Dimethylformamide → (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid N-methyl-N-(4-trifluoromethylphenyl)amide

HRID 856331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856331
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@:19]3([CH3:30])[O:23][C:22]4=[N:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][N:21]4[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])=[CH:5][CH:4]=1.[CH3:33]N(C=O)C.[H-].[Na+].CI>O>[CH3:33][N:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:31])[F:32])=[CH:8][CH:7]=1)[C:10]([N:12]1[CH2:13][CH2:14][N:15]([CH2:18][C@:19]2([CH3:30])[O:23][C:22]3=[N:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][N:21]3[CH2:20]2)[CH2:16][CH2:17]1)=[O:11]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86604818(S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid (4-trifluoromethylphenyl)amide

Produkt 1

HCID 69482847(S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid N-methyl-N-(4-trifluoromethylphenyl)amideAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid (4-trifluoromethylphenyl)amide prepared in Example 477 (200 mg, 0.44 mmol), DMF (4 ml), and sodium hydride (26 mg, 0.66 mmol) was stirred at room temperature for 1.5 hours. To the mixture, methyl iodide (0.5 ml, 0.76 mmol) was added followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with water three times and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid N-methyl-N-(4-trifluoromethylphenyl)amide (35 mg, yield 17%) as a white powder.

Aufarbeitung

  1. stirringby stirring at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water three times
  4. dry with materiala saturated saline solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-aa6c8408f2ac4dda8843a2c162afe26b
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262212B2

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