Alogliptin supplier | CasNO.850649-61-5

Name
ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)
EINECS 821-899-3
CAS No. 850649-61-5
Article Data28
CAS DataBase
Density 1.342 g/cm³
Solubility
Melting Point
Formula C₁₈H₂₁N₅O₂
Boiling Point 519.238 °C at 760 mmHg
Molecular Weight 339.397
Flash Point 267.826 °C
Transport Information
Appearance White powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-[[6-[(3R)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;UNII-JHC049LO86;CHEMBL376359;CID11450633;2-({6-[(3r)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile;
PSA 97.05000
LogP 1.15978

Synthetic route

: 3-(R)-aminopiperidine dihydrochloride

: 865758-96-9
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
With potassium hydrogencarbonate In isopropyl alcohol; acetonitrile at 60℃; for 6h;	92.7%
With triethylamine In isopropyl alcohol at 65℃; for 17h;	85%
With tetra-n-butylphosphonium chloride; sodium hydrogencarbonate In water; toluene at 60 - 70℃; Solvent; Temperature;	85.7%

: 309956-78-3
(R)-piperidin-3-ylcarbamic acid tert-butyl ester

: 865758-96-9
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Stage #1: 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: (R)-piperidin-3-ylcarbamic acid tert-butyl ester With triethylamine In N,N-dimethyl-formamide at 23℃; for 2h; Schlenk technique; Inert atmosphere; Stage #3: With trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide at 23℃; for 1h; Schlenk technique; Inert atmosphere;	92%

Yield

Stage #1: 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: (R)-piperidin-3-ylcarbamic acid tert-butyl ester With triethylamine In N,N-dimethyl-formamide at 23℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #3: With trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide at 23℃; for 1h; Schlenk technique; Inert atmosphere;

92%

: 1246610-74-1
2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane; water at 0 - 5℃; for 4h;	91%
With trifluoroacetic acid In methanol at 65℃; for 7h; Reagent/catalyst; Solvent;	83%
With citric acid for 2h; Reagent/catalyst; Reflux;	77.82%

: (R)-1-(3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)piperidine-3-carboxamide

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
With pyridine; [bis(acetoxy)iodo]benzene In water; isopropyl alcohol at 20℃; for 3h;	87%
With pyridine; bis-[(trifluoroacetoxy)iodo]benzene In water; isopropyl alcohol at 20℃; for 3h; Solvent; Hofmann Rearrangement;	87.2%

: 32315-10-9
bis(trichloromethyl) carbonate

: C22H31N5O3

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
In tetrahydrofuran at 45℃; for 5.5h;	86.5%

: 2-{6-[3(R)-Amino-piperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
With benzaldehyde In isopropyl alcohol at 60℃; under 675.068 Torr; for 24h;	82%

: 3-(R)-aminopiperidine dihydrochloride

: 4318-56-3
3-methyl-6-chlorouracil

: 22115-41-9
2-(bromomethyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Stage #1: 3-methyl-6-chlorouracil; 2-(bromomethyl)benzonitrile With dmap In acetonitrile at 80℃; for 6h; Green chemistry; Stage #2: 3-(R)-aminopiperidine dihydrochloride In acetonitrile for 8h; Reflux; Green chemistry;	73%

...Expand

: 865758-96-9
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile

: (R)-3-piperidinyl phthalimide hydrochloride

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Stage #1: 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile; 3-(R)-piperidinyl phthalimide hydrochloride With sodium hydrogencarbonate In methanol at 100℃; for 0.75h; Stage #2: With methanol; hydrazine hydrate for 4h; Reagent/catalyst; Temperature; Reflux; Further stages;	70%

: 865758-95-8
2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH; LiBr / dimethylformamide; tetrahydrofuran / 0.33 h / 20 °C 1.2: 72 percent / dimethylformamide; tetrahydrofuran / 0 - 35 °C 2.1: 2.7 g / NaHCO3; molecular sieves 4 Angstroem / ethanol / 4 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 50 - 60 °C 2: sodium hydrogencarbonate / methanol / 6 h / 65 - 70 °C / Molecular sieve View Scheme
Multi-step reaction with 2 steps 1.1: lithium bromide; sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: sodium hydrogencarbonate / isopropyl alcohol / 2 h / 100 °C / Molecular sieve View Scheme

