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Dimethylformamide → HCID 59824929, Verbindung

HRID 886569
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 886569
[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[N:23]=[C:22]([CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.CN(C)C=[O:43].[OH-].[K+]>CO>[OH:43][CH:24]([C:22]1[CH:21]=[N:20][CH:19]=[C:18]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][NH:11][C:12]3=[N:13][CH:14]=2)[N:23]=1)[C:25]([N:27]([CH3:29])[CH3:28])=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 59297027HCID 59297027, Verbindung

Produkt 1

HCID 59824929HCID 59824929, VerbindungAusbeute 22,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Crude 2-{6-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-N,N-dimethyl-acetamide (0.271 mmol) was dissolved in methanol (1 mL) and dimethylformamide (1 mL) and 50% w/v aqueous potassium hydroxide (0.5 mL) was added. After 30 minutes, the reaction was quenched by addition of acetic acid (0.5 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 2-hydroxy-2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-N,N-dimethyl-acetamide (25 mg, 22.8%, 3 steps). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.32 (s, 3H), 2.78 (s, 3H), 3.79 (s, 3H), 5.37 (m, 1H), 5.61 (m, 1H), 7.03 (dt, J=7.0 Hz, 1H), 7.12 (br d, J=8.5 Hz, 1H), 7.29 (br dt, J=7.5 Hz, 1H), 7.57 (dd, J=7.5 Hz, 1H), 7.79 (br t, 1H), 8.47 (d, 1H), 8.61 (d, 1H), 8.65 (d, 1H), 8.75 (d, 1H). MS: m/z 404 (M+H+).

Aufarbeitung

  1. additionwas added
  2. customthe reaction was quenched by addition of acetic acid (0.5 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried to a residue which
  8. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-99cc569724054afa8779e9b831da99c2
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242280B2

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