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CAS No.: 486460-32-6
Name: Sitagliptin
Article Data: 111
Molecular Structure:
Molecular Structure of 486460-32-6 (Sitagliptin)
Formula: C16H15F6N5O
Molecular Weight: 407.318
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)-;
EINECS: 690-730-1
Density: 1.61 g/cm3
Melting Point: 114.1-115.7 °C
Boiling Point: 529.9 °C at 760 mmHg
Flash Point: 274.3 °C
Appearance: yellow grease
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
ConditionsYield
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 methanol99%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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764667-65-4
654671-77-9
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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.

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

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