Product Name

  • Name

    Repaglinide

  • EINECS 629-921-1
  • CAS No. 135062-02-1
  • Article Data16
  • CAS DataBase
  • Density 1.137 g/cm3
  • Solubility DMSO: 34 mg/mL
  • Melting Point 129-130.2 °C
  • Formula C27H36N2O4
  • Boiling Point 672.9 °C at 760 mmHg
  • Molecular Weight 452.594
  • Flash Point 360.8 °C
  • Transport Information
  • Appearance white to off-white solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 135062-02-1 (Repaglinide)
  • Hazard Symbols
  • Synonyms (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid;Novonorm;Prandin;
  • PSA 78.87000
  • LogP 5.67580

Synthetic route

(S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate
147770-06-7

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

(S)-repaglinide
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

C28H38N2O4

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile for 6h; Reflux;89.9%
C34H42N2O4

C34H42N2O4

(S)-repaglinide
135062-02-1

(S)-repaglinide

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

piperidine

trityl thiosemicarbazide resin

trityl thiosemicarbazide resin

(S)-repaglinide
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
2-(piperidin-1-yl)benzonitrile
72752-52-4

2-(piperidin-1-yl)benzonitrile

(S)-repaglinide
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
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

(S)-repaglinide
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
(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine
147769-93-5

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

(S)-repaglinide
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
(S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine
108157-52-4

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

(S)-repaglinide
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
3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine
147769-96-8

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

(S)-repaglinide
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
piperidine
110-89-4

piperidine

3.) methyl halide

3.) methyl halide

(S)-repaglinide
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
2-(piperidin-1-yl)benzonitrile
72752-52-4

2-(piperidin-1-yl)benzonitrile

cyclohexyl-CH2-MgX

cyclohexyl-CH2-MgX

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrahydrofuran; toluene / 3 h / Heating
2: 34 percent / toluene / 15 h / Ambient temperature
3: H2, NaOH, Et3N, Ti(OiPr)4 / Ru(OAc)2<(S)-BINAP> / methanol; CH2Cl2 / 170 h / 30 °C / 75006 Torr
4: aq. HCl / 5.5 h / Heating
5: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
6: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: tetrahydrofuran; toluene / 3 h / Heating
2: 4N aq. HCl / toluene; tetrahydrofuran / 20 °C
3: 63 percent / Et3N, TiCl4 / toluene / Ambient temperature
4: 76 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 72 h / 50 °C / 150012 Torr
5: H2, aq. HCl / 10 percent Pd/C / H2O / 5 h / 50 °C / 3750.3 Torr
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 7 steps
1: tetrahydrofuran; toluene / 3 h / Heating
2: 4N aq. HCl / toluene; tetrahydrofuran / 20 °C
3: Et3N, TiCl4 / toluene / Ambient temperature
4: 66 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 160 h / 160 °C / 150012 Torr
5: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr
6: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
7: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

2-chloro-benzaldehyde seqtrans-oxime

2-chloro-benzaldehyde seqtrans-oxime

(S)-repaglinide
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
2-hydroxy-p-toluic acid
50-85-1

2-hydroxy-p-toluic acid

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: K2CO3 / diethyl ether / 30 h / 150 °C
2: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
3: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
4: HCl / Heating
5: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
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: K2CO3 / diethyl ether / 30 h / 150 °C
2: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
3: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
4: HCl / Heating
5: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
6: 85 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 7 steps
1: K2CO3 / diethyl ether / 30 h / 150 °C
2: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
3: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
4: HCl / Heating
5: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
6: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
7: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
ethyl 2-ethoxy-4-methyl-benzoate
88709-17-5

ethyl 2-ethoxy-4-methyl-benzoate

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
2: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
3: HCl / Heating
4: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
5: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
6: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
2: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
3: HCl / Heating
4: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
5: 85 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 6 steps
1: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
2: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
3: HCl / Heating
4: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
5: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
6: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
2-(piperidin-1-yl)benzaldehyde
34595-26-1

2-(piperidin-1-yl)benzaldehyde

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Ambient temperature
2: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C
3: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr
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 5 steps
1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 20 - 65 °C
2.1: magnesium / tetrahydrofuran; dichloromethane / 1 h / -50 - 20 °C
3.1: hydrogenchloride / water / 20 °C
4.1: 4-methyl-morpholine; pivaloyl chloride / dichloromethane / 1 h / 0 - 5 °C
4.2: 15 h / 0 - 20 °C
5.1: sodium hydroxide / ethanol / 1 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 20 - 65 °C
2.1: magnesium / tetrahydrofuran; dichloromethane / 1 h / -50 - 20 °C
3.1: hydrogenchloride / water / 20 °C
4.1: 4-methyl-morpholine; pivaloyl chloride / dichloromethane / 1 h / 0 - 5 °C
4.2: 15 h / 0 - 20 °C
5.1: sodium hydroxide / ethanol / 1 h / 20 °C / Reflux
View Scheme
ethyl 4-bromomethyl-2-ethoxy-benzoate
110017-07-7

ethyl 4-bromomethyl-2-ethoxy-benzoate

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
2: HCl / Heating
3: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
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: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
2: HCl / Heating
3: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
4: 85 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
6: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
2: HCl / Heating
3: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
4: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
5: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
ethyl 4-cyanomethyl-2-ethoxy-benzoate
99470-01-6

ethyl 4-cyanomethyl-2-ethoxy-benzoate

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HCl / Heating
2: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
3: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: HCl / Heating
2: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
3: 85 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 4 steps
1: HCl / Heating
2: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
3: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
3-methyl-1-(2-piperidin-1-yl-phenyl)-butan-1-one
147770-03-4

3-methyl-1-(2-piperidin-1-yl-phenyl)-butan-1-one

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 63 percent / Et3N, TiCl4 / toluene / Ambient temperature
2: 76 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 72 h / 50 °C / 150012 Torr
3: H2, aq. HCl / 10 percent Pd/C / H2O / 5 h / 50 °C / 3750.3 Torr
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 5 steps
1: Et3N, TiCl4 / toluene / Ambient temperature
2: 66 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 160 h / 160 °C / 150012 Torr
3: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr
4: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
5: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
ethyl 4-(2-amino-2-oxoethyl)-2-ethoxybenzoate

ethyl 4-(2-amino-2-oxoethyl)-2-ethoxybenzoate

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 39 percent / aq. NaNO2, aq. HCl / 2 h / 35 °C
2: 29 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 4 steps
1: 39 percent / aq. NaNO2, aq. HCl / 2 h / 35 °C
2: 85 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 39 percent / aq. NaNO2, aq. HCl / 2 h / 35 °C
2: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid
99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
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 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 2 steps
1: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
2: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
ethyl 2-ethoxy-4-(2-ethoxy-2-oxoethyl)benzoate
332347-69-0

ethyl 2-ethoxy-4-(2-ethoxy-2-oxoethyl)benzoate

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
2: 29 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 4 steps
1: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
2: 85 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
2: 59 percent / N,N'-dicyclohexyl-carbodiimide / toluene / 2 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
N-acetyl-N-<(S)-3-methyl-1-(2-(1-piperidinyl)phenyl)-1-butyl>-amine
147769-98-0

N-acetyl-N-<(S)-3-methyl-1-(2-(1-piperidinyl)phenyl)-1-butyl>-amine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HCl / 5.5 h / Heating
2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
N-acetyl-N-<3-methyl-1-(2-(1-piperidinyl)phenyl)-1-(Z)-buten-1-yl>-amine
147769-97-9

N-acetyl-N-<3-methyl-1-(2-(1-piperidinyl)phenyl)-1-(Z)-buten-1-yl>-amine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2, NaOH, Et3N, Ti(OiPr)4 / Ru(OAc)2<(S)-BINAP> / methanol; CH2Cl2 / 170 h / 30 °C / 75006 Torr
2: aq. HCl / 5.5 h / Heating
3: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
<2-(1-piperidinyl)phenyl>-N-<(R')-1-phenethyl>-aldimine

<2-(1-piperidinyl)phenyl>-N-<(R')-1-phenethyl>-aldimine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C
2: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr
3: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
N-<(S)-3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>-N-<(R')-1-phenethyl>-amine
219922-07-3

N-<(S)-3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>-N-<(R')-1-phenethyl>-amine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr
2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
N-<(S)-3-methyl-1-<2-(1-pieridinyl)phenyl>butyl>-N-<(S')-1-phenethyl>-amine
147770-01-2

