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135062-02-1

Basic Information
CAS No.: 135062-02-1
Name: Repaglinide
Article Data: 16
Cas Database
Molecular Structure:
Molecular Structure of 135062-02-1 (Repaglinide)
Formula: C27H36N2O4
Molecular Weight: 452.594
Synonyms: (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid;Novonorm;Prandin;
EINECS: 629-921-1
Density: 1.137 g/cm3
Melting Point: 129-130.2 °C
Boiling Point: 672.9 °C at 760 mmHg
Flash Point: 360.8 °C
Solubility: DMSO: 34 mg/mL
Appearance: white to off-white solid
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 78.87000
LogP: 5.67580
Synthetic route
147770-06-7

(S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
With ethanol; water; sodium hydroxide Reflux;96%
With sodium hydroxide In ethanol at 60℃; for 4h;92%
With methanol; sodium hydroxide for 3h; Reflux;87.6%

C28H38N2O4

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile for 6h; Reflux;89.9%

C34H42N2O4

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
With ethanol; sodium hydroxide for 5h; Reflux;85.1%
110-89-4

piperidine

trityl thiosemicarbazide resin

trityl thiosemicarbazide resin

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 64.5 g / 6 h / 220 - 225 °C
2.1: Mg; I2 / tetrahydrofuran / 1 h / 60 - 65 °C / Heating
2.2: toluene; tetrahydrofuran / 14 h / 98 - 102 °C
3.1: 68.9 g / NaBH4 / methanol / 10 - 15 °C
4.1: N-acetyl-L-glutamic acid / acetone
5.1: 80 percent / N,N-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
6.1: aq. NaOH / propan-2-ol / 60 - 65 °C
View Scheme
72752-52-4

2-(piperidin-1-yl)benzonitrile

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Mg; I2 / tetrahydrofuran / 1 h / 60 - 65 °C / Heating
1.2: toluene; tetrahydrofuran / 14 h / 98 - 102 °C
2.1: 68.9 g / NaBH4 / methanol / 10 - 15 °C
3.1: N-acetyl-L-glutamic acid / acetone
4.1: 80 percent / N,N-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
5.1: aq. NaOH / propan-2-ol / 60 - 65 °C
View Scheme
873-32-5

2-Chlorobenzonitrile

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 64.5 g / 6 h / 220 - 225 °C
2.1: Mg; I2 / tetrahydrofuran / 1 h / 60 - 65 °C / Heating
2.2: toluene; tetrahydrofuran / 14 h / 98 - 102 °C
3.1: 68.9 g / NaBH4 / methanol / 10 - 15 °C
4.1: N-acetyl-L-glutamic acid / acetone
5.1: 80 percent / N,N-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
6.1: aq. NaOH / propan-2-ol / 60 - 65 °C
View Scheme
147769-93-5

(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / N,N-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
2: aq. NaOH / propan-2-ol / 60 - 65 °C
View Scheme
Multi-step reaction with 2 steps
1: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
2: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 4-methyl-morpholine; pivaloyl chloride / dichloromethane / 1 h / 0 - 5 °C
1.2: 15 h / 0 - 20 °C
2.1: sodium hydroxide / ethanol / 1 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: tetramethylorthosilicate / toluene / 10 h / Inert atmosphere; Reflux
2: sodium hydroxide; ethanol / 5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: tetramethylorthosilicate / toluene / 11 h / Inert atmosphere; Reflux
2: sodium hydroxide; methanol / 3 h / Reflux
View Scheme
108157-52-4

(S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-acetyl-L-glutamic acid / acetone
2: 80 percent / N,N-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
3: aq. NaOH / propan-2-ol / 60 - 65 °C
View Scheme
Multi-step reaction with 3 steps
1: 85 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
147769-96-8

