Diisopropylethylamine → Ethyl 3-[n-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methylamino]propionate

HRID 17427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17427
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:31][NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>ClCCl>[C:19]([C:7]1[C:5]2[N:6]=[C:2]([CH2:31][NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[O:3][C:4]=2[C:10]([F:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH3:18])#[N:20]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 22629233Ethyl 3-(methylamino)propanoate hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 68585798Ethyl 3-[n-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methylamino]propionateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.49 g, 1.71 mmol), diisopropylethylamine (0.70 ml, 4.12 mmol) and ethyl 3-(methylamino)propionate hydrochloride (I-159) (0.32 g, 1.91 mmol) were dissolved in dichloromethane (15 ml). After heated under reflux for 3 hours, this was diluted with dichloromethane. After washed with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70; 1), then again purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1) to obtain the entitled compound (0.53 g, 81%) as a brown oil.

Aufarbeitung

  1. temperatureAfter heated
  2. temperatureunder reflux for 3 hours
  3. washAfter washed with water
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70; 1)
  7. customagain purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e71dad24ae02472486fdc06f7f991ab3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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