Dimethyl Sulfoxide → o-Fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoic acid

HRID 1289222

Reaktionsgleichung

Reaktionsgleichung von HRID 1289222
Br[CH:2]1[C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:5]=2[CH2:4][CH2:3]1)[N:12]=[C:11]([CH3:15])[N:10]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]3=[O:24].CC([NH3+])(C)CO.[NH2:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([O-:38])=[O:37])=[C:34]([F:41])[CH:33]=1.C(=O)([O-])[O-].[Ca+2].CS(C)=O>O>[F:41][C:34]1[CH:33]=[C:32]([NH:31][CH:2]2[C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][C:5]=3[CH2:4][CH2:3]2)[N:12]=[C:11]([CH3:15])[N:10]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]4=[O:24])[CH:40]=[CH:39][C:35]=1[C:36]([OH:38])=[O:37]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 10112Calcium CarbonateHCID 105246016-bromo-2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-oneHCID 131720633p-Amino-o-fluorobenzoic acid 1,1-dimethyl-2-hydroxyethylammonium salt

Produkt 1

HCID 19066365o-Fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one (26 g), p-amino-o-fluorobenzoic acid 1,1-dimethyl-2-hydroxyethylammonium salt (42 g), calcium carbonate (21.4 g) and DMSO (200 ml) was stirred at ambient temperature for 72 hours. The mixture was poured onto a mixture of ice and water (1 liter). The precipitate was isolated, washed with water and dried under vacuum. The product was purified by column chromatography using initially a 9:1 mixture of methylene chloride and methanol and then a 9:1:0.1 mixture of methylene chloride, methanol and acetic acid as eluant. There was thus obtained o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoic acid as a gum (20 g).

Aufarbeitung

  1. customThe precipitate was isolated
  2. washwashed with water
  3. customdried under vacuum
  4. customThe product was purified by column chromatography
  5. additiona 9:1 mixture of methylene chloride and methanol
  6. additiona 9:1:0.1 mixture of methylene chloride, methanol and acetic acid as eluant

Quellen und Nachweise

ORD-Eintrag
ord-569c7e2cab5f4a62929158546ea5e837
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05747499

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