Citric Acid → 6-Carbamoylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 570343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570343
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O:14]CC)=[O:13])=[CH:10][N:11]=2)[CH:8]=1)#[N:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:22]>C1COCC1.CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([OH:14])=[O:13])=[CH:10][N:11]=2)[CH:8]=1)(=[O:22])[NH2:2]

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67259960Ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate

Produkt 1

HCID 679761586-Carbamoylimidazo[1,2-a]pyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirring solution of ethyl 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate (24q) (500 mg, 2.32 mmol) in THF:MeOH (4:1, 5 mL) was added 2N LiOH (4 mL). The reaction was heated at 60° C. for 2 h then acidified with 10% citric acid. The solvent was partially concentrated and the resulting solid was collected by vacuum filtration and was washed with excess water. The product was purified from the crude solid to afford 6-carbamoylimidazo[1,2-a]pyridine-3-carboxylic acid (110). 1H NMR (400 MHz, d6-DMSO) δ 9.80 (s, 1H), 8.33-8.31 (m, 1H), 8.29 (s, 1H), 7.95 (dd, J=2.0, 9.6 Hz, 1H), 7.83 (dd, J=0.8, 9.2 Hz, 1H), 7.69 (s, 1H). MS m/z 205.05 (M+1)+.

Aufarbeitung

  1. concentrationThe solvent was partially concentrated
  2. filtrationthe resulting solid was collected by vacuum filtration
  3. washwas washed with excess water
  4. customThe product was purified from the crude solid

Quellen und Nachweise

ORD-Eintrag
ord-9b4405fc3d0d4a938a6589a9d30783f6
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023839B2

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