Ethanol → 2-{3-(4-Hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetic acid

HRID 507748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507748
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([O:16]CC)=[O:15])[N:11]=[C:10]3[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([NH:27][C:28]([NH:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[O:29])[C:24]=4[C:25](=[O:26])[C:9]=23)=[CH:4][CH:3]=1.O1CCOCC1.C(O)C.[OH-].[Na+]>CCOC(C)=O.CS(C)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([OH:16])=[O:15])[N:11]=[C:10]3[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([NH:27][C:28]([NH:30][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[O:29])[C:24]=4[C:25](=[O:26])[C:9]=23)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 136352541Ethyl 2-{3-(4-hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetate

Produkt 1

HCID 1357740212-{3-(4-Hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 37 (1.2 g, 2.4 mmol) was dissolved in 60 ml 3:2:1; dioxane:ethanol:DMSO and 12 ml 0.5 N NaOH added and the reaction became red. The reaction mixture was stirred at room temperature for one hour, diluted with EtOAc and washed with 1N HCl. The aqueous layer was back extracted once with ethyl acetate and the combined organic layers dried over MgSO4 and concentrated to an orange solid. The solid was triturated with 10 ml MeOH/100 ml Et2O, filtered off and dried to a solid (1.1 g, 2.4 mmol, 100%, compound 38: designated G7).

Aufarbeitung

  1. washwashed with 1N HCl
  2. extractionThe aqueous layer was back extracted once with ethyl acetate
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated to an orange solid
  5. customThe solid was triturated with 10 ml MeOH/100 ml Et2O
  6. filtrationfiltered off
  7. dry with materialdried to a solid (1.1 g, 2.4 mmol, 100%, compound 38: designated G7)

Quellen und Nachweise

ORD-Eintrag
ord-9236518e15394e3ebc70794bea073eb4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786112B2

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