3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 68.9 g / NaBH4 / methanol / 10 - 15 °C
2: N-acetyl-L-glutamic acid / acetone
3: 80 percent / N,N-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
4: aq. NaOH / propan-2-ol / 60 - 65 °C
View Scheme
Multi-step reaction with 5 steps
1: 34 percent / toluene / 15 h / Ambient temperature
2: H2, NaOH, Et3N, Ti(OiPr)4 / Ru(OAc)2<(S)-BINAP> / methanol; CH2Cl2 / 170 h / 30 °C / 75006 Torr
3: aq. HCl / 5.5 h / Heating
4: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
5: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1: 4N aq. HCl / toluene; tetrahydrofuran / 20 °C
2: 63 percent / Et3N, TiCl4 / toluene / Ambient temperature
3: 76 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 72 h / 50 °C / 150012 Torr
4: H2, aq. HCl / 10 percent Pd/C / H2O / 5 h / 50 °C / 3750.3 Torr
5: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
6: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
110-89-4

piperidine

3.) methyl halide

3.) methyl halide

135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 °C
2: tetrahydrofuran; toluene / 3 h / Heating
3: 34 percent / toluene / 15 h / Ambient temperature
4: H2, NaOH, Et3N, Ti(OiPr)4 / Ru(OAc)2<(S)-BINAP> / methanol; CH2Cl2 / 170 h / 30 °C / 75006 Torr
5: aq. HCl / 5.5 h / Heating
6: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
7: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 8 steps
1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 °C
2: tetrahydrofuran; toluene / 3 h / Heating
3: 4N aq. HCl / toluene; tetrahydrofuran / 20 °C
4: 63 percent / Et3N, TiCl4 / toluene / Ambient temperature
5: 76 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 72 h / 50 °C / 150012 Torr
6: H2, aq. HCl / 10 percent Pd/C / H2O / 5 h / 50 °C / 3750.3 Torr
7: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
8: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 8 steps
1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 °C
2: tetrahydrofuran; toluene / 3 h / Heating
3: 4N aq. HCl / toluene; tetrahydrofuran / 20 °C
4: Et3N, TiCl4 / toluene / Ambient temperature
5: 66 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 160 h / 160 °C / 150012 Torr
6: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr
7: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
8: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
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    135062-02-1

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Chemistry

CAS NO: 135062-02-1
Molecular Formula: C27H36N2O4
Molecular Weight: 452.585740 g/mol
Index of Refraction: 1.567
Surface Tension: 47 dyne/cm
Density: 1.137 g/cm3
Flash Point: 360.8 °C
Enthalpy of Vaporization: 103.84 kJ/mol
Boiling Point: 672.9 °C at 760 mmHg
Vapour Pressure: 5E-19 mmHg at 25°C
Melting Point: 129-130.2 °C
Storage temp: 2-8°C
Solubility DMSO: 34 mg/mL
Appearance: White to off-white solid
Molecular Structure: 
IUPAC Name: 2-Ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
Synonyms of Repaglinide (CAS NO.135062-02-1) : (+)-2-Ethoxy-alpha-(((S)-alpha-isobutyl-o-piperidinobenzyl)carbamoyl)-p-toluic acid ; (S)-2-Ethoxy-4-(2-((methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-benzoic acid ; Prandin ; Repaglinida ; Repaglinidum ; Benzoic acid, 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-, (S)-
Product Categories: Pharmaceutical material and intermeidates;Active Pharmaceutical Ingredients;Chiral Reagents;Amino Acids 13C, 2H, 15N;Chemical Impurities;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Amino Acids & Derivatives

History

The drug was the first of the meglitinide class, which was later licensed by Boehringer to Novo Nordisk, which filed an Investigational New Drug application for the compound with the Food and Drug Administration (FDA) in April 1992. Novo Nordisk filed its New Drug Application (NDA) for Prandin in July 1997 and it was quickly approved, gaining FDA approval in December 1997. . Repaglinide (CAS NO.135062-02-1) was branded Prandin because its quick onset and short duration of action concentrates its effect around meal time (the prandium was the Roman meal which is comparable to the modern lunch).

Uses

 Repaglinide (CAS NO.135062-02-1) is used for the treatment of type II diabetes. It belongs to the meglitinide class of blood glucose-lowering drugs.

Safety Profile

WGK Germany: 2
RTECS: 000000033825

Specification

 Repaglinide (CAS NO.135062-02-1) should not be administered concomitantly with gemfibrozil, clarithromycin or azole antifungals such as itraconazole or ketoconazole.Administration of both repaglinide and one or more of these drugs results in an increase in plasma concentration of repaglinide and may lead to hypoglycemia.

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