Water → 6-(((dimethylamino)ethyl)amino)-3-(pivaloyloxy)-7H-indeno[2,1-c]quinoline-7-on

HRID 377595Notes

Reaction equation

HRID 377595 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:17](=[O:24])[C:18]3[C:23]([C:15]=2[C:14]2[C:9](=[CH:10][C:11]([OH:25])=[CH:12][CH:13]=2)[N:8]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:3].[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:3][N:2]([CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:17](=[O:24])[C:18]3[C:23]([C:15]=2[C:14]2[C:9](=[CH:10][C:11]([O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:12][CH:13]=2)[N:8]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 135413533TAS-103 free base

Product 1

HCID 223716606-(((dimethylamino)ethyl)amino)-3-(pivaloyloxy)-7H-indeno[2,1-c]quinoline-7-onYield 83.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 3 (100 mg, 0.3 mmol) in dichloromethane (10 ml) was added 4-dimethylaminopyridine (100 mg, 0.8 mmol) and pivaloyl chloride (37 μl, 0.3 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water to wash the organic layer, which was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)) and crystallized from hexane to give 105 mg (yield: 80.0%) of title compound. The physicochemical properties thereof are shown in table 1.

Workup

  1. washto wash the organic layer, which
  2. dry with materialwas dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)) and
  5. customcrystallized from hexane

Sources & evidence

ORD record
ord-9f4780708aff4fbfa89d6a993c861ecd
Source dataset
uspto-grants-2000_02
Patent number
US06028079

Reaction notes

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