Potassium Carbonate → HCID 71288191, Verbindung

HRID 245930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245930
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C@H:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[N:14]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:13]=1)=[O:11])[CH3:8])=O.CCN(S(F)(F)F)CC.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:1]1[CH2:2][CH2:3][N:4]=[C:5]1[C@H:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[N:14]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[CH:13]=1)=[O:11])[CH3:8]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 712881872-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-amide

Produkt 1

HCID 71288191HCID 71288191, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-76 °C

Versuchsvorschrift

In a round-bottomed flask, 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-amide (126 mg, 0.23 mmol) was dissolved in dichloromethane (2.2 ml). The solution was cooled to −76° C. and DAST (45 μl, 0.34 mmol) was added. The pale yellow reaction mixture was stirred at −76° C. for 6 h then anhydrous potassium carbonate (64 mg, 0.46 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature, quenched with saturated aqueous NaHCO3 and extracted with dichloromethane (3×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-90% EtOAc) to afford 86 mg (71%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4,5-dihydro-oxazol-2-yl)-ethyl]-amide as a light yellow solid.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customquenched with saturated aqueous NaHCO3
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-90% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e0b71cac531f4477a2e5559cd5c85da0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

Notizen zur Reaktion

Wird geladen…