Citric Acid → HCID 57731537, Verbindung

HRID 2234696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234696
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:29][C:30]4[CH:31]=[N:32][CH:33]=[N:34][CH:35]=4)=[C:22]([CH:28]=3)[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:29][C:30]4[CH:31]=[N:32][CH:33]=[N:34][CH:35]=4)=[C:22]([CH:28]=3)[C:23]([N:25]([CH3:26])[CH3:27])=[O:24])[CH:16]=2)[NH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 57731440HCID 57731440, Verbindung

Produkt 1

HCID 57731537HCID 57731537, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

67 mg (0.11 mmol) of 5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide was dissolved in 3 mL of hot ethanol. 200 μL of 50% w/v aqueous potassium hydroxide was added and the mixture left at ambient temperature for 4.5 h. 10% w/v aqueous citric acid was added and the mixture partitioned between dichloromethane and water. The aqueous layer was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by mass-triggered reverse-phase HPLC to afford 21.9 mg (47 μmol, 43%) of 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide as a beige solid. 1H-NMR (500 MHz, d6-DMSO): δ 11.91 (s, br., 1H), 8.64 (s, 1H), 8.55 (d, 1H), 8.51 (s, 2H), 8.17 (d, 1H), 8.12 (s, 1H), 7.74 (d, 1H), 7.73 (dd, 1H), 7.63-7.61 (m, 2H), 7.39 (d, 1H), 7.30 (dd(d), 1H), 7.14 (d, 1H), 7.06 (t, 1H), 3.83 (s, 3H), 2.90 (s, 3H), 2.88 (s, 3H); MS: m/z 465.0 (M+H+).

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. customthe mixture partitioned between dichloromethane and water
  4. extractionThe aqueous layer was extracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by mass-triggered reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-43fff49cf0c34dfeabebb669591c7855
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709645B2

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