Triethylamine → (3-(4-((Dimethylamino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035230
Cl.[CH3:2][NH:3][CH3:4].Cl[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH:14]2[CH2:17][N:16]([C:18]([C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:23][N:24]=3)=[O:19])[CH2:15]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:2][N:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([S:13][CH:14]2[CH2:17][N:16]([C:18]([C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:23][N:24]=3)=[O:19])[CH2:15]2)=[CH:11][CH:12]=1)[CH3:4]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 10473Dimethylamine, hydrochloride2×HCID 58043149(3-(4-(Chloromethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Produkt 1

HCID 56598532(3-(4-((Dimethylamino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dimethylamine hydrochloride (0.10 g, 1.24 mmol) and 60B (0.16 g, 0.41 mmol) were mixed in DCM (5 ml). Triethylamine (0.290 ml, 2.07 mmol) was added and the mixture was stirred at RT for 2.5 h. More of triethylamine (0.290 ml, 2.07 mmol) and dimethylamine hydrochloride (0.10 g, 1.24 mmol) were added. The mixture was stirred overnight at RT and then diluted with DCM (10 ml). The mixture was washed with water, filtered through a phase separator and then evaporated. The residue was purified by column chromatography eluting with NH3 in MeOH (2M)/DCM (1:99, 2:98). There was obtained 0.14 g (84%) of 60 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.20 (s, 6H), 3.38 (s, 2H), 4.16 (m, 2H), 4.61 (m, 2H), 5.07 (m, 1H), 7.50 (t, 2H), 7.56 (t, 1H), 8.12 (d, 2H), MS (APCI+) m/z 395 [M+H]+, LC purity: 97%.

Aufarbeitung

  1. stirringThe mixture was stirred overnight at RT
  2. washThe mixture was washed with water
  3. filtrationfiltered through a phase separator
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with NH3 in MeOH (2M)/DCM (1:99, 2:98)

Quellen und Nachweise

ORD-Eintrag
ord-b6d4978c5a0f4dd384bca65d937eba88
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546375B2

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