1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 69449611, Verbindung

HRID 1296703

Reaktionsgleichung

Reaktionsgleichung von HRID 1296703
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:15]([C:16](=[O:18])[CH3:17])=[C:11]3[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[CH:31](OC(C)(C)C)[N:32]([CH3:34])[CH3:33])(C)(C)C>>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)[C:15]([C:16](=[O:18])[CH:17]=[CH:31][N:32]([CH3:34])[CH3:33])=[C:11]3[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

3

Edukt 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 694487401-[7-(Cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]ethanone

Produkt 1

HCID 69449611HCID 69449611, VerbindungAusbeute 69 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 1-[7-(cyclopentylamino)-2-(4fluorophenyl)pyrazolo[1,5- c]pyrimidin-3-yl]ethanone (200 mg, 0.59 mmol) was added 1,1 -di-tert-butoxy-N,N-dimethylmethanamine (4 mL) and the mixture heated to 80° C. for 30 minutes. The reaction was let cool to room temperature and was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with water and brine. The ethyl acetate solution was dried over magnesium sulfate, filtered and concentrated. The resulting residue was purified by silica chromatography eluting with ethyl acetate to yield 160 mg (69%) of 1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-3-(dimethylamino)prop-2-en-1-one. 1H NMR (CDCl3): δ 7.77 (m, 4H), 7.44 (d, 1H), 7.19 (t, 2H), 6.41 (d, 1H), 5.09 (d, 1H), 4.57 (m,1H), 3.07 (m, 3H), 2.60 (m, 3H), 2.25 (m, 2H), 1.85 (m, 6H). MS m/z 394 (M+1).

Aufarbeitung

  1. temperatureThe reaction was let cool to room temperature
  2. customwas partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with water and brine
  5. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica chromatography
  9. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-73c873095ea74f5883eafeaee0dadd4c
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07247626B2

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