Ticagrelor supplier | CasNO.274693-27-5

Name
Ticagrelor
EINECS 619-540-9
CAS No. 274693-27-5
Article Data62
CAS DataBase
Density 1.676 g/cm³
Solubility
Melting Point
Formula C₂₃H₂₈F₂N₆O₄S
Boiling Point 777.551 °C at 760 mmHg
Molecular Weight 522.576
Flash Point 424.048 °C
Transport Information
Appearance white powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms AR-C126532XX;AZD 6140;1,2-Cyclopentanediol,3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)-,(1S,2S,3R,5S)-;
PSA 163.74000
LogP 2.08670

Synthetic route

: 274693-26-4
[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol at -3 - 20℃; for 3h; Large scale;	97.1%
With hydrogenchloride In methanol at 0 - 10℃; for 2h; Temperature; Large scale;	95%
With hydrogenchloride In water; ethyl acetate	94.1%

: N-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)-3-((3aS,4R,6S,6aR)-2,2-dimethyl-6-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-5-(propylthio)-3H-[1,2,3]triazol[4,5-d]pyrimidin-7-amine

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 0 - 20℃; for 4.5h;	97%
With hydrogenchloride In methanol; water at 15 - 25℃; for 3h;	86%

: (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine

: 1354945-69-9
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	96%
With triethylamine In tetrahydrofuran at 20℃; for 2h;	96%

: C9H9F2N*ClH

: 1354945-69-9
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 25 - 35℃; Product distribution / selectivity;	95.5%

: C30H34F2N6O4S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 3000.3 Torr; for 2h;	95.2%

: 1354945-69-9
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine

: (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 24h;	95%

: 1402150-10-0
(4-{7-[2-(3,4-difluorophenyl)cyclopropylamino]-5-propylsulfanyl-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl}-2,3-dihydroxycyclopentyloxy)acetic acid ethyl ester

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With sodium tetrahydroborate In water at 20℃; for 3h; Time;	93.8%
With sodium tetrahydroborate In diethylene glycol dimethyl ether at 50 - 60℃; for 3h; Large scale;	0.5 kg

: 1354945-69-9
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine

: 1444301-72-7
(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine mandelate

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile at 20℃; for 20h;	93%
With sodium carbonate In acetonitrile at 20℃; for 20h;	93%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 5 - 20℃; for 5h;	80.24%
Stage #1: (1R,2S)-2-(3,4-difluorophenyl)cyclopropanammonium mandelate With N-ethyl-N,N-diisopropylamine; sodium hydroxide In water; ethyl acetate at 15 - 20℃; Stage #2: 9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine With N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 1h;	67%

: C30H40F2N6O4S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 15 - 25℃; for 3h;	93%

: C33H38F2N6O4S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 55℃; Temperature;	92%

: C44H46F2N6O4S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With pyridine hydrochloride at 0℃;	91%

: 1383715-61-4
tert-butyl N-[3-[(3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]carbamate

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With phosphoric acid In ethanol at 20℃; for 24h; Reagent/catalyst; Solvent;	87%
With phosphoric acid In ethanol; water at 20℃; for 24h;	87%
Stage #1: tert-butyl N-[3-[(3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]carbamate With hydrogenchloride; water In methanol; toluene at 25 - 30℃; for 2h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate pH=> 8;
Multi-step reaction with 4 steps 1.1: iodine / acetone / 2 h / 25 - 60 °C 2.1: potassium carbonate / acetone / 20 h / 55 - 60 °C 3.1: hydrogenchloride; water / methanol / 5 h / 20 - 25 °C 3.2: 25 - 30 °C / pH 10 4.1: formic acid / palladium 10% on activated carbon / 50 °C View Scheme

: 376608-71-8
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt

: 1354945-69-9
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran at 20 - 30℃; for 3h; Reagent/catalyst; Solvent;	87%
With potassium carbonate In acetonitrile at 25 - 30℃;	62.19%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 25 - 30℃; for 4h;	2.29 g

: 1354945-69-9
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine

: (1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine mandelate

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane; water at 20℃; for 4h;	86.2%

: C31H42F2N6O6S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With trifluoroacetic acid In methanol at 60℃;	86%

: C24H26F2N6O5S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 30℃; Cooling with ice;	85.2%
With sodium hydroxide In 1,4-dioxane; water at 20 - 30℃;	85.2%

: C32H46F2N6O4SSi

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 30℃; for 24h;	85%

: 1427524-43-3
tert-butyl ((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)(3-((1R,2S,3S,4S)-2,3-dihydroxy-4-(2-hydroxyethoxy)cyclopentyl)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)carbamate

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With phosphoric acid In methanol; water at 20℃; for 24h;	84%

: C33H44F2N6O6S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 55℃;	84%

: C38H46F2N6O6S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 50℃;	83%

: C31H40F2N6O6S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 0.5h; Reagent/catalyst; Solvent;	82.5%
With hydrogenchloride In methanol; water at 0 - 20℃; for 2h; Inert atmosphere;	78.2%

: C30H40F2N6O5S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 15 - 25℃; for 3h;	82%

: 2-(((3aS,4S,6R,6aS)-6-(7-((2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2-phenyltetrahydro-4H-cyclopenta[d][1,3,2]dioxaborol-4-yl)oxy)ethan-1-ol

