Diisopropylethylamine → N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-1-ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxamide

HRID 1428092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428092
CCN(C(C)C)C(C)C.[CH2:10]([N:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:24])[C:14]([C:25]([OH:27])=O)=[CH:13]1)[CH3:11].CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.[NH2:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]2[C:63]([NH2:78])=[N:64][CH:65]=[C:66]([C:68]3[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[C:70]([O:76][CH3:77])[CH:69]=3)[CH:67]=2)=[CH:58][CH:57]=1>CN(C=O)C.O>[NH2:78][C:63]1[C:62]([C:59]2[CH:58]=[CH:57][C:56]([NH:55][C:25]([C:14]3[C:15](=[O:24])[C:16]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:17][N:12]([CH2:10][CH3:11])[CH:13]=3)=[O:27])=[CH:61][CH:60]=2)=[CH:67][C:66]([C:68]2[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[C:70]([O:76][CH3:77])[CH:69]=2)=[CH:65][N:64]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 126242271-Ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxylic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 86700031HCID 86700031, Verbindung

Produkt 1

HCID 86700042N-{4-[2-Amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-1-ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxamideAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (601 μl) was added to a solution of 1-ethyl-4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxylic acid (420 mg) and COMU (961 mg) in DMF (5.0 ml) at room temperature, and the mixture was stirred for 20 minutes. The compound obtained in Step 2 of Example 1 (610 mg) was added at room temperature. The mixture was stirred for 15 hours, followed by the addition of water. The organic layer was extracted with ethyl acetate, and then washed with water and brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->60:1 (v/v)] to give 700 mg of the title compound as a solid.

Aufarbeitung

  1. stirringThe mixture was stirred for 15 hours
  2. extractionThe organic layer was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->60:1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-98f9aa1bc1d341618a4de461f97c2d41
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933103B2

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