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Formaldehyde → Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

HRID 1289224
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Reaktionsgleichung

Reaktionsgleichung von HRID 1289224
C=O.[F:3][C:4]1[CH:23]=[C:22]([NH:24][CH:25]2[C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][C:28]=3[CH2:27][CH2:26]2)[N:35]=[C:34]([CH3:38])[N:33]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C:32]4=[O:47])[CH:21]=[CH:20][C:5]=1[C:6]([O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19])=[O:7].[C:48]([BH3-])#N.[Na+].O>C(O)(=O)C>[F:3][C:4]1[CH:23]=[C:22]([N:24]([CH3:48])[CH:25]2[C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][C:28]=3[CH2:27][CH2:26]2)[N:35]=[C:34]([CH3:38])[N:33]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:45])[CH3:44])[C:32]4=[O:47])[CH:21]=[CH:20][C:5]=1[C:6]([O:8][C:9]1[C:10]([F:19])=[C:11]([F:18])[C:12]([F:17])=[C:13]([F:16])[C:14]=1[F:15])=[O:7]
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Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 19066345Pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

Produkt 1

HCID 19066320
Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

An aqueous solution of formaldehyde (37% weight/volume, 17.55 ml) was added dropwise during 15 minutes to a stirred solution of pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (13 g), prepared as described in Example 1, in glacial acetic acid (100 ml). The mixture was stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (1.36 g) was added portionwise during 30 minutes and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was poured onto a mixture of ice and water (500 ml) and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The product was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluant. There was thus obtained pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (11 g);

Aufarbeitung

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe product was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of hexane and ethyl acetate as eluant

Quellen und Nachweise

ORD-Eintrag
ord-437402b1b15541b4b1c2f3756e2da3c2
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05747499

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