Sodium Carbonate → HCID 178432405, Verbindung

HRID 1614175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614175
Br.Br[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH2:12][CH2:13][S:14][C:8]2=[N:7][C:6]=1[CH3:15].Cl.Cl.[F:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:24][NH:25]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[F:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH:28]3[CH2:33][CH2:32][N:31]([CH2:3][CH2:4][C:5]4[C:10](=[O:11])[N:9]5[CH2:12][CH2:13][S:14][C:8]5=[N:7][C:6]=4[CH3:15])[CH2:30][CH2:29]3)=[N:24][NH:25]2)=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 155864646-(2-bromoethyl)-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromideHCID 1784786406-fluoro-3-(4-piperidinyl)-1H-indazole dihydrochloride

Produkt 1

HCID 178432405HCID 178432405, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 4.4 parts of 6-(2-bromoethyl)-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide, 3.7 parts of 6-fluoro-3-(4-piperidinyl)-1H-indazole dihydrochloride, 4.25 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone was stirred for 6 hours at reflux temperature. After cooling, the reaction mixture was filtered, The precipitate was stirred in water and the whole was filtered again. The precipitated product was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2.5 parts (48.3%) of 6-[2-[4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]ethyl]-2,3-dihydro-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 207.6° C. (compound 2).

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. stirringThe precipitate was stirred in water
  5. filtrationthe whole was filtered again
  6. customThe precipitated product was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from 2-propanol
  11. filtrationThe product was filtered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0e7624c93df34d4a85fe64e93e414aa5
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196425

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