Sitagliptin supplier | CasNO.486460-32-6

Name
Sitagliptin
EINECS 690-730-1
CAS No. 486460-32-6
Article Data111
CAS DataBase
Density 1.61 g/cm³
Solubility
Melting Point 114.1-115.7 °C
Formula C₁₆H₁₅F₆N₅O
Boiling Point 529.9 °C at 760 mmHg
Molecular Weight 407.318
Flash Point 274.3 °C
Transport Information
Appearance yellow grease
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,2,4-Triazolo[4,3-a]pyrazine,7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-(9CI);(2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine;(3R)-3-amino-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo(4,3-a)pyrazin-7-yl)-4-(2,4,5-trifluorophenyl)butan-1-one;1-Butanone,3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-,(3R)-;
PSA 77.04000
LogP 2.65470

Synthetic route

: 1242069-63-1
(R)-benzyl (4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; under 760.051 Torr;	100%
With hydrogen; palladium-on-charcoal In tetrahydrofuran; water at 20℃; under 760.051 Torr;	100%
With hydrogen; palladium 10% on activated carbon In methanol	99%
With methylmagnesium bromide; hydrogen; palladium diacetate; nickel diacetate In water at 45℃; for 20h;	79%

: 1169707-28-1
7-(1-oxo-3((R)-amino)-4-(2,4,5-trifluorophenyl)butyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine di-p-tolyl-L-tartarate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With sodium hydroxide In ethyl acetate at 10℃; Product distribution / selectivity;	99.5%

: (3R)-3-[(benzyIoxy)amino]-l-[3-(trifluoromethyl)-5H,6H,7H,8H [1 ,2,4] triazolo [4,3-a] pyrazin-7-yl]-4-(2,4,5-trifluorophenyl) butan-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With formic acid; Pt/Al2O3; hydrogen In methanol at 20℃; Autoclave; Large scale;	97.8%
Stage #1: (3R)-3-[(benzyIoxy)amino]-l-[3-(trifluoromethyl)-5H,6H,7H,8H [1 ,2,4] triazolo [4,3-a] pyrazin-7-yl]-4-(2,4,5-trifluorophenyl) butan-1-one With hydrogenchloride; palladium 10% on activated carbon In ethanol; water at 30℃; under 2068.65 Torr; for 12 - 14h; Stage #2: With sodium hydroxide In ethanol; water at 12 - 14℃; pH=13; Stage #3: With phosphoric acid In ethanol; water at 45℃;	66%

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one With ammonium chloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(di-tert-butylphosphino)ferrocenyl]ethyl-di-2-methylphenylphosphine In methanol at 20℃; for 1h; Stage #2: With hydrogen In methanol at 50℃; under 5171.62 Torr; for 18h; Product distribution / selectivity;	97%
With di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium; hydrogen; (R,S)-t-bu Josiphos In methanol at 20 - 50℃; under 10343.2 Torr; for 14h;	93%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen; ammonium chloride In methanol at 50℃; under 13689.1 Torr; Inert atmosphere; enantioselective reaction;	82%

: C14H13F3N2O4

: 486460-21-3
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Reflux;	97%

: 486460-23-5
(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 20 - 25℃;	96.88%
With hydrogenchloride In methanol at 15 - 45℃; for 3h;	95.81%
With hydrogenchloride; methanol In water at 50℃; for 4h;	95%

: 1306610-49-0
C23H21F6N5O

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With Pt/Al2O3; hydrogen; acetic acid In methanol at 20℃; Autoclave; Large scale;	96.7%

: 486460-00-8
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In dichloromethane for 0.166667h; Stage #2: With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 25 - 30℃; for 4h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride Further stages;	96.5%

: 1380521-88-9
(R,R)-N-benzyl-N-(α-methylbenzyl)-1-(2',4',5'-trifluorophenyl)-4-oxo-4-{3''-(trifluoromethyl)-5'',6''-dihydro-1'',2'',4''-triazolo[4,3-α]pyrazin-7''(8''H)-yl}butan-2-amine

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 30% w/w Pd(OH)2/C; hydrogen In methanol under 3800.26 Torr; for 24h;	96%
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 50℃; under 19001.3 Torr; for 48h;	95%