: 22115-41-9
2-(bromomethyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide; dimethylsulfoxide / 0.5 h / 0 °C 1.2: LiBr / dimethylformamide; 1,2-dimethoxy-ethane / 0.25 h / 0 - 20 °C 1.3: 54 percent / dimethylformamide; dimethylsulfoxide / 0 - 20 °C 2.1: NaH; LiBr / dimethylformamide; tetrahydrofuran / 0.33 h / 20 °C 2.2: 72 percent / dimethylformamide; tetrahydrofuran / 0 - 35 °C 3.1: 2.7 g / NaHCO3; molecular sieves 4 Angstroem / ethanol / 4 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one; toluene / 70 - 80 °C 2: potassium carbonate / acetone / 50 - 60 °C 3: sodium hydrogencarbonate / methanol / 6 h / 65 - 70 °C / Molecular sieve View Scheme
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: lithium bromide; sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 2.2: 80 °C / Inert atmosphere 3.1: sodium hydrogencarbonate / isopropyl alcohol / 2 h / 100 °C / Molecular sieve View Scheme

: 4318-56-3
3-methyl-6-chlorouracil

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl acetamide / 50 - 100 °C 2: potassium carbonate / N,N-dimethyl acetamide / Heating 3: hydrogenchloride; ethanol / dichloromethane / -5 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl acetamide / 50 - 100 °C 2: potassium carbonate / N,N-dimethyl acetamide / Heating 3: hydrogenchloride; ethanol / dichloromethane / -5 - 25 °C View Scheme
Multi-step reaction with 2 steps 1: tributyl-amine / toluene / 5 h / 80 °C 2: triethylamine / isopropyl alcohol / 17 h / 65 °C View Scheme

: 612-13-5
2-cyanobenzyl chloride

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl acetamide / 50 - 100 °C 2: potassium carbonate / N,N-dimethyl acetamide / Heating 3: hydrogenchloride; ethanol / dichloromethane / -5 - 25 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 1 h / 60 °C 2: triethylamine / isopropyl alcohol; water / 13 h / 60 °C View Scheme

: 865758-96-9
2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl acetamide / Heating 2: hydrogenchloride; ethanol / dichloromethane / -5 - 25 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / methanol / 3 h / 100 °C / Molecular sieve 2: hydrazine hydrate / methanol / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / 6 h / 70 - 80 °C 2: hydrogenchloride / dichloromethane; ethanol / -5 - 20 °C View Scheme

: 2-({6-[(3R)-3-(5-methyl-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)piperidin-1-yl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.58 h / 25 - 30 °C 1.2: 25 - 55 °C 2.1: ethanolamine / 60 - 65 °C View Scheme

: 2-({3-methyl-6-[(3R)-3-(5-methyl-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)piperidin-1-yl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
With ethanolamine at 60 - 65℃;

: 127294-73-9
(R)-piperidin-3-ylamine

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid / toluene / 3 h / Reflux 2: sodium hydrogencarbonate / methanol / 3 h / 100 °C / Molecular sieve 3: hydrazine hydrate / methanol / 2 h / Reflux View Scheme

: ((R)-3-piperidinyl)-2,5-pyrrolidinedione

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / methanol / 3 h / 100 °C / Molecular sieve 2: hydrazine hydrate / methanol / 2 h / Reflux View Scheme

: C22H23N5O4

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 2h; Reflux;	197.7 g

: 7032-11-3
1,4,5,6-tetrahydropyridine-3-carboxamide

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen / methanol / 18 h / 65 °C / 8625.86 Torr / Autoclave 2: potassium carbonate / isopropyl alcohol; water / 23 h / 65 °C 3: pyridine; [bis(acetoxy)iodo]benzene / isopropyl alcohol; water / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: ditrifluoroacetato[(S)-(+)-4,12-bis(diphenylphosphino)-[2,2]-paracyclophane]ruthenium(II) complex; hydrogen; lithium bromide monohydrate / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave 2: potassium carbonate / isopropyl alcohol; water / 23 h / 65 °C 3: pyridine; [bis(acetoxy)iodo]benzene / isopropyl alcohol; water / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: ethanol / 20 °C 2: Ru-(CF3CO2)2{(S)-phanephos}; potassium bromide; hydrogen / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave 3: potassium carbonate / isopropyl alcohol; water / 18 h / 70 °C 4: bis-[(trifluoroacetoxy)iodo]benzene; pyridine / isopropyl alcohol; water / 3 h / 20 °C View Scheme

