Diisopropylamine → HCID 76765796, Verbindung

HRID 69398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69398
[CH2:1]([NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:30])[CH2:2][CH2:3][CH3:4].C(NC(C)C)(C)C.C([Li])CCC>O1CCCC1>[CH2:1]([NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:14][OH:15])[CH:17]=[C:16]([C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[C:18]([F:19])([F:21])[F:20])=[CH:9][C:8]=1[CH3:30])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 7912DiisopropylamineHCID 67295194HCID 67295194, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 76765796HCID 76765796, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-butyl-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide (made as described in EP 1,731,512) (1670 mg, 4.13 mmol) and N,N-diisopropylamine (880 mg, 8.69 mmol) in dry tetrahydrofuran (10 ml) was added n-butyl lithium (“n-BuLi”) (1.55M in hexane) (5.6 ml, 8.69 mmol) at −90° C. The reaction mixture was allowed to warm to 0° C. over a period of 2 hours and quenched by addition of aqueous ammonium chloride (saturated). The mixture was extracted several times with diethyl ether. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 2:1) to give N-butyl-4-[3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-1-hydroxyimino-but-2-enyl]-2-methyl-benzamide (1180 mg, 70% yield) as a yellow resin. 1H-NMR (CDCl3, 300 MHz): 8.52 (bs, 1H), 7.45-7.36 (m, 6H), 6.75 (s, 1H), 5.81 (m, 1H), 3.46-3.43 (m, 2H), 2.47 (s, 3H), 1.54-1.39 (m, 4H), 0.97 (t, 3H) ppm.

Aufarbeitung

  1. customquenched by addition of aqueous ammonium chloride (saturated)
  2. extractionThe mixture was extracted several times with diethyl ether
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e244720a0e774435a15b3bc3d2ca2a8c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822502B2

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