliers

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Basic Information

Molecular Structure:
CAS No.:	171596-29-5
Name:	Tadalafil
Article Data:	48
Cas Database

Formula:	C₂₂H₁₉N₃O₄
Molecular Weight:	389.411
Synonyms:	Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione,6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-;(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;GF 196960;Tadalafil [USAN];Tildenafil;Calais;(6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione;Adcirca;
EINECS:	200-835-2
Density:	1.51 g/cm³
Melting Point:	298-300 °C
Boiling Point:	679.1 °C at 760 mmHg
Flash Point:	364.5 °C
Appearance:	white to off-white cyrstalline solid
Hazard Symbols:	F,Xn
Risk Codes:	11-20/21/22-36
Safety:	16-36/37
PSA:	74.87000
LogP:	2.08710

Synthetic route

: C22H19ClN2O5*(x)ClH

: 74-89-5
methylamine

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In dichloromethane at 0 - 5℃; for 3h; Temperature; Solvent;	99.3%

: 74-89-5
methylamine

: 171489-59-1
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃;	95%
In N,N-dimethyl-formamide at 20℃; for 10h;	95%
In methanol for 3h; Reflux; Large scale;	95.3%

: (6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione

: 74-95-3
1,2-dibromomethane

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 6h;	95%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	93%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	93%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	93%

: 1224724-00-8
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With hydrogen; Raney Ni In ISOPROPYLAMIDE at 80℃; under 2280.15 Torr; for 22h; Product distribution / selectivity;	94%

: 171489-59-1
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With methylamine In dichloromethane for 2h;	93.5%
With methylamine In water for 20h; Ionic liquid;	355 mg

: 52605-49-9
sarcosine ethyl ester hydrochloride

: (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With potassium carbonate In ethylene glycol at 110℃; Solvent; Reagent/catalyst; Temperature; Green chemistry;	92.7%

: 749864-18-4
1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With piperidine In N,N-dimethyl-formamide at 20℃; for 1h;	92%

: C22H20N4O3

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: C22H20N4O3 With sulfuric acid In isopropyl alcohol for 12h; Reflux; Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 8h; Temperature;	91.2%

: (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-carboxylic acid

: 74-89-5
methylamine

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In tetrahydrofuran; water at 50℃; Solvent; Temperature;	91%

: 107-97-1
sarcosine

: (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: sarcosine; (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride With triethylamine In tetrahydrofuran at 30℃; for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Solvent; Reagent/catalyst; Temperature; Further stages;	90.54%

Raw Materials

120-57-0

593-51-1

79-04-9

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Chemistry

The Molecular Structure of Tadalafil (CAS NO.171596-29-5):

Empirical Formula: C₂₂H₁₉N₃O₄
Molecular Weight: 389.404
Appearance: Off-White Cyrstalline Solid
Nominal Mass: 389 Da
Average Mass: 389.404 Da
Monoisotopic Mass: 389.137556 Da
Index of Refraction: 1.758
Molar Refractivity: 105.27 cm³
Molar Volume: 256.2 cm³
Surface Tension: 81.5 dyne/cm
Density: 1.51 g/cm³
Flash Point: 364.5 °C
Enthalpy of Vaporization: 99.67 kJ/mol
Boiling Point: 679.1 °C at 760 mmHg
Vapour Pressure: 2.67E-18 mmHg at 25°C
Melting Point: 298-300°C
Product Categories: Active Pharmaceutical Ingredients;Cnbio;Erectile Dysfunction;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API's
InChI: InChI=1/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
Smiles: C1N(C([C@H]2Cc3c([C@H](N2C1=O)c1ccc2c(c1)OCO2)[nH]c1ccccc31)=O)C

History

Tadalafil (CAS NO.171596-29-5) was discovered by Glaxo Wellcome (now GlaxoSmithKline) under a partnership between Glaxo and ICOS to develop new drugs that began in August 1991. In December 2003, after sildenafil (Viagra) and vardenafil (Levitra),the Food and Drug Administration approved tadalafil (as Cialis) for sale in the United States as the third ED prescription drug pill. Then in May 2009,Tadalafil was approved in the United States for the treatment of pulmonary arterial hypertension and is currently under regulatory review in other regions for this condition.

Uses

Tadalafil (CAS NO.171596-29-5) can be used for the treatment of erectile dysfunction under the name Cialis. Recently Tadalafil (CAS NO.171596-29-5) has been approved for the treatment of pulmonary arterial hypertension and other onditions.

Safety Profile

The most common side effects of tadalafil are: are headache, indigestion, flushing,back pain, muscle aches and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to vasodilate (cause blood vessels to widen), these usually go away after a few hours. Back pain and muscle aches maybe occur 12 to 24 hours after taking the drug,and the symptom usually disappears after 48 hours.

Specification

Tadalafil (CAS NO.171596-29-5) is the main raw materials of Cialis,compare with Sildenafil,Tadalafil have less side effects, after taking two days,30% of people have muscles ache feeling (mainly waist and legs). It is also called as Tadalafil [USAN] ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; Adcirca ; Cialis ; Tadalafil ; Tadalafil Lilly ;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)- ; Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)- .

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