Dichloromethane → (E)-3-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylic acid hydrochloride

HRID 2172087

Reaktionsgleichung

Reaktionsgleichung von HRID 2172087
FC(F)(F)C(O)=O.[O:8]=[C:9]1[NH:26][C:12]2=[N:13][CH:14]=[C:15](/[CH:17]=[CH:18]/[C:19]([O:21]C(C)(C)C)=[O:20])[CH:16]=[C:11]2[NH:10]1.[Cl:27]CCl>>[ClH:27].[O:8]=[C:9]1[NH:26][C:12]2=[N:13][CH:14]=[C:15](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH:16]=[C:11]2[NH:10]1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68338066(E)-tert-butyl 3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylate

Produkt 1

HCID 70926863(E)-3-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylic acid hydrochloride

Versuchsvorschrift

Trifluoroacetic acid (2 mL) was added to a suspension of (E)-tert-butyl 3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylate (400 mg, 1.54 mmol) in dichloromethane (2 mL) at room temperature. The reaction mixture was stirred for 1 hour then concentrated to dryness. The resulting residue was suspended in a solution of hydrochloric acid in dioxane 4N (2 mL). After 10 minutes stirring at room temperature, the precipitate was filtered and washed with diethyl ether to afford the title product as a pale yellow solid (381 mg, quantitative).

Aufarbeitung

  1. concentrationthen concentrated to dryness
  2. stirringAfter 10 minutes stirring at room temperature
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a430f365f03f416c90237ade1a6023d1
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051321B2

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