Trifluoroacetic acid → 2-(6-Dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetamide

HRID 402889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402889
O.[OH-].[Li+].C([O:6][C:7](=O)[CH2:8][C:9]1[N:13]2[CH:14]=[C:15]([CH2:18][N:19]([CH3:21])[CH3:20])[CH:16]=[CH:17][C:12]2=[N:11][CH:10]=1)C.FC(F)(F)C(O)=O.C(N1C=CN=C1)([N:32]1C=CN=C1)=O>O1CCOCC1.O>[CH3:20][N:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]2[N:13]([C:9]([CH2:8][C:7]([NH2:32])=[O:6])=[CH:10][N:11]=2)[CH:14]=1)[CH3:21]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 168937Lithium hydroxide, monohydrateHCID 59192025(6-Dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 591920412-(6-Dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (55 mg, 1.31 mmol, 1.5 equiv) is added to a solution of (6-dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid ethyl ester (240 mg, 0.87 mmol) in dioxane (10 ml) and water (10 ml). After 1 hour at room temperature, the reaction mixture is concentrated in vacuo. The residue is taken up in N,N-dimethylformamide (10 ml) and treated with trifluoroacetic acid (0.34 ml, 4.5 mmol, 4.5 equiv). Carbonyldiimidazole (167 mg, 0.98 mmol, 1.0 equiv) is added, and the mixture is stirred at room temperature for 1 hour. After removal of the solvent, concentrated aqueous ammonia (10 ml) is added to the activated acid. The mixture is stirred at room temperature for 30 minutes. Volatiles are removed in vacuo, and purification of the residue via flash chromatography (CH2Cl2/MeOH 7:3) affords the title compound (186 mg, 76%). 1H NMR (400 MHz, d4-MeOH): δ=8.31 (s, 1H), 7.55 (d, J=9.0 Hz, 1H), 7.49 (s, 1H), 7.35 (dd, J=9.0/1.5 Hz, 1H), 3.95 (s, 2H), 3.71 (s, 2H), 2.42 (s, 6H). MS (ES+): 233 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customAfter removal of the solvent, concentrated aqueous ammonia (10 ml)
  3. additionis added to the activated acid
  4. stirringThe mixture is stirred at room temperature for 30 minutes
  5. customVolatiles are removed in vacuo, and purification of the residue via flash chromatography (CH2Cl2/MeOH 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-08bb8308c0f7495cb229da771d7cc79c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742132B2

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