N-<(S)-3-methyl-1-<2-(1-pieridinyl)phenyl>butyl>-N-<(S')-1-phenethyl>-amine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / H2O / 5 h / 50 °C / 3750.3 Torr
2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
N-<(R)-3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>-N-<(R')-1-phenethyl>-amine
219921-97-8

N-<(R)-3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>-N-<(R')-1-phenethyl>-amine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr
2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
isobutyl-(2-piperidino-phenyl)-N-<(R')-1-phenethyl>-ketimine

isobutyl-(2-piperidino-phenyl)-N-<(R')-1-phenethyl>-ketimine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 66 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 160 h / 160 °C / 150012 Torr
2: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr
3: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
isobutyl-(2-piperidino-phenyl)-N-<(S')-1-phenethyl>-ketimine

isobutyl-(2-piperidino-phenyl)-N-<(S')-1-phenethyl>-ketimine

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / H2, Ti(O-iPr)4 / Raney-Ni / ethanol / 72 h / 50 °C / 150012 Torr
2: H2, aq. HCl / 10 percent Pd/C / H2O / 5 h / 50 °C / 3750.3 Torr
3: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
4: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
N-(2-piperidino-benzyl)-2-piperidino-benzaldimine

N-(2-piperidino-benzyl)-2-piperidino-benzaldimine

cycloheptyl-CH2-halide

cycloheptyl-CH2-halide

(S)-repaglinide
135062-02-1

(S)-repaglinide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) LDA / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, hexane, from -70 deg C to RT, overnight
2: HCl / 0.5 h / 0 °C
3: Ambient temperature
4: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C
5: H2, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr
6: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature
7: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C
View Scheme
1-deoxy-1-(methylamino)-D-glucitol
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

(S)-repaglinide
135062-02-1

(S)-repaglinide

C27H36N2O4*C7H17NO5

C27H36N2O4*C7H17NO5

Conditions
ConditionsYield
With 3-methyl-1-butyl acetate In chloroform at 65℃; Temperature;95.2%
berberine chloride
633-65-8

berberine chloride

(S)-repaglinide
135062-02-1

(S)-repaglinide

repaglinide berberine

repaglinide berberine

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 60 - 70℃; pH=7 - 8;91%
4-(1-hydroxyethyl)benzyl alcohol
80463-22-5

4-(1-hydroxyethyl)benzyl alcohol

(S)-repaglinide
135062-02-1

(S)-repaglinide

repaglinide 4-[1-(hydroxyethyl)]benzoate

repaglinide 4-[1-(hydroxyethyl)]benzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;90%
1-(3-(hydroxymethyl)phenyl)ethan-1-ol
1013027-15-0

1-(3-(hydroxymethyl)phenyl)ethan-1-ol

(S)-repaglinide
135062-02-1

(S)-repaglinide

repaglinide 3-[1-(hydroxyethyl)]benzoate

repaglinide 3-[1-(hydroxyethyl)]benzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;90%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

benzaldehyde
100-52-7

benzaldehyde

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(1-(4-cyanophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(1-(4-cyanophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;87%
...Expand
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

aniline
62-53-3

aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(1-(4-chlorophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(1-(4-chlorophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;85%
...Expand
(S)-repaglinide
135062-02-1

(S)-repaglinide

(S)-2-(3-ethoxy-4-formylphenyl)-N-(3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)acetamide

(S)-2-(3-ethoxy-4-formylphenyl)-N-(3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)acetamide

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane; dimethyl dicarbonate In acetonitrile at 20℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;84%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(2-(cyclohexylamino)-2-oxo-1-p-tolylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-m-tolylbenzamide

N-(2-(cyclohexylamino)-2-oxo-1-p-tolylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-m-tolylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;83%
...Expand
manganese(II) chloride tetrahydrate

manganese(II) chloride tetrahydrate

(S)-repaglinide
135062-02-1

(S)-repaglinide

C54H74MnN4O10*2H2O

C54H74MnN4O10*2H2O

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water for 2h; pH=9;82%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

aniline
62-53-3

aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(2-(cyclohexylamino)-2-oxo-1-p-tolylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(2-(cyclohexylamino)-2-oxo-1-p-tolylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;82%
...Expand
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

(S)-repaglinide
135062-02-1

(S)-repaglinide

diethyl (2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)phenyl)phosphonate

diethyl (2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)phenyl)phosphonate

