2,5-Dimethoxytetrahydrofuran → HCID 178517327, compound

HRID 1007463Notes

Reaction equation

HRID 1007463 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12](/[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:22][CH:21]=3)\[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.CO[CH:35]1[CH2:39][CH2:38][CH:37](OC)O1>C(O)(=O)C>[N:27]1([CH2:26][C:23]2[CH:24]=[CH:25][C:20]([NH:19]/[C:12](=[C:6]3\[C:7](=[O:11])[NH:8][C:9]4[C:5]\3=[CH:4][CH:3]=[C:2]([N:1]3[CH:35]=[CH:39][CH:38]=[CH:37]3)[CH:10]=4)/[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:21][CH:22]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 178507260HCID 178507260, compound

Product 1

HCID 178517327HCID 178517327, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.5 g of 6-amino-3-(Z)-{1-[4-(piperidin-1-yl-methyl)-anilino]-1-phenyl-methylidene}-2-indolinone are dissolved in 20 ml of glacial acetic acid and 0.2 ml of 2,5-dimethoxytetrahydrofuran are added. The mixture is refluxed for 1 hour, concentrated by evaporation and the residue is taken up in 20 ml of water. After another 2 hours' stirring the mixture is made basic with 1N sodium hydroxide solution, the aqueous phase is extracted with methylene chloride and the organic phase is dried over sodium sulphate. After elimination of the solvent the residue is purified through a silica gel column with methylene chloride/methanol (4:1) as eluant.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. concentrationconcentrated by evaporation
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. customAfter elimination of the solvent the residue is purified through a silica gel column with methylene chloride/methanol (4:1) as eluant

Sources & evidence

ORD record
ord-23c70e0af5624b8eb4d541feb1cd21ed
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Reaction notes

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