: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

: 486460-00-8
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With thionyl chloride In ethyl acetate at 26℃; for 2h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride With triethylamine In ethyl acetate at 25℃; Solvent; Temperature;	96%
Stage #1: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride; (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With 1-methyl-1H-imidazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride In ethanol at 20℃; for 18h; Stage #3: With sodium hydroxide In ethanol; water pH=10 - 12; Time; Solvent;	90%
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With pivaloyl chloride; sodium carbonate In toluene Cooling; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride In toluene Stage #3: With hydrogenchloride In water; toluene Reagent/catalyst;	4.4 g

: Sitagliptin hydrochloride

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
In water at 20 - 25℃; pH=8 - 9; Alkaline conditions;	96%

: 823817-58-9
(2S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine dihydrogenphosphate salt

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With sodium hydroxide In water at 0 - 5℃; for 1h;	95%

: (4R)-4-(2,4,5-trifluorobenzyl)azetidin-2-one

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 2-Ethylhexanoic acid; triethylamine In tetrahydrofuran at 75℃; for 72h;	95%
With 2-Ethylhexanoic acid; triethylamine In tetrahydrofuran at 75℃; for 72h; Solvent; Temperature; Reagent/catalyst; Concentration;	95%

: 1169707-30-5
(3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid In methanol; water at 50℃; under 7500.75 Torr; for 14h;	94%
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol; water at 50℃; under 7500.75 Torr; for 14h;	81.2%
With formic acid; palladium(II) hydroxide/carbon In tetrahydrofuran; methanol; water at 60℃; for 6h;	79.4%

: sitagliptin phosphate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
In water at 20 - 25℃; pH=8 - 9; Alkaline conditions;	93.5%

: sitagliptin sulfate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
In water at 20 - 25℃; pH=8 - 9; Alkaline conditions;	93%

: 1169707-31-6
sitagliptin sulfate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
In water	92%

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione With ammonium formate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(di-tert-butylphosphino)ferrocenyl]ethyl-di-2-methylphenylphosphine In methanol at 55℃; for 5h; Stage #2: With hydrogen In methanol at 55℃; under 12929 Torr; for 20h; Product distribution / selectivity;	91%
Multi-step reaction with 3 steps 1: isopropyl alcohol; acetic acid / 18 h / 50 °C 2: sodium tetrahydroborate; acetic acid / tetrahydrofuran / 3 h / 20 °C 3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr View Scheme
Multi-step reaction with 3 steps 1: isopropyl alcohol; acetic acid / 18 h / 50 °C 2: sodium tetrahydroborate; formic acid / tetrahydrofuran / -30 °C 3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr View Scheme

: 1393363-87-5
(R)-N-benzyl-1-(2',4',5'-trifluorophenyl)-4-oxo-4-{3''-(trifluoromethyl)-5'',6''-dihydro-1'',2'',4''-triazolo[4,3-α]pyrazin-7''(8''H)-yl}butan-2-amine

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 20 wt.% Pd(OH)2 on activated carbon; hydrogen In methanol under 3800.26 Torr; for 24h;	91%

: 1349649-83-7
(R)-2-methyl-N-((R)-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4] triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)propane-2-sulfinamide

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With hydrogenchloride; methanol In water at 48℃;	91%
With hydrogenchloride In 1,4-dioxane at 20℃; for 4h; Solvent;	90.7%
With hydrogenchloride; water In methanol at 20℃; for 4h;	89%
With hydrogenchloride In water at 70℃; for 2h;	89%
With hydrogenchloride In methanol; water at 20℃; for 4h;

: C17H13F6N5O2

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: C17H13F6N5O2 With water In ethanol at 80℃; for 2h; Stage #2: With copper In quinoline; ethanol at 140℃; for 3h;	91%

: 1253055-98-9
(R)-3-azido-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (R)-3-azido-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one With triphenylphosphine In tetrahydrofuran at 50℃; for 2h; Stage #2: With ammonium hydroxide In tetrahydrofuran; water for 10h;	90%
Stage #1: (R)-3-azido-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one With triphenylphosphine In tetrahydrofuran at 50℃; for 2h; Stage #2: With ammonium hydroxide In tetrahydrofuran; water for 10h;	86%
With hydrogen; palladium on carbon In methanol for 6h;

: sitagliptin succinate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
In water at 20 - 25℃; pH=8 - 9; Alkaline conditions;	90%

: (R)-3-(((R)-1-phenylethyl)amino)-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one hydrochloride