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With dihydrogen peroxide In ethyl acetate at 20℃; for 1h;	81%

: C28H36F2N6O5S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 15 - 25℃; for 3h;	78%

: (x)C3H7NO*C23H28F2N6O4S

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
Stage #1: (x)C3H7NO*C23H28F2N6O4S In isopropyl alcohol; acetonitrile at 65 - 70℃; Stage #2: With pyrographite at 0 - 70℃; for 2h;	77.6%

: 2-(((3aS,4S,6R,6aS)-2-(3-(benzyloxy)phenyl)-6-(7-((2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)tetrahydro-4H-cyclopenta[d][1,3,2]dioxaborol-4-yl)oxy)ethan-1-ol

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With dihydrogen peroxide In ethyl acetate at 20℃; for 1h;	77%

: 2-(((3aS,4S,6R,6aS)-2-cyclohexyl-6-(7-((2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)tetrahydro-4H-cyclopenta[d][1,3,2]dioxaborol-4-yl)oxy)ethan-1-ol

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With dihydrogen peroxide In ethyl acetate at 20℃; for 1h;	76%

: 1383715-59-0
2-[[(3aR,4S,6R,6aS)-6-[[4-[N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-yl]-N-tert-butoxycarbonyl]amino]-2-(propylthio)-5-nitropyrimidin-6-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy] ethanol

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
Stage #1: 2-[[(3aR,4S,6R,6aS)-6-[[4-[N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-yl]-N-tert-butoxycarbonyl]amino]-2-(propylthio)-5-nitropyrimidin-6-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy] ethanol With acetic acid; zinc In dichloromethane at 5 - 10℃; for 2h; Stage #2: With acetic acid; sodium nitrite In dichloromethane; water at 0 - 3℃; for 2h; Stage #3: With hydrogenchloride In methanol; water for 4h;	74%
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 2.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 3.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 3.2: pH > 8 View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 2.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 3.1: potassium carbonate / acetone / 24 h / 25 - 60 °C 4.1: hydrogenchloride; water / methanol / 5.5 h / 20 - 55 °C 4.2: 25 - 30 °C / pH 10 View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 2.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 3.1: iodine / acetone / 2 h / 25 - 60 °C 4.1: potassium carbonate / acetone / 20 h / 55 - 60 °C 5.1: hydrogenchloride; water / methanol / 5 h / 20 - 25 °C 5.2: 25 - 30 °C / pH 10 6.1: formic acid / palladium 10% on activated carbon / 50 °C View Scheme

: 2-(((3aS,4S,6R,6aS)-2-(4-chlorophenyl)-6-(7-((2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)tetrahydro-4H-cyclopenta[d][1,3,2]dioxaborol-4-yl)oxy)ethan-1-ol

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With dihydrogen peroxide In ethyl acetate at 20℃; for 1h;	71%

: N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]-N-{3-[(3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl}-N’,N’-dimethylsulfuric diamide

: 274693-27-5
ticagrelor

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 6.5h;	67%

: 274693-27-5
ticagrelor

: C23H27F2N7O6S

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water; acetonitrile at 10℃; for 40h; Solvent; Temperature;	94.8%

: 274693-27-5
ticagrelor

: 110-17-8
(2E)-but-2-enedioic acid

: (1S,2S,3R,5S)-3-[7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylthio)-3H-[1,2,3]-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxyl)cyclopentane-1,2-diol fumarate

Conditions

Conditions	Yield
In n-heptane; acetone at 0 - 35℃; for 1h; Solvent; Temperature;	94.4%
In acetone at 25 - 30℃;	65%

: 274693-27-5
ticagrelor

: 77-76-9
2,2-dimethoxy-propane

: 274693-26-4
[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20 - 30℃; for 12h; Inert atmosphere;	93%

: 274693-27-5
ticagrelor

: 110-15-6
succinic acid

: (1S,2S,3R,5S)-3-[7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylthio)-3H-[1,2,3]-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxyl)cyclopentane-1,2-diol succinate

Conditions

Conditions	Yield
In acetone at 25 - 30℃;	81%

: 274693-27-5
ticagrelor

: 50-78-2
aspirin

: C9H8O4*C23H28F2N6O4S

Conditions

Conditions	Yield
In hexane; dichloromethane at 20℃; for 264h; Product distribution / selectivity;	78%

Ticagrelor Chemical Properties

Molecular Structure of Ticagrelor (CAS NO.274693-27-5):

Molecular Formula: C₂₃H₂₈F₂N₆O₄S
Molecular Weight: 522.57
IUPAC Name: (1S,2S)-3-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-propylsulfanyltriazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
Synonyms of Ticagrelor (CAS NO.274693-27-5): (1S,2S,3R,5S)-3-(7-((1R,2S)-2-(3,4-Difluorophenyl)cyclopropylamino)-5-(propylthio)-3H-(1,2,3)triazolo(4,5-d)pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol ; AR-C126532XX ; AZD6140 ; Brilinta ; UNII-GLH0314RVC ; 1,2-Cyclopentanediol, 3-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(2-hydroxyethoxy)-, (1S,2S,3R,5S)-
CAS NO: 274693-27-5
Product Categories: Prevention of thromboembolic events in patients with acute coronary syndrome
Density of Ticagrelor (CAS NO.274693-27-5): 1.67

Product Name

Ticagrelor

Synthetic route

Ticagrelor Chemical Properties

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