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Ethyl Bromide → 5-[1-(1-Ethyl-4-piperidyl)pyrazol-4-yl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

HRID 908462
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 908462
Br[CH2:2][CH3:3].[O:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:13]1[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:2]([N:27]1[CH2:26][CH2:25][CH:24]([N:22]2[CH:23]=[C:19]([C:17]3[CH:18]=[C:13]([C:5]4[O:4][C:12]5[C:7]([N:6]=4)=[N:8][CH:9]=[CH:10][CH:11]=5)[C:14]([NH2:30])=[N:15][CH:16]=3)[CH:20]=[N:21]2)[CH2:29][CH2:28]1)[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 576870643-Oxazolo[4,5-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

Produkt 1

HCID 576871065-[1-(1-Ethyl-4-piperidyl)pyrazol-4-yl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Bromoethane (0.019 ml) at 0° C. was added to a stirred mixture of 3-oxazolo[4,5-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (90 mg) and potassium carbonate (68.8 mg) and DMF (1.5 mL) over a period of 5 minutes under argon. The resulting suspension was stirred at 25° C. for 20 hours. The solvent was evaporated. A solution of ammonia in methanol 7N (1 ml) was added and the mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 5-[1-(1-ethyl-4-piperidyl)pyrazol-4-yl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (60.0 mg) as a solid. NMR Spectrum: (DMSOd6) 1.03 (t, 3H), 1.91-2.10 (m, 6H), 2.38 (q, 2H), 2.94-3.01 (m, 2H), 4.09-4.18 (m, 1H), 7.48 (dd, 1H), 7.67 (bs, 2H), 7.92 (s, 1H), 8.23 (dd, 1H), 8.34 (s, 1H), 8.46 (d, 1H), 8.55 (dd, 1H), 8.58 (d, 1H); Mass spectrum: M+H+ 390.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionA solution of ammonia in methanol 7N (1 ml) was added
  3. customThe crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane
  4. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-12b0f836cf9d4ebdb71956056007ec41
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08017611B2

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