Diisopropylethylamine → SB-649,915

HRID 1295582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295582
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=2)[CH2:4][CH2:3]1.Br[CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28]([CH3:34])=[N:29]2.C(N(C(C)C)CC)(C)C>C(O)(C)C>[CH3:34][C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[CH:31][CH:32]=[CH:33][C:24]=2[O:23][CH2:22][CH2:21][N:2]2[CH2:7][CH2:6][CH:5]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]4[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=4[CH:19]=3)[CH2:4][CH2:3]2)[N:29]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 117371925-(2-Bromoethoxy)-2-methylquinolineHCID 223266516-(4-piperidinylmethyl)-4H-benzo[1,4]oxazin-3-one hydrochloride

Produkt 1

HCID 10296414SB-649,915Ausbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 6-(4-piperidinylmethyl)-4H-benzo[1,4]oxazin-3-one hydrochloride (0.10 g, 0.35 mmol), 5-(2-bromoethoxy)-2-methylquinoline (0.11 g, 0.42 mmol), diisopropylethylamine (1 mL) and isopropanol (10 mL) was heated at reflux under argon for 48 h, cooled, then evaporated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (50 mL) and dichloromethane (3×30 mL) and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The resulting oil was purified by chromatography on silica eluting with 50% ethyl acetate-hexane followed by 0–25% methanol-ethyl acetate gradient elution, to give the title compound (0.04 g, 26%) as an oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under argon for 48 h
  3. temperaturecooled
  4. customevaporated in vacuo
  5. customThe residue was partitioned between saturated aqueous NaHCO3 (50 mL) and dichloromethane (3×30 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting oil was purified by chromatography on silica eluting with 50% ethyl acetate-hexane
  9. washfollowed by 0–25% methanol-ethyl acetate gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-3ff4cc4fcbbb472faba08f618c65d786
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244726B2

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