Potassium Carbonate → 4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid

HRID 1510288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510288
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[N:17]=[C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:19][C:20]=3[C:21]([F:24])([F:23])[F:22])=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.F[C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][N:33]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:25]1([C:18]2[O:19][C:20]([C:21]([F:22])([F:23])[F:24])=[C:16]([C:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([CH:4]4[CH2:5][CH2:6][N:1]([C:32]5[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][N:33]=5)[CH2:2][CH2:3]4)=[CH:12][CH:11]=3)=[O:15])[N:17]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2428196-Fluoronicotinic AcidHCID 529371572-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide

Produkt 1

HCID 468338084-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acidAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide (208 mg, 0.5 mmol) and 6-fluoronicotinic acid (72 mg, 0.5 mmol) in DMSO (2 L) containing potassium carbonate (135 mg, 1 mmol) was heated in a microwave at 135° C. for 35 minutes. The mixture was extracted with ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with water and brine. Solvents were evaporated and the residue was purified through ISCO column chromatography (silica gel, ethyl acetate in hexanes, 10% to 100% linear gradient). The collected fractions were concentrated and the white crystalline material was filtered to give 4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (40.5 mg). LC-MS for C28H23F3N4O4 (m/e) calcd 536, obsd 537 (M+H). 1H-NMR is consistent with the desired structure.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate and 0.1N hydrochloric acid
  2. washThe organic layer was washed with water and brine
  3. customSolvents were evaporated
  4. customthe residue was purified through ISCO column chromatography (silica gel, ethyl acetate in hexanes, 10% to 100% linear gradient)
  5. concentrationThe collected fractions were concentrated
  6. filtrationthe white crystalline material was filtered

Quellen und Nachweise

ORD-Eintrag
ord-b0af23d89d404c2b87ee4f40c3a1a8f9
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211914B2

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