Dimethyl Sulfoxide → N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide

HRID 230804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230804
C(N(CC)CC)C.CS(C)=O.[OH:12][CH2:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:40])[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:28][CH:27]=3)=[CH:20][N:19]2[C:41]=1[CH3:42]>O>[CH3:42][C:41]1[N:19]2[CH:20]=[C:21]([NH:24][C:25](=[O:40])[C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:30][CH:31]=3)[CH:22]=[CH:23][C:18]2=[N:17][C:16]=1[CH2:15][CH2:14][CH:13]=[O:12]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57763130N-[2-(3-hydroxypropyl)-3-methylimidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide

Produkt 1

HCID 86615940N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamideAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Triethylamine (87.9 μL) and sulfur trioxide-pyridine complex (46.3 mg) were added to a DMSO solution (3 mL) of the compound (20.0 mg) obtained in Example 14, at room temperature. After stirred for 11 hours, the reaction liquid was poured into saturated saline water, and extracted with chloroform. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel chromatography (methanol/chloroform=1/25 to 1/8) to obtain N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide (10.8 mg).

Aufarbeitung

  1. customthe reaction liquid
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel chromatography (methanol/chloroform=1/25 to 1/8)

Quellen und Nachweise

ORD-Eintrag
ord-735b33487d054610a492fbf6682aca76
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566781B2

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