3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole → 3-{2-[4-(6-Fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-vinyl}-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one

HRID 1271536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271536
[CH3:1][C:2]1[N:3]=[C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][N:5]2[C:6](=[O:11])[C:7]=1[CH2:8][CH:9]=O.[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1>C1(C)C=CC=CC=1>[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:25][CH2:26][N:27]([CH:9]=[CH:8][C:7]4[C:6](=[O:11])[N:5]5[CH2:12][CH2:13][CH2:14][CH2:15][C:4]5=[N:3][C:2]=4[CH3:1])[CH2:28][CH2:29]3)=[N:22][O:23][C:19]=2[CH:18]=1

Komponenten

4

Edukt 2

HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 102144672-(2-Methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)acetaldehyde

Produkt 1

HCID 865989853-{2-[4-(6-Fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-vinyl}-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-oneAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2.96 g (14.33 mmoles) of (2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)-acetaldehyde (II), 3.16 g (14.33 mmoles) of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (IV) and 50 mL of toluene was transferred to a Dean Stark apparatus. The mixture was brought to boiling point, refluxed for 3 hours, and the solvent was evaporated under reduced pressure to give 5.70 g (97.3%) of 3-{2-[4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-vinyl}-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one (III) as a deep orange solid. The compound thus obtained was pure enough as to be used in the subsequent reaction step with no prior purification or optionally crystallized from an organic solvent, preferably ethanol.

Aufarbeