CAS No.135062-02-1,Repaglinide Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	135062-02-1
Name:	Repaglinide
Article Data:	16

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
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

Conditions	Yield
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

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

: C34H42N2O4

: 135062-02-1
(S)-repaglinide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Raw Materials

50-85-1

873-32-5

110-89-4

147770-10-3

Total:240 Page 1 of 7 1 2 3 4 5 6 …7 Next>>

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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.