Teneligliptin supplier | CasNO.760937-92-6

Name
Teneligliptin
EINECS
CAS No. 760937-92-6
Article Data6
CAS DataBase
Density 1.38
Solubility
Melting Point
Formula C22H30 N6 O S
Boiling Point 663.4±55.0 °C(Predicted)
Molecular Weight 426.586
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Thiazolidine,3-[[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]carbonyl]-(9CI); Teneligliptin
PSA 81.94000
LogP 1.83570

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 906093-30-9
1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine acetate

: 9H-fluoren-9-ylmethyl (2S)-4-oxo-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

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 2: piperidine / dichloromethane / 25 - 30 °C View Scheme

: 1-[2(S)-4-hydroxy-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidin-1-yl]ethanone

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; sulfur trioxide pyridine complex / dichloromethane / 2 h / 0 - 5 °C 2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 3: hydrogen bromide / water; isopropyl alcohol / 16 h / 80 - 85 °C View Scheme

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

: (5S)-1-acetyl-5-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidin-3-one

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 2: hydrogen bromide / water; isopropyl alcohol / 16 h / 80 - 85 °C View Scheme

: 19735-89-8
3-methyl-1-phenylpyrazolin-5(4H)-one

: 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

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 0.67 h / 10 - 30 °C 1.2: 1 h / 110 - 115 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 120 - 130 °C 3.1: sodium carbonate; toluene-4-sulfonic acid / methanol / 80 °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

Yield

Multi-step reaction with 5 steps
1.1: trichlorophosphate / 0.67 h / 10 - 30 °C
1.2: 1 h / 110 - 115 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 120 - 130 °C
3.1: sodium carbonate; toluene-4-sulfonic acid / methanol / 80 °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

: 947-95-5
5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole

: 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

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 120 - 130 °C 2: sodium carbonate; toluene-4-sulfonic acid / methanol / 80 °C 3: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 4: hydrogen bromide / water; isopropyl alcohol / 16 h / 80 - 85 °C View Scheme

: tert-butyl-4-(4-formyl-3-methyl-1-phenyl-1H-pyrazol-5-yl)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

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate; toluene-4-sulfonic acid / methanol / 80 °C 2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 3: hydrogen bromide / water; isopropyl alcohol / 16 h / 80 - 85 °C View Scheme

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

: 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

Conditions	Yield
With hydrogen bromide In water; isopropyl alcohol at 80 - 85℃; for 16h; Time;	0.360 g

: 100-63-0
phenylhydrazine

: 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

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 4 h / 110 - 115 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 5 °C 2.2: 0 - 30 °C 2.3: 2 h / 0 - 5 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 4.1: piperidine / dichloromethane / 25 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride / water / 4 h / 110 - 115 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 5 °C 2.2: 0 - 30 °C 3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 25 - 30 °C 3.2: 0 - 5 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 25 - 30 °C 5.1: piperidine / dichloromethane / 25 - 30 °C View Scheme

: 41327-15-5
5-bromo-3-methyl-1-phenyl-1H-pyrazole

: 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

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium t-butanolate / N,N-dimethyl-formamide 2: trifluoroacetic acid / methanol 3: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C 4: hydrogenchloride / 20 - 40 °C View Scheme

: 591-50-4
iodobenzene

: 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

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / acetonitrile 2: sodium t-butanolate / N,N-dimethyl-formamide 3: trifluoroacetic acid / methanol 4: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C 5: hydrogenchloride / 20 - 40 °C View Scheme

: 618-27-9
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

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydrogencarbonate / water; acetone / 20 °C 2: Jones reagent / acetone 3: formaldehyd; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / -10 - 20 °C 4: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C 5: hydrogenchloride / 20 - 40 °C View Scheme

: 87691-27-8
N-tert-butoxycarbonyl-L-cis-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

Conditions	Yield
Multi-step reaction with 4 steps 1: Jones reagent / acetone 2: formaldehyd; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / -10 - 20 °C 3: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C 4: hydrogenchloride / 20 - 40 °C View Scheme

: 84348-37-8
N-tert-butoxycarbonyl-4-oxo-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

Conditions	Yield
Multi-step reaction with 3 steps 1: formaldehyd; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / -10 - 20 °C 2: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C 3: hydrogenchloride / 20 - 40 °C View Scheme

: 401564-36-1
(2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 20 - 40 °C 2: hydrogenchloride / 20 - 40 °C View Scheme

: teneligliptin dibenzoyl-L-tartaric acid

: 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

Conditions	Yield
With sodium carbonate In dichloromethane; water for 0.5h;

: 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

: teneligliptin hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide at 30 - 50℃;	96%

: 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

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine sulfate

Conditions

Conditions	Yield
With sulfuric acid In tetrahydrofuran; water at 20℃; for 0.5h;	94%

: 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

: 35963-20-3
(R)-10-camphorsulfonic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine di-(-)-camphorsulfonate

Conditions

Conditions	Yield
In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 1h;	91%

: 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

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-yl-carbonyl}thiazolidine hemipentahydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In ethanol at 20℃; for 2h; Reflux;	90%

: 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

: 149-91-7
3,4,5-trihydroxybenzoic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine gallate

Conditions

Conditions	Yield
In isopropyl alcohol at 20℃; for 1h;	85%

: 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

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

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine ditosylate

Conditions

Conditions	Yield
In isopropyl alcohol at 20℃; for 1.5h;	82%

: 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

: 98-11-3
benzenesulfonic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine dibesylate

Conditions

Conditions	Yield
In isopropyl alcohol at 20℃; for 1h;	80%

: 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

: 87-69-4
L-Tartaric acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine ditartrate

Conditions

Conditions	Yield
In isopropyl alcohol at 20℃; for 3h;	78%

: 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

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

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine difumarate

Conditions

Conditions	Yield
In ethanol at 0 - 20℃; for 2h;	77%

: 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

: 85-47-2
1-naphthalenesulfonic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine dinaphthalene-1-sulfonate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	75%

: 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

: 120-18-3
naphthalene-2-sulfonate

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine dinaphthalene-2-sulfonate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 12h;	74%

: 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

: 75-75-2
methanesulfonic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine trimesylate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 1.5h;	72%

: 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

: 75-75-2
methanesulfonic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine dimesylate

Conditions

Conditions	Yield
In isopropyl alcohol at 20℃; for 2h;	72%

: 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

: 110-16-7
maleic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine dimaleate

Conditions

Conditions	Yield
In ethanol at 20℃; for 1h;	71%

: 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

: 3144-16-9
(1S)-10-camphorsulfonic acid

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine di-(+)-camphorsulfonate

Conditions

Conditions	Yield
In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 5h;	58%

: 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

: 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; ethyl acetate at 20℃; for 1h;	48%

: 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

: Teneligliptin hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In ethanol; water at 20℃; for 2h; Product distribution / selectivity; Heating / reflux;
With hydrogen bromide In methanol; water; tert-butyl alcohol at 70 - 75℃; for 1h;	8 g
With hydrogen bromide In ethanol; water at 80℃; for 0.5h;	80 mg

Teneligliptin Chemical Properties

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

Teneligliptin 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 .

Product Name

Teneligliptin

Synthetic route

Teneligliptin Chemical Properties

Teneligliptin Specification

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