Diisopropylethylamine → N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-5-(4-fluorophenyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydropyridine-3-carboxamide

HRID 1428099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428099
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:31])[C:19]([C:28](O)=[O:29])=[CH:20][N:21]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:22]=2)=[CH:13][CH:12]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.[NH2:59][C:60]1[CH:65]=[CH:64][C:63]([C:66]2[C:67]([NH2:73])=[N:68][CH:69]=[C:70]([Br:72])[CH:71]=2)=[CH:62][CH:61]=1>CN(C=O)C.O>[NH2:73][C:67]1[C:66]([C:63]2[CH:62]=[CH:61][C:60]([NH:59][C:28]([C:19]3[C:18](=[O:31])[C:17]([C:14]4[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=4)=[CH:22][N:21]([CH2:23][C:24]([F:26])([F:25])[F:27])[CH:20]=3)=[O:29])=[CH:65][CH:64]=2)=[CH:71][C:70]([Br:72])=[CH:69][N:68]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 682889763-(4-Aminophenyl)-5-bromopyridin-2-amineHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 867000505-(4-Fluorophenyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydropyridine-3-carboxylic acid

Produkt 1

HCID 86700049N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-5-(4-fluorophenyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydropyridine-3-carboxamideAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (414 μl) was added to a solution of the compound obtained in Step 2 of Example 9 (500 mg) and COMU (883 mg) in DMF (8.0 ml) at room temperature, and the mixture was stirred for 25 minutes. The compound obtained in Step 1 of Example 1 (440 mg) was added at room temperature. The mixture was stirred for 19 hours, followed by the addition of water. The precipitated solid was collected by filtration, suspended in chloroform/diisopropyl ether and then collected by filtration to give 800 mg of the title compound.

Aufarbeitung

  1. stirringThe mixture was stirred for 19 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e7de9642c0cb4c41a951320a01d92bba
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933103B2

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