Tetrahydrofuran → HCID 67087961, compound

HRID 570592Notes

Reaction equation

HRID 570592 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC1C=CC=CC=1)=O)[C:6](=[O:20])[C:5]2([C:31]1[C:32]([O:37][CH2:38][CH3:39])=[N:33][CH:34]=[CH:35][CH:36]=1)[O:21][C:22]([O:24]C1C=CC=CC=1)=O.[CH3:40][N:41]1[CH2:46][CH2:45][CH:44]([N:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH2:43][CH2:42]1.C1COCC1>ClCCl>[CH3:40][N:41]1[CH2:42][CH2:43][CH:44]([N:47]2[CH2:52][CH2:51][N:50]([C:22]([O:21][C:5]3([C:31]4[C:32]([O:37][CH2:38][CH3:39])=[N:33][CH:34]=[CH:35][CH:36]=4)[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[NH:7][C:6]3=[O:20])=[O:24])[CH2:49][CH2:48]2)[CH2:45][CH2:46]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 67088001HCID 67088001, compound

Product 1

HCID 67087961HCID 67087961, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.29 g (2.37 mmol) of phenyl 5-chloro-3-(2-ethoxypyridin-3-yl)-2-oxo-3-phenoxycarbonyloxy-2,3-dihydroindole-1-carboxylate, 1.73 g (9.46 mmol) of 1-(1-methylpiperidin-4-yl)piperazine and 10 ml of dry THF was stirred at room temperature for 72 hours. The reaction mixture was diluted with dichloromethane and extracted with water and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was stirred with diethyl ether. 963 mg of the title compound were obtained as a white solid.

Workup

  1. extractionextracted with water and saturated sodium chloride solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. stirringThe residue was stirred with diethyl ether

Sources & evidence

ORD record
ord-b68aaab0e1374483b7539d2446788132
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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