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760937-92-6

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Basic Information
CAS No.: 760937-92-6
Name: Teneligliptin
Article Data: 6
Molecular Structure:
Molecular Structure of 760937-92-6 (Teneligliptin)
Formula: C22H30 N6 O S
Molecular Weight: 426.586
Synonyms: Thiazolidine,3-[[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]carbonyl]-(9CI); Teneligliptin
Density: 1.38
Boiling Point: 663.4±55.0 °C(Predicted)
PSA: 81.94000
LogP: 1.83570
Related products
Synthetic route
401566-80-1

tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Stage #1: tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 19h;
Stage #2: With sodium hydrogencarbonate In water		93%
With ethyl acetate; trifluoroacetic acid In dichloromethane at 20℃; for 19h;93%
With hydrogenchloride at 20 - 40℃; Reagent/catalyst;
401566-77-6

tert-butyl 4-(3-oxobutanoyl)piperazine-1-carboxylate

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: methanesulfonic acid / ethanol / 14 h / 20 °C
1.2: 20 h / 20 °C / pH 3
2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C
3.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 13 h / 20 °C
4.1: ethyl acetate; trifluoroacetic acid / dichloromethane / 19 h / 20 °C
View Scheme

1-tert-butoxycarbonyl-4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 13 h / 20 °C
3: ethyl acetate; trifluoroacetic acid / dichloromethane / 19 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: trifluoroacetic acid / dichloromethane / 1.5 h / 25 - 30 °C
1.2: 0 - 5 °C
2.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
3.1: piperidine / dichloromethane / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / methanol
2: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C
3: hydrogenchloride / 20 - 40 °C
View Scheme

1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 13 h / 20 °C
2: ethyl acetate; trifluoroacetic acid / dichloromethane / 19 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C
2: hydrogenchloride / 20 - 40 °C
View Scheme
1131-18-6

1-Phenyl-3-methyl-5-aminopyrazole

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 5 °C
1.2: 0 - 30 °C
1.3: 2 h / 0 - 5 °C
2.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
3.1: piperidine / dichloromethane / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 5 °C
1.2: 0 - 30 °C
2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 25 - 30 °C
2.2: 0 - 5 °C
3.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
4.1: piperidine / dichloromethane / 25 - 30 °C
View Scheme

C37H40N6O3S

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
With piperidine In dichloromethane at 25 - 30℃;10.5 g
51-35-4

4R-4-hydroxyproline

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: water / 3 h / 40 - 50 °C
2.1: benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 5 °C
2.2: 24 h / 25 - 30 °C
3.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane / 2 h / 0 - 5 °C
4.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
5.1: hydrogen bromide / water; isopropyl alcohol / 16 h / 80 - 85 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydrogencarbonate / water; tetrahydrofuran / 25 - 30 °C
2.1: benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 5 °C
2.2: 24 h / 25 - 30 °C
3.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 5 °C
4.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
5.1: piperidine / dichloromethane / 25 - 30 °C
View Scheme
33996-33-7

oxaceprol

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 5 °C
1.2: 24 h / 25 - 30 °C
2.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane / 2 h / 0 - 5 °C
3.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
4.1: hydrogen bromide / water; isopropyl alcohol / 16 h / 80 - 85 °C
View Scheme
88050-17-3

N-Fmoc-trans-4-Hydroxy-L-Proline

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 5 °C
1.2: 24 h / 25 - 30 °C
2.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 5 °C
3.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
4.1: piperidine / dichloromethane / 25 - 30 °C
View Scheme

3-[(2S,4R)-1-fluorenylmethoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]1,3-thiazolidine

760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 5 °C
2: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C
3: piperidine / dichloromethane / 25 - 30 °C
View Scheme
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Chemistry

Molecule structure of Teneligliptin (CAS NO.760937-92-6):

IUPAC Name: [(2S,4S)-4-[4-(5-methyl-2-phenylpyrazol-3-yl)piperazin-1-yl]pyrrolidin-2-yl]-(1,3-thiazolidin-3-yl)methanone 
Molecular Weight: 426.5782 [g/mol]
Molecular Formula: C22H30N6OS 
Density: 1.38 g/cm3
XLogP3-AA: 2.4
H-Bond Donor: 1
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Exact Mass: 426.22018
MonoIsotopic Mass: 426.22018
Topological Polar Surface Area: 56.6
Heavy Atom Count: 30
Canonical SMILES: CC1=NN(C(=C1)N2CCN(CC2)C3CC(NC3)C(=O)N4CCSC4)C5=CC=CC=C5
Isomeric SMILES: CC1=NN(C(=C1)N2CCN(CC2)[C@H]3C[C@H](NC3)C(=O)N4CCSC4)C5=CC=CC=C5
InChI: InChI=1S/C22H30N6OS/c1-17-13-21(28(24-17)18-5-3-2-4-6-18)26-9-7-25(8-10-26)19-14-20(23-15-19)22(29)27-11-12-30-16-27/h2-6,13,19-20,23H,7-12,14-16H2,1H3/t19-,20-/m0/s1
InChIKey: WGRQANOPCQRCME-PMACEKPBSA-N

Specification

 Teneligliptin (CAS NO.760937-92-6) is also named as 3-[[(2S,4S)-4-[4-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]carbonyl]thiazolidine .