Methanesulfonyl chloride → HCID 57786156, Verbindung

HRID 1398962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398962
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH2:22][CH2:23]O)[C:6]=2[C:5]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.CS(Cl)(=O)=O>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:12]4[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=4[O:20][CH3:21])[CH2:23][CH2:22][N:7]3[C:6]=2[C:5]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58012359HCID 58012359, Verbindung

Produkt 1

HCID 57786156HCID 57786156, VerbindungAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]ethanol (Reference Example 12; 183 mg, 0.419 mmol) in tetrahydrofuran (2 mL) was added diisopropylethylamine (0.11 ml, 0.629 mmol) and methanesulfonyl chloride (0.049 mL, 0.629 mmol), and the mixture was stirred at room temperature for 72 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 4-25% ethyl acetate/n-hexane gradient mixture to give the title compound (141 mg, 0.337 mmol, 80%) as an oil. The oil was crystallized from ethyl acetate-diisopropyl ether to give the title compound (73 mg, 0.174 mmol, 42%) as a colorless crystal.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 4-25% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-4373a409898d46369671edfbd3df54a0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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