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Diisopropylethylamine → 1-[(6-Methyl-3-pyridinyl)carbonyl]-4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine

HRID 43409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 43409
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[F:16][C:17]([F:30])([F:29])[O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:29])[F:30])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 167870611-[(6-Methylpyridin-3-YL)carbonyl]piperazine

Produkt 1

HCID 302859691-[(6-Methyl-3-pyridinyl)carbonyl]-4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazineAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 1-[(6-methyl-3-pyridinyl)carbonyl]piperazine (may be prepared as described in Description 14) (100 mg, 0.487 mmol) in DMF (10 ml) was added 4-[(trifluoromethyl)oxy]benzenesulfonyl chloride (152 mg, 0.585 mmol). Finally DIPEA (0.255 ml, 1.462 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. Solvent was removed by evaporation, the residue was dissolved in ethyl acetate and the solution extracted with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and evaporated to dryness and the residue was purified by MDAP to yield the title compound (42 mg) as a white powder.

Aufarbeitung

  1. customSolvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionthe solution extracted with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthe residue was purified by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-51c133a4797542e6a0a82ff1f95be02d
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08536183B2

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