2-Fluorophenyl isocyanate → 3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carboxylic acid ethyl ester

HRID 75815

Reaktionsgleichung

Reaktionsgleichung von HRID 75815
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]=[C:26]=[O:27]>C1COCC1>[CH2:16]([O:15][C:13]([C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:26]([NH:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[F:18])=[O:27])=[CH:7][CH:6]=2)[CH:12]=1)=[O:14])[CH3:17]

Komponenten

4

Edukt 2

HCID 855882-Fluorophenyl isocyanateHCID 53407704Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate

Produkt 1

HCID 673543933-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carboxylic acid ethyl esterAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate (4 g) was dissolved in THF (80 ml). 2-Fluorophenyl isocyanate (2.83 g) was added and stirred at RT overnight. Reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography in 1:9 EtOAc: CHCl3 to get off white solid which was crystallized from CH2Cl2/Pet ether to yield 5 gm (78%) white solid. MS (ES+): m/z 370 (M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 9.32 (s, 1H), 8.62 (s, 1H), 8.12 (m, 1H), 7.89 (d, 2H), 7.81 (s, 1H), 7.59 (d, 2H), 7.24 (m, 1H), 7.12 (m, 1H), 7.05 (m, 1H), 4.38 (q, 2H), 1.31 (t, 3H).

Aufarbeitung

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by silica gel column chromatography in 1:9 EtOAc
  4. customCHCl3 to get off white solid which
  5. customwas crystallized from CH2Cl2/Pet ether

Quellen und Nachweise

ORD-Eintrag
ord-86dfde963e8a41e880dfadf2ce7de775
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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