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In water; isopropyl alcohol at 65 - 70℃; under 5430.2 Torr; for 8 - 10h; Inert atmosphere;	88%

: sitagliptin phosphate

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With ammonia In water at 25℃; pH=10; Product distribution / selectivity;	87.3%
With potassium hydroxide In tert-butyl methyl ether; water at 0 - 20℃; pH=11;	85%
With sodium hydroxide In water at 0 - 5℃; for 1h;
With sodium hydrogencarbonate; sodium chloride In water; ethyl acetate at 25 - 42℃; Reagent/catalyst; Temperature;	1.8 g

: 1351564-29-8
(R)-3-nitro-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (R)-3-nitro-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one With hydrogenchloride; zinc In methanol; water at 20℃; for 0.5h; Stage #2: With sodium hydroxide In methanol; water pH=10;	87%

: 1361389-75-4
3(R)-3-[(benzyloxy)amino]-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol; water at 50℃; under 2068.65 Torr; Large scale;	86%
Multi-step reaction with 2 steps 1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C 2: sodium hydroxide / water / 1 h / 0 - 5 °C View Scheme
With palladium 10% on activated carbon; hydrogen In ethanol; water at 50℃; under 2280.15 Torr; for 12h;

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 486460-21-3
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol In ethanol; dichloromethane at 10 - 25℃; for 3h;	86%

: 769195-20-2
(2S)-2({(1R)-3-oxo-1-(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]propyl}amino)-2-phenylethanamide

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid In methanol; water at 50℃; under 7500.75 Torr; for 14h;	85%

: sitagliptin phosphate

: 1169707-30-5
(3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one With formic acid; 10 wt% Pd(OH)2 on carbon In tetrahydrofuran; methanol for 6h; Reflux; Stage #2: With phosphoric acid In ethanol; water; ethyl acetate at 50 - 74℃; for 1.5h; Stage #3: sitagliptin phosphate In ethanol; water at 65℃; for 1h;	67.1%

Yield

Stage #1: (3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one With formic acid; 10 wt% Pd(OH)2 on carbon In tetrahydrofuran; methanol for 6h; Reflux;
Stage #2: With phosphoric acid In ethanol; water; ethyl acetate at 50 - 74℃; for 1.5h;
Stage #3: sitagliptin phosphate In ethanol; water at 65℃; for 1h;

67.1%

: 65-86-1
orotic acid

: 486460-32-6
sitagliptin

: 1246343-77-0
sitagliptin orotate

Conditions

Conditions	Yield
In acetonitrile at 25 - 75℃; Product distribution / selectivity;	99%
In water at 35 - 37℃; for 0.166667h;

: 486460-32-6
sitagliptin

: 654671-77-9
sitagliptin phosphate monohydrate

Conditions

Conditions	Yield
With phosphoric acid In water; isopropyl alcohol at 70 - 80℃; for 2h; Temperature;	97.7%
With phosphoric acid; water In isopropyl alcohol at 20 - 75℃;	95%
With phosphoric acid; water In isopropyl alcohol at 75℃;

: 611-71-2
(R)-Mandelic Acid

: 486460-32-6
sitagliptin

: 1240038-86-1
sitagliptin (R)-(-)mandelate

Conditions

Conditions	Yield
In ethyl acetate at 25 - 50℃; Product distribution / selectivity;	97%

: 486460-32-6
sitagliptin

: sitagliptin phosphate

Conditions

Conditions	Yield
With phosphoric acid In ethanol at 80℃; optical yield given as %ee;	96%
With phosphoric acid In ethanol at 80℃; for 0.5h;	96%
With phosphoric acid; water In isopropyl alcohol at 70 - 80℃;	96%

: 486460-32-6
sitagliptin

: 1253055-98-9
(R)-3-azido-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	96%

: 124-04-9
Adipic acid

: 486460-32-6
sitagliptin

: 1417158-34-9
(2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine adipic acid

Conditions

Conditions	Yield
In isopropyl alcohol at 25 - 50℃; for 0.5h;	95.9%
In isopropyl alcohol at 25 - 50℃;	95.9%
In ethanol at 25 - 80℃;	56.8%

