Ethanesulfonic acid → n-{2-Tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1h-benzimidazol-5-yl}ethanesulfonamide esylate

HRID 230717

Reaktionsgleichung

Reaktionsgleichung von HRID 230717
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:29]([S:31]([OH:34])(=[O:33])=[O:32])[CH3:30]>C(OC)(C)(C)C>[S:31]([CH2:29][CH3:30])([OH:34])(=[O:33])=[O:32].[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:12][CH2:13][C:14]([F:18])([F:17])[CH2:15][CH2:16]2)[C:8]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH2:27][CH3:28])(=[O:25])=[O:26])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 11668Ethanesulfonic acidHCID 11675994Ethanesulfonamide, N-(1-((4,4-difluorocyclohexyl)methyl)-2-(1,1-dimethylethyl)-1H-benzimidazol-5-yl)-

Produkt 1

HCID 16742587n-{2-Tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1h-benzimidazol-5-yl}ethanesulfonamide esylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

N-{2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}ethanesulfonamide (111 mg) was slurried in methyl tert-butyl ether (2.1 ml) at 48° C. and ethane sulphonic acid (23 μl, 95%) was added. Shortly after the slurry became thinner and then recrystallised into a thicker slurry which was left over night at room temperature. The resulting crystals were filtered off, washed with methyl tert-butyl ether (2×400 μl) and dried at 40° C. under vacuum. A total of 105 mg (yield 75%) crystalline N-{2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}ethanesulfonamide esylate was obtained.

Aufarbeitung

  1. customrecrystallised into a thicker slurry which
  2. waitwas left over night at room temperature
  3. filtrationThe resulting crystals were filtered off
  4. washwashed with methyl tert-butyl ether (2×400 μl)
  5. customdried at 40° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-240d4f8e088747f9be62236267c2a75b
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566788B2

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