: 98-92-0
nicotinamide

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 5%-palladium/activated carbon; hydrogen / methanol / 20 h / 40 °C / 750.08 Torr / Autoclave 1.2: 3.5 h / 10 - 35 °C 2.1: ditrifluoroacetato[(RP,R′P)-1,1′-bis[(S)-α-(dimethylamino)benzyl]-2,2′-bis(diphenylphosphino)ferrocene]ruthenium(II); toluene-4-sulfonic acid; hydrogen; potassium bromide / isopropyl alcohol / 25 h / 5 - 50 °C / 6750.68 Torr / Autoclave 3.1: potassium carbonate / isopropyl alcohol; water / 23 h / 65 °C 4.1: pyridine; [bis(acetoxy)iodo]benzene / isopropyl alcohol; water / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 45 °C / 750.08 Torr / Autoclave 2: dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen / methanol / 18 h / 65 °C / 8625.86 Torr / Autoclave 3: potassium carbonate / isopropyl alcohol; water / 23 h / 65 °C 4: pyridine; [bis(acetoxy)iodo]benzene / isopropyl alcohol; water / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 45 °C / 750.08 Torr / Autoclave 2: ditrifluoroacetato[(S)-(+)-4,12-bis(diphenylphosphino)-[2,2]-paracyclophane]ruthenium(II) complex; hydrogen; lithium bromide monohydrate / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave 3: potassium carbonate / isopropyl alcohol; water / 23 h / 65 °C 4: pyridine; [bis(acetoxy)iodo]benzene / isopropyl alcohol; water / 3 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: hydrogen; palladium on carbon type-K / methanol / 21 h / 40 °C / 750.08 Torr / Autoclave 2: ethanol / 20 °C 3: Ru-(CF3CO2)2{(S)-phanephos}; potassium bromide; hydrogen / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave 4: potassium carbonate / isopropyl alcohol; water / 18 h / 70 °C 5: bis-[(trifluoroacetoxy)iodo]benzene; pyridine / isopropyl alcohol; water / 3 h / 20 °C View Scheme

: 309956-78-3
(R)-piperidin-3-ylcarbamic acid tert-butyl ester

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 75 °C 1.2: 75 °C 2.1: trifluoroacetic acid / dichloromethane / 25 °C View Scheme
Multi-step reaction with 2 steps 1.1: diethyl ether / 10 h / -15 - -10 °C 1.2: 8 h / 35 °C 2.1: tetrahydrofuran / 5.5 h / 45 °C View Scheme
Multi-step reaction with 3 steps 1.1: diethyl ether / 10 h / -15 - -10 °C 1.2: 8 h / 35 °C 2.1: sodium methylate / N,N-dimethyl-formamide / 0.25 h / 0 - 5 °C 2.2: 2 h / 50 °C 3.1: hydrogenchloride / dichloromethane; methanol; water / 4 h / 0 - 5 °C View Scheme

: 4318-56-3
3-methyl-6-chlorouracil

: 22115-41-9
2-(bromomethyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 23 °C / Schlenk technique; Inert atmosphere 1.2: 2 h / 65 °C / Schlenk technique; Inert atmosphere 2.1: palladium diacetate; (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate / N,N-dimethyl-formamide / 0.08 h / Schlenk technique; Inert atmosphere 2.2: 2 h / 23 °C / Schlenk technique; Inert atmosphere 2.3: 1 h / 23 °C / Schlenk technique; Inert atmosphere View Scheme

Yield

Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 23 °C / Schlenk technique; Inert atmosphere
1.2: 2 h / 65 °C / Schlenk technique; Inert atmosphere
2.1: palladium diacetate; (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate / N,N-dimethyl-formamide / 0.08 h / Schlenk technique; Inert atmosphere
2.2: 2 h / 23 °C / Schlenk technique; Inert atmosphere
2.3: 1 h / 23 °C / Schlenk technique; Inert atmosphere
View Scheme

