Sodium Chloride → 5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 1695395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695395
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([C:21]([OH:23])=O)[N:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[NH2:45][C:46]([CH3:50])([CH3:49])[CH2:47][OH:48].[Cl-].[Na+]>C1COCC1>[OH:48][CH2:47][C:46]([NH:45][C:21]([C:17]1[N:18]([CH3:20])[N:19]=[C:15]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2[CH3:24])[CH:16]=1)=[O:23])([CH3:50])[CH3:49]

Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 118072-Amino-2-methyl-1-propanolHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66643617HCID 66643617, Verbindung

Produkt 1

HCID 595684165-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.3 mmol) in THF (2.7 mL) was added 1-hydroxybenzotriazole hydrate (47.2 mg, 0.3 mmol), N-ethyldiisopropylamine (131.9 μL, 0.76 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidazole hydrochloride (59.1 mg, 0.3 mmol) and 2-amino-2-methyl-1-propanol (27.8 mg, 0.3 mmol) and the resulting mixture stirred overnight at room temperature. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5) afforded the title compound (115 mg, 94%) as a white solid. MS: m/e=403.2 [M+H]+.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. concentrationConcentration and purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-6edd58e4f6564188a721a0b5ef797ef5
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163728B2

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