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Sodium → N-(2-Hydroxymethylthiazolo[5,4-b]pyrid-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 2069526
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2069526
[Na].CC(C)(C)C([O:6][CH2:7][C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([NH:17][C:18]([C:20]1[N:21]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[C:22]3[C:27]([CH:28]=1)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=3)=[O:19])=[CH:12][N:11]=2)=O>CO>[OH:6][CH2:7][C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([NH:17][C:18]([C:20]1[N:21]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[C:22]3[C:27]([CH:28]=1)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=3)=[O:19])=[CH:12][N:11]=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 5360545SodiumHCID 66888934HCID 66888934, Verbindung2×

Produkt 1

HCID 44181666N-(2-Hydroxymethylthiazolo[5,4-b]pyrid-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

50 mg (2.03 mmol) of sodium are added to 8 mL of methanol with stirring at 20° C. After 15 minutes, a solution of 0.15 g (0.28 mmol) of [6-[[[5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indol-2-yl]carbonyl]amino]thiazolo[5,4-b]pyrid-2-yl]methyl 2,2-dimethylpropanoate (Compound 13), prepared in step 4.3, in 16 mL of methanol is added. Stirring is continued for 15 minutes at 20° C., and the reaction mixture is then concentrated under reduced pressure and taken up in 200 mL of molar ammonium chloride solution. The aqueous phase is extracted three times with 50 mL of ethyl acetate. The organic phases are combined, washed with 50 mL of saturated sodium chloride solution and then dried over sodium sulfate and concentrated under reduced pressure. The product thus obtained is purified on a column of silica, eluting with a mixture of dichloromethane and methanol. 70 mg of the expected product are thus isolated.

Aufarbeitung

  1. additionis added
  2. stirringStirring
  3. waitis continued for 15 minutes at 20° C.
  4. concentrationthe reaction mixture is then concentrated under reduced pressure
  5. extractionThe aqueous phase is extracted three times with 50 mL of ethyl acetate
  6. washwashed with 50 mL of saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe product thus obtained
  10. customis purified on a column of silica
  11. washeluting with a mixture of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-c397f6602dac48dcb40a7624ce67402b
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299114B2

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