Triethylamine → 8-(trans-2,3-Dihydro-2-hydroxy-7-methoxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053044
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]([OH:16])[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=1)=[O:4].[O:18]1[CH:20]2[CH2:21][C:22]3[C:27]([CH:19]12)=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][CH:23]=3.C(N(CC)CC)C>C(O)C.O>[OH:18][C@@H:20]1[CH2:21][C:22]2[C:27](=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][CH:23]=2)[C@H:19]1[O:16][C:7]1[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=[C:5]([C:3]([N:2]([CH3:1])[CH3:17])=[O:4])[CH:6]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 237308448-Hydroxy-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamideHCID 866048921,2-Epoxy-7-methoxy-indane

Produkt 1

HCID 691058528-(trans-2,3-Dihydro-2-hydroxy-7-methoxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridineAusbeute 19,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 0.8 g (3.4 mmol) 6-(N,N-dimethylamino-carbonyl)-8-hydroxy-2,3-dimethyl-imidazo[1,2-a]pyridine in 16 ml ethanol and 4 ml water are added 1.0 g (6.2 mmol) 1,2-epoxy-7-methoxy-indane and 0.48 ml triethylamine. After 4 h at 30° C., the mixture is cooled down and partitioned between di-chloromethane and saturated aqueous ammonium chloride. The organic layer is separated, dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using ethyl acetate:light petroleum ether:triethylamine (8:1:1) yields 0.26 g (19%) of the title compound as a colourless solid (m.p. 129° C.).

Aufarbeitung

  1. temperaturethe mixture is cooled down
  2. custompartitioned between di-chloromethane and saturated aqueous ammonium chloride
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customPurification of the residue by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0ab497e3a38840eabe6700fbfb63f38b
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326718B2

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