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

: 486460-32-6
sitagliptin

: 837430-24-7
Sitagliptin fumarate

Conditions

Conditions	Yield
In methanol at 25 - 32℃; for 1h;	95%
In ethyl acetate; isopropyl alcohol at 25.5 - 26.7℃; for 0.683333h;	91%
In isopropyl alcohol at 30℃; Reflux;
In acetonitrile at 25 - 50℃; Product distribution / selectivity;
In butanone at 20℃; for 1h; Product distribution / selectivity;

: 17199-29-0
(S)-Mandelic acid

: 486460-32-6
sitagliptin

: sitagliptin L-mandelate

Conditions

Conditions	Yield
In ethanol	95%

: 486460-32-6
sitagliptin

: sitagliptin hydrogensulfate

Conditions

Conditions	Yield
With sulfuric acid In tert-butyl methyl ether; acetonitrile at 20℃;	95%
With sulfuric acid In acetonitrile at 25 - 50℃; Product distribution / selectivity;

: 486460-32-6
sitagliptin

: sitagliptin sulfate

Conditions

Conditions	Yield
With sulfuric acid In ethanol for 0.766667h;	94.8%

: 98-11-3
benzenesulfonic acid

: 486460-32-6
sitagliptin

: (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine besylate

Conditions

Conditions	Yield
In methanol at 25 - 32℃; for 1h;	93%
In Isopropyl acetate at 50℃; for 1h;
In Isopropyl acetate at 45 - 50℃;	0.63 g

: 486460-32-6
sitagliptin

: (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine phosphate

Conditions

Conditions	Yield
With phosphoric acid In water; isopropyl alcohol at 20 - 60℃; for 1.5h;	92.6%
With phosphoric acid In methanol
With phosphoric acid In water; isopropyl alcohol at 25 - 78℃;	6.7 g

: 486460-32-6
sitagliptin

: Sitagliptin hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 0.75h;	92.4%
With hydrogenchloride In isopropyl alcohol at 30℃; for 3h;
With isopropyl alcohol hydrogen chloride In methanol; diethyl ether at 25 - 45℃; for 1h;	1.1 g
With hydrogenchloride In water; ethyl acetate at 0 - 65℃; Solvent; Temperature;	102 g
With hydrogenchloride In isopropyl alcohol at 50℃; Temperature; Solvent;	10.3 g

: 6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7
D-glucuronic acid

: 486460-32-6
sitagliptin

: sitagliptin D-glucuronate

Conditions

Conditions	Yield
In methanol; water; isopropyl alcohol at 20℃;	92%

Sitagliptin History

Sitagliptin was approved by the U.S. Food and Drug Administration (FDA) on October 17, 2006 and is marketed in the US as Januvia by Merck & Co. On April 2, 2007, the FDA approved an oral combination of sitagliptin and metformin marketed in the US as Janumet.

Sitagliptin Specification

Sitagliptin(CAS NO.486460-32-6), its Synonyms are Januvia; 1,2,4-Triazolo(4,3-a)pyrazine, 7-((3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl)-5,6,7,8-tetrahydor-3-(trifluoromethyl)-; Xelevia. It belongs to the Product Categories of API; Pharmaceutical intermediate. Sitagliptin is used either alone or in combination with other oral antihyperglycemic agents (such as metformin or a thiazolidinedione) for treatment of diabetes mellitus type 2.

Physical properties about Sitagliptin are: (1)ACD/LogP: 2.055; (2)ACD/LogD (pH 5.5): 0.64; (3)ACD/LogD (pH 7.4): 1.93; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 16.25; (6)ACD/KOC (pH 5.5): 12.00 ; (7)ACD/KOC (pH 7.4): 236.58; (8)#H bond acceptors: 6; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.59; (12)Molar Refractivity: 85.18 cm³; (13)Molar Volume: 252.363 cm³; (14)Polarizability: 33.768 10-24cm³; (15)Surface Tension: 42.4780006408691 dyne/cm; (16)Density: 1.614 g/cm³; (17)Flash Point: 274.277 °C ; (18)Enthalpy of Vaporization: 80.506 kJ/mol; (19)Boiling Point: 529.905 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1;
(2)InChIKey=MFFMDFFZMYYVKS-SECBINFHSA-N;
(3)Smilesc1(c(F)cc(c(F)c1)C[C@H](CC(N1CCn2c(C1)nnc2C(F)(F)F)=O)N)F

Product Name

Sitagliptin

Synthetic route

Sitagliptin History

Sitagliptin Specification

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