We can provide high quality,cheap price,spot supply and good service. If you have any questions,pls do not hesitate to contact us. Hangzhou Hysen pharma CO.,LTD. is a professional Pharmaceutical company. We are specialized in manufacturing and
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inquiryDayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
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inquiryUnique advantages for Repaglinide Cas 135062-02-1 Guaranteed the purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:Powder Storage:2-8°C Package:20g/bag, 1kg/foil bag or as you require Applic
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inquiryhigh quality Appearance:White or off-white Solid Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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Production Name:Repaglinide CAS NO:135062-02-1 EINECS No.:N/A Molecular Formula:C27H36N2O4 Molecular Weight:452.59 Density: 1.137g/cm3 Melting Point(℃): 129-130℃ Boiling Point(℃): 672.9°C at 760 mmHg Flash Point(℃): 360.8
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Cas:135062-02-1
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Cas:135062-02-1
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inquiryProduct Name: Repaglinide CAS: 135062-02-1 MF: C27H36N2O4 MW: 452.59 EINECS: 629-921-1 Mol File: 135062-02-1.mol Repaglinide Structure Repaglinide Chemical Properties Melting point 129-130.2 °C alpha D20 +6.97° (c
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Cas:135062-02-1
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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Cas:135062-02-1
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Type:Lab/Research institutions
inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
(S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate
(S)-repaglinide
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% |
(S)-repaglinide
Conditions | Yield |
---|---|
With potassium hydroxide In acetonitrile for 6h; Reflux; | 89.9% |
(S)-repaglinide
Conditions | Yield |
---|---|
With ethanol; sodium hydroxide for 5h; Reflux; | 85.1% |
piperidine
(S)-repaglinide
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 |
2-(piperidin-1-yl)benzonitrile
(S)-repaglinide
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 |
2-Chlorobenzonitrile
(S)-repaglinide
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 |
(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine
(S)-repaglinide
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 |
(S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine
(S)-repaglinide
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 |
3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine
(S)-repaglinide
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 |
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 |
2-(piperidin-1-yl)benzonitrile
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
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 |
2-hydroxy-p-toluic acid
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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 |
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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 |
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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
(S)-repaglinide
Conditions | Yield |
---|---|
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 |
(S)-repaglinide
Conditions | Yield |
---|---|
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 |
(S)-repaglinide
Conditions | Yield |
---|---|
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 |
(S)-repaglinide
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With 3-methyl-1-butyl acetate In chloroform at 65℃; Temperature; | 95.2% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 60 - 70℃; pH=7 - 8; | 91% |
4-(1-hydroxyethyl)benzyl alcohol
(S)-repaglinide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 90% |
1-(3-(hydroxymethyl)phenyl)ethan-1-ol
(S)-repaglinide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 90% |
Cyclohexyl isocyanide
benzaldehyde
1-amino-3-methylbenzene
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 87% |
Cyclohexyl isocyanide
4-chlorobenzaldehyde
aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 85% |
(S)-repaglinide
Conditions | Yield |
---|---|
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
4-methyl-benzaldehyde
1-amino-3-methylbenzene
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 83% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 2h; pH=9; | 82% |
Cyclohexyl isocyanide
4-methyl-benzaldehyde
aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 82% |
phosphonic acid diethyl ester
(S)-repaglinide
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With 2C11H15O2(1-)*C10H14*Ru(2+); water-d2 In 1,4-dioxane at 100℃; for 16h; | 80% |
Cyclohexyl isocyanide
4-chloro-aniline
4-cyanobenzaldehyde
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 80% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 78% |
(S)-repaglinide
phenol
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 50℃; Inert atmosphere; | 77% |
Cyclohexyl isocyanide
4-nitrobenzaldehdye
aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 77% |
(S)-repaglinide
Conditions | Yield |
---|---|
With potassium phosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In acetonitrile at 80℃; for 24h; Sealed tube; Molecular sieve; | 77% |
Cyclohexyl isocyanide
4-methyl-benzaldehyde
4-chloro-aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 76% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere; | 75% |
Cyclohexyl isocyanide
aniline
4-cyanobenzaldehyde
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 75% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 3h; pH=8; | 74% |
Cyclohexyl isocyanide
4-methoxy-benzaldehyde
aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 74% |
Cyclohexyl isocyanide
benzaldehyde
4-chloro-aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 73% |
Cyclohexyl isocyanide
3-nitro-benzaldehyde
aniline
(S)-repaglinide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi Condensation; | 72% |
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