Diethyl (ethoxymethylene)malonate → HCID 66653275, compound

HRID 535463Notes

Reaction equation

HRID 535463 reaction equation
CCO[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[N:33]3[C:28]([CH:29]=[CH:30][CH:31]=[CH:32]3)=[C:27]([O:34][CH3:35])[C:26]=2[CH3:36])=[O:24])=[CH:19][CH:18]=1.C(OC(C)C)(C)C.CCCCC>C1(C)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:35][O:34][C:27]1[C:26]([CH3:36])=[C:25]([C:23]([C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]3=[O:13])=[O:24])[N:33]2[C:28]=1[CH:29]=[CH:30][CH:31]=[CH:32]2

Participants

7

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7914Diisopropyl EtherHCID 8003PentaneHCID 66653091HCID 66653091, compound

Product 1

HCID 66653275HCID 66653275, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

0.36 ml of diethyl ethoxymethylene malonate is added, under an inert atmosphere at ambient temperature, to 0.4 g (1.43 mmol) of (4-aminophenyl)(1-methoxy-2-methylindolizin-3-yl)methanone in 6 ml of toluene. The reaction medium is heated at 110° C. for 1 h 45 and then concentrated under reduced pressure. The residue obtained is dissolved in 8.2 ml of diphenyl ether and then heated at 230° C. for 1 h 20. After the addition of diisopropyl ether and pentane at ambient temperature, the precipitate formed is filtered off and rinsed with pentane. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 142 mg of a yellow powder are obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. temperatureheated at 230° C. for 1 h 20
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with pentane
  7. customThe residue obtained
  8. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-a48e68fef1d84b809624b224352e9f8f
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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