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850649-61-5

Basic Information
CAS No.: 850649-61-5
Name: ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)
Article Data: 28
Molecular Structure:
Molecular Structure of 850649-61-5 (ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA))
Formula: C18H21N5O2
Molecular Weight: 339.397
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;
EINECS: 821-899-3
Density: 1.342 g/cm3
Boiling Point: 519.238 °C at 760 mmHg
Flash Point: 267.826 °C
Appearance: White powder
Safety: 24/25
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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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

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