Conditions
ConditionsYield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Inert atmosphere; Schlenk technique;80%
(S)-repaglinide
135062-02-1

(S)-repaglinide

C27H35(2)HN2O4

C27H35(2)HN2O4

Conditions
ConditionsYield
With 2C11H15O2(1-)*C10H14*Ru(2+); water-d2 In 1,4-dioxane at 100℃; for 16h;80%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-chloro-aniline
106-47-8

4-chloro-aniline

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(4-chlorophenyl)-N-(1-(4-cyanophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzamide

N-(4-chlorophenyl)-N-(1-(4-cyanophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;80%
...Expand
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;78%
...Expand
(S)-repaglinide
135062-02-1

(S)-repaglinide

phenol
108-95-2

phenol

(S)-phenyl 4-(2-((1-(2-cyclohexylphenyl)-3-methylbutyl)amino)-2-oxoethyl)-2-ethoxybenzoate

(S)-phenyl 4-(2-((1-(2-cyclohexylphenyl)-3-methylbutyl)amino)-2-oxoethyl)-2-ethoxybenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 50℃; Inert atmosphere;77%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

aniline
62-53-3

aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(2-(cyclohexylamino)-1-(4-nitrophenyl)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(2-(cyclohexylamino)-1-(4-nitrophenyl)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;77%
...Expand
(S)-1-(1-(4-isobutylphenyl)ethyl)cyclopropan-1-ol

(S)-1-(1-(4-isobutylphenyl)ethyl)cyclopropan-1-ol

(S)-repaglinide
135062-02-1

(S)-repaglinide

2-(7-ethoxy-3-((S)-3-(4-isobutylphenyl)-2-oxobutyl)-1-oxo-1,3-dihydroisobenzofuran-5-yl)-N-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)acetamide

2-(7-ethoxy-3-((S)-3-(4-isobutylphenyl)-2-oxobutyl)-1-oxo-1,3-dihydroisobenzofuran-5-yl)-N-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)acetamide

Conditions
ConditionsYield
With potassium phosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In acetonitrile at 80℃; for 24h; Sealed tube; Molecular sieve;77%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-chloro-aniline
106-47-8

4-chloro-aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(4-chlorophenyl)-N-(2-(cyclohexylamino)-2-oxo-1-p-tolylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzamide

N-(4-chlorophenyl)-N-(2-(cyclohexylamino)-2-oxo-1-p-tolylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;76%
...Expand
ethanethiol
75-08-1

ethanethiol

(S)-repaglinide
135062-02-1

(S)-repaglinide

repaglinide S-ethyl thioester

repaglinide S-ethyl thioester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere;75%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

aniline
62-53-3

aniline

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(1-(4-cyanophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(1-(4-cyanophenyl)-2-(cyclohexylamino)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;75%
...Expand
water
7732-18-5

water

zinc(II) chloride
7646-85-7

zinc(II) chloride

(S)-repaglinide
135062-02-1

(S)-repaglinide

C54H74N4O10Zn*H2O

C54H74N4O10Zn*H2O

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 3h; pH=8;74%
...Expand
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

aniline
62-53-3

aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(2-(cyclohexylamino)-1-(4-methoxyphenyl)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(2-(cyclohexylamino)-1-(4-methoxyphenyl)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;74%
...Expand
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

benzaldehyde
100-52-7

benzaldehyde

4-chloro-aniline
106-47-8

4-chloro-aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(4-chlorophenyl)-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzamide

N-(4-chlorophenyl)-N-(2-(cyclohexylamino)-2-oxo-1-phenylethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;73%
...Expand
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

aniline
62-53-3

aniline

(S)-repaglinide
135062-02-1

(S)-repaglinide

N-(2-(cyclohexylamino)-1-(3-nitrophenyl)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

N-(2-(cyclohexylamino)-1-(3-nitrophenyl)-2-oxoethyl)-2-ethoxy-4-(2-((S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)-N-phenylbenzamide

Conditions
ConditionsYield
In methanol at 20℃; for 6h; Ugi Condensation;72%
...Expand

Repaglinide Chemical Properties

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

Repaglinide 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).

Repaglinide 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.

Repaglinide Safety Profile

WGK Germany: 2
RTECS: 000000033825

Repaglinide 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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