: ethyl (R)-3-(3-Boc-aminopiperidin-1-yl)-3-oxopropanoate

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 6 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / methanol / 7 h / 65 °C View Scheme

: C22H31N5O3

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium methylate / N,N-dimethyl-formamide / 0.25 h / 0 - 5 °C 1.2: 2 h / 50 °C 2.1: hydrogenchloride / dichloromethane; methanol; water / 4 h / 0 - 5 °C View Scheme

: 344957-25-1
2-(aminomethyl)benzonitrile

: 850649-61-5
alogliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diethyl ether / 10 h / -15 - -10 °C 1.2: 8 h / 35 °C 2.1: tetrahydrofuran / 5.5 h / 45 °C View Scheme
Multi-step reaction with 3 steps 1.1: diethyl ether / 10 h / -15 - -10 °C 1.2: 8 h / 35 °C 2.1: sodium methylate / N,N-dimethyl-formamide / 0.25 h / 0 - 5 °C 2.2: 2 h / 50 °C 3.1: hydrogenchloride / dichloromethane; methanol; water / 4 h / 0 - 5 °C View Scheme

: 98-92-0
nicotinamide

A: 850649-61-5
alogliptin

B: C37H40N10O5

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogen; palladium on carbon type-K / methanol / 21 h / 40 °C / 750.08 Torr / Autoclave 2: ethanol / 20 °C 3: Ru-(CF3CO2)2{(S)-phanephos}; potassium bromide; hydrogen / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave 4: potassium carbonate / isopropyl alcohol; water / 18 h / 70 °C 5: bis-[(trifluoroacetoxy)iodo]benzene; sodium hydroxide / water; acetonitrile / 4 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: hydrogen; palladium on carbon type-K / methanol / 21 h / 40 °C / 750.08 Torr / Autoclave
2: ethanol / 20 °C
3: Ru-(CF3CO2)2{(S)-phanephos}; potassium bromide; hydrogen / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave
4: potassium carbonate / isopropyl alcohol; water / 18 h / 70 °C
5: bis-[(trifluoroacetoxy)iodo]benzene; sodium hydroxide / water; acetonitrile / 4 h / 0 - 20 °C
View Scheme

: (R)-1-(3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)piperidine-3-carboxamide

A: 850649-61-5
alogliptin

B: C37H40N10O5

Conditions

Conditions	Yield
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 20℃; for 1h; Reagent/catalyst;
With bis-[(trifluoroacetoxy)iodo]benzene; sodium hydroxide In water; acetonitrile at 0 - 20℃; for 4h;

: 7032-11-3
1,4,5,6-tetrahydropyridine-3-carboxamide

A: 850649-61-5
alogliptin

B: C37H40N10O5

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanol / 20 °C 2: Ru-(CF3CO2)2{(S)-phanephos}; potassium bromide; hydrogen / methanol / 15 h / 50 °C / 7500.75 Torr / Autoclave 3: potassium carbonate / isopropyl alcohol; water / 18 h / 70 °C 4: bis-[(trifluoroacetoxy)iodo]benzene; sodium hydroxide / water; acetonitrile / 4 h / 0 - 20 °C View Scheme

: 850649-61-5
alogliptin

: 65-85-0
benzoic acid

: Alogliptin benzoate

Conditions

Conditions	Yield
In ethanol at 50 - 80℃;	95.7%
In tetrahydrofuran for 1.5h; Reflux; Large scale;	94.68%
In ethanol at 60 - 70℃; for 0.166667h;	94.3%

: 850649-61-5
alogliptin

: C18H19N7O2

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	90%

: 850649-61-5
alogliptin

: 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]Methyl]-N-hydroxyamidinobenzene

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 85 - 90℃; for 20h;	80.9%

: 850649-61-5
alogliptin

: 2(13)CN(1-)*Zn(2+)

: C17(13)CH21N5O2

Conditions

Conditions	Yield
With C10H12O2NiC8H12-1,5-cyclo; triphenylborane; diphenyl(methyl)phosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;	58%

