Sodium Carbonate → HCID 57965001, Verbindung

HRID 1931691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931691
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[N:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[C:31]3=[N:32][CH:33]=[N:34][C:35](Cl)=[C:30]3[CH:29]=[N:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH2:23][CH:24]([N:27]2[C:31]3=[N:32][CH:33]=[N:34][C:35]([O:13][C:10]4[CH:11]=[CH:12][C:7]([C:4]5[N:3]=[C:2]([CH3:1])[O:6][N:5]=5)=[CH:8][CH:9]=4)=[C:30]3[CH:29]=[N:28]2)[CH2:25][CH2:26]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 49623974-(5-Methyl-1,2,4-oxadiazol-3-yl)phenolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Produkt 1

HCID 57965001HCID 57965001, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenol (Enamine Ltd., Kiev, Ukraine; 32 mg, 0.178 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 60 mg, 0.178 mmol), and potassium carbonate (54 mg, 0.391 mmol) in dimethylformamide (1 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture, and the mixture was then filtered through a pad of silica gel to remove the precipitate. The silica gel pad was washed with methanol and the solvents were evaporated from the filtrate. The residue was purified by HPLC to afford 4-{4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyrazolo[3,4-d]pyrimidin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (17 mg, 20%) as an off white solid. Mass spectrum M+H-Boc=378.

Aufarbeitung

  1. filtrationthe mixture was then filtered through a pad of silica gel
  2. customto remove the precipitate
  3. washThe silica gel pad was washed with methanol
  4. customthe solvents were evaporated from the filtrate
  5. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-87206d0af69140efbe8854599e2be0f9
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188098B2

Notizen zur Reaktion

Wird geladen…