Isopropyl chloroformate → 5-[4-(Isopropyloxycarbonylamino)butylthio]imidazo[1,2-a]pyridine

HRID 5486

Reaktionsgleichung

Reaktionsgleichung von HRID 5486
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]>C(Cl)Cl>[CH:27]([O:26][C:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)=[O:25])([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 233628945-[4-(Amino)butylthio]imidazo[1,2-a]pyridine

Produkt 1

HCID 233630025-[4-(Isopropyloxycarbonylamino)butylthio]imidazo[1,2-a]pyridineAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 5-(4-amino)butylthioimidazo[1,2-a]pyridine (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in methylene chloride (20 ml) was added isopropyl chloroformate (0.25 g, 2.04 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was washed in turn with aqueous saturated sodium bicarbonate and saturated saline, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 215 mg of the desired product (41.8%, light tan oily product).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 1 hour
  4. washThe reaction mixture was washed in turn with aqueous saturated sodium bicarbonate and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1b45aea4222d4467b64a679104b92b1b
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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