: 850649-61-5
alogliptin

: C18H23N5O3

Conditions

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol for 9h; Reagent/catalyst; Solvent; Reflux;	45.7%

: 850649-61-5
alogliptin

: C23H28N2O4

: C41H47N7O5

Conditions

Conditions	Yield
Stage #1: C23H28N2O4 With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0℃; for 0.666667h; Stage #2: alogliptin In dichloromethane at 20℃; for 6h;	30%

: 850649-61-5
alogliptin

: 2-{6-[3(R)-amino-piperidin-1-yl]-5-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

Conditions

Conditions	Yield
With thionyl chloride In chloroform at 100℃; for 0.5h;
With thionyl chloride In chloroform at 100℃; for 0.5h; Inert atmosphere;

: 850649-61-5
alogliptin

: 2-{6-[3(R)-amino-piperidin-1-yl]-5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 20℃; for 1h;

: 850649-61-5
alogliptin

: 104-15-4
toluene-4-sulfonic acid

: 1428858-00-7
2-{6-[3(R)-amino-piperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile p-toluenesulfonate

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; for 3h; Product distribution / selectivity; Inert atmosphere;

: 850649-61-5
alogliptin

: 1246610-75-2
Alogliptin hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 20℃; for 1.16667h; Inert atmosphere;

: 850649-61-5
alogliptin

: alogliptin sulfate

Conditions

Conditions	Yield
With sulfuric acid In ethanol for 3h; Solvent; Reflux;	1.3 g

: 850649-61-5
alogliptin

: alogliptin nitrate

Conditions

Conditions	Yield
With nitric acid In ethanol for 3h; Solvent; Reflux;	1.4 g

: 850649-61-5
alogliptin

: 65-85-0
benzoic acid

: alogliptin benzoate

Conditions

Conditions	Yield
In ethanol at 75 - 80℃; for 2h;	12 g

: 850649-61-5
alogliptin

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

: alogliptin fumarate

Conditions

Conditions	Yield
In ethanol for 3h; Solvent; Reflux;	1.7 g

: 850649-61-5
alogliptin

: 617-48-1
malic acid

: alogliptin malate

Conditions

Conditions	Yield
In ethanol for 3h; Solvent; Reflux;	1.8 g

: 850649-61-5
alogliptin

: 104-15-4
toluene-4-sulfonic acid

: alogliptin tosylate

Conditions

Conditions	Yield
In ethanol for 3h; Solvent; Reflux;	1.6 g

: 850649-61-5
alogliptin

: 144-62-7
oxalic acid

: alogliptin oxalate

Conditions

Conditions	Yield
In ethanol for 3h; Solvent; Reflux;	1.8 g

Alogliptin Specification

The Alogliptin with CAS registry number of 850649-61-5 is also known as UNII-JHC049LO86. The IUPAC name is 2-[[6-[(3R)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile. In addition, the formula is C₁₈H₂₁N₅O₂ and the molecular weight is 339.39. It is used as antidiabetic agent and is also an oral antihyperglycemic agent that is a selective inhibitor of the enzyme dipeptidyl peptidase-4 (DPP-4).

Physical properties about Alogliptin are: (1)ACD/LogP: 1.62; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 7; (7)#H bond donors: 2; (8)#Freely Rotating Bonds: 4; (9)Polar Surface Area: 93.67Å²; (10)Index of Refraction: 1.66; (11)Molar Refractivity: 93.332 cm³; (12)Molar Volume: 252.928 cm³; (13)Polarizability: 37×10^-24cm³; (14)Surface Tension: 70.912 dyne/cm; (15)Density: 1.342 g/cm³; (16)Flash Point: 267.826 °C; (17)Enthalpy of Vaporization: 79.195 kJ/mol; (18)Boiling Point: 519.238 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCCC(C3)N
2. Isomeric SMILES: CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCC[C@H](C3)N
3. InChI: InChI=1S/C18H21N5O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3/t15-/m1/s1
4. InChIKey: ZSBOMTDTBDDKMP-OAHLLOKOSA-N

Product Name

ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)

Synthetic route

Alogliptin Specification

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