Dimethylformamide → tert-butyl [(1S)-2-{[1-(5-methoxy-1,3-benzothiazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

HRID 2368073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368073
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:5]=2[N:6]=1.[CH3:13][C@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C.CN(C=O)C>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([N:20]3[CH2:19][CH2:18][CH:17]([O:16][CH2:15][C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:13])[CH2:22][CH2:21]3)=[N:6][C:5]=2[CH:7]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 70592002-Chloro-5-methoxybenzothiazoleHCID 57517479tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate

Produkt 1

HCID 86658696tert-butyl [(1S)-2-{[1-(5-methoxy-1,3-benzothiazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-chloro-5-methoxy-1,3-benzothiazole (143 mg), tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate (186 mg), N,N-diisopropylethylamine (93 mg) and DMF (3 mL) was stirred at 150° C. for 1.5 hr under microwave irradiation. Water was added to the reaction mixture, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (194 mg).

Aufarbeitung

  1. extractionthe obtained mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-834d1e909bc244d8a1daed8837beede2
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703758B2

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