1-(2-Hydroxyethyl)piperazine → 4-Chloro-7-{5-[4-(2-hydroxyethyl)piperazin-1-ylcarbonyl]-1-methylindol-2-yl}isoindolinone

HRID 21104

Reaktionsgleichung

Reaktionsgleichung von HRID 21104
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([C:20](O)=[O:21])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:24].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[OH:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([C:20]([N:53]2[CH2:54][CH2:55][N:50]([CH2:49][CH2:48][OH:47])[CH2:51][CH2:52]2)=[O:21])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:24]

Komponenten

8

Edukt 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 684921784-Chloro-7-(5-carboxy-1-methylindol-2-yl)isoindolinone

Produkt 1

HCID 684874834-Chloro-7-{5-[4-(2-hydroxyethyl)piperazin-1-ylcarbonyl]-1-methylindol-2-yl}isoindolinoneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Example 20, Compound 157 (20.0 mg, 0.0587 mmol) was dissolved in DMF (1 mL), and the solution was treated with EDCI (23 mg, 0.12 mmol), HOBT monohydrate (7.9 mg, 0.059 mmol) and 1-(2-hydroxyethyl)piperazine (31 mg, 0.24 mmol). The mixture was added with water and ethyl acetate and extracted with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium carbonate to adjust the pH to 9 and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in chloroform, and the solution was added with hexane and stirred for 30 minutes. The solid was collected by filtration and washed with hexane, followed by drying under reduced pressure to obtain Compound 159 (18.5 mg, yield 70%).

Aufarbeitung

  1. extractionextracted with 1 mol/L hydrochloric acid
  2. additionThe aqueous layer was added with sodium carbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in chloroform
  8. additionthe solution was added with hexane
  9. filtrationThe solid was collected by filtration
  10. washwashed with hexane
  11. customby drying under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5f6354f3c19e49c0b1987e6e923596f9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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