1-Butanol → butyl 2-(1-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetate

HRID 2381752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381752
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH2:28][CH2:27]2.C[Si](Cl)(C)C.[CH2:40](O)[CH2:41]CC>>[O:34]=[C:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][CH:33]=[C:24]([NH:23][C:2]3[N:3]=[C:4]([N:11]4[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH2:21][CH2:22][CH2:40][CH3:41])=[O:19])[CH2:13][CH2:12]4)[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)[CH:25]=2)[NH:30]1

Komponenten

5

Edukt 4

HCID 2631-ButanolHCID 6397Chlorotrimethylsilane2×HCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 57990296ethyl 2-(1-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetate

Produkt 1

HCID 57990317butyl 2-(1-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetate

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of ethyl 2-(1-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetate (135 mg, 0.419 mmol), 6-amino-3,4-dihydroquinolin-2(1H)-one (97 mg, 0.600 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in nBuOH (4 mL) was stirred at 135° C. for 20 h. More trimethylsilyl chloride (0.200 mL, 1.58 mmol) was added. It was stirred at 135° C. for another 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (54 mg). MS 477.3 (M+H); UV 200.0, 279.8 nm.

Aufarbeitung

  1. stirringIt was stirred at 135° C. for another 20 h
  2. concentrationIt was concentrated in vacuo
  3. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f6e43175f3014d15bfc9597d02cfeb5b
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258144B2

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