ChemicalBook CAS DataBase List 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile ethanedioate

1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile ethanedioate synthesis

4synthesis methods

Product Name:1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile ethanedioate
CAS Number:885340-12-5
Molecular formula:C34H36F3N3O8
Molecular Weight:671.67

885340-11-4 Synthesis

1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

885340-11-4
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144-62-7 Synthesis

144-62-7
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1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile ethanedioate

885340-12-5
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Yield: 85%

Reaction Conditions:

in water;isopropyl alcoholLarge scale;

Steps:

1.3 Step 3: Preparation of benzoic acid-R-3- [7-cyano-5- (2- {2- [2- (2,2,2-trifluoro- ethoxy) -phenoxy] Amino} -propyl) -2,3-dihydro-indol-1-yl] -propyl oxalate
1. The second step directly to the system of ethanol 1.43L,Add about 0.14Kg sodium borohydride in portions and continue stirring;2. Dianban monitoring, the reaction is completed, slowly adding water 10Kg;3. Stirring, standing still, the aqueous phase was extracted once with 3 L of dichloromethane, the combined organic phase;The organic phase was washed with saturated saline, sodium carbonate solution and dried over anhydrous sodium sulfate.5. Concentrate the solvent to give 1.93 Kg of an oil as an oilBenzoic acid -R-3- [7-Cyano-5- (2- {2- [2- (2,2,2- trifluoro-ethoxy) -phenoxy] -ethylamino} -propyl ) -2,3-dihydro-indol-1-yl] -Propyl ester,Add 5.7L isopropanol dissolved, then add 0.57 liters of water and anhydrous oxalic acid 0.26Kg, precipitated a large amount of solid recrystallization, suction filtered to give a white solid, dried, about 1.57Kg white solid, benzoic acid-R-3- [7 (2- {2- [2- (2,2,2-trifluoro-ethoxy) -phenoxy] -ethylamino} -propyl) -2,3-dihydro- Indol-1-yl] -propyl oxalate.

References:

Beijing Tiantaihenghua Pharmaceutical Co., Ltd.;Li Xueqin;Liu Wenhui CN106995399, 2017, A Location in patent:Paragraph 0053-0063; 0088-0098; 0123-0133; 0158-0168

239463-72-0 Synthesis

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-carbonitrile-1H-indole

239463-72-0
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144-62-7 Synthesis

144-62-7
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160969-03-9 Synthesis

2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethyl methanesulfonate

160969-03-9
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$6.00/250mg

885340-12-5
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References

239463-85-5 Synthesis

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

239463-85-5
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885340-12-5
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References

239463-72-0 Synthesis

239463-72-0
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885340-12-5
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References