Dimethylformamide → HCID 131715264, Verbindung

HRID 1904844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904844
Br[CH2:2][CH2:3][O:4][C:5]1[N:9]([CH3:10])N=NN=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35]CN)[CH2:31][CH2:30]2)=[CH:14][CH:13]=1.[C:38](=[O:41])([O-:40])[O-:39].[Na+].[Na+].CN(C)C=[O:47]>O>[C:5]([OH:4])(=[O:47])[C:38]([OH:40])=[O:41].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:10][N:9]3[CH2:2][CH2:3][O:4][C:5]3=[O:39])[CH2:31][CH2:30]2)=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 14518041HCID 14518041, VerbindungHCID 14518104HCID 14518104, Verbindung

Produkt 1

HCID 131715264HCID 131715264, VerbindungAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4 parts of 5-(2-bromoethoxy)-1-methyl-1H-tetrazole, 5.5 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimdazol-2-yl]methyl]-1-piperdineethanamine, 2.3 parts of sodium carbonate and 45 parts of N,N-dimethylformamide was stirred overnight at 70° C. The reaction mixture was poured into water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in ethanol. The salt was filtered off and dried, yielding 1.3 parts (13%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]2-oxazolidinone ethanedioate(2:5); mp. 147.9° C. (385).

Aufarbeitung

  1. extractionThe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ad7e28d4606946e0bc9353ce7e133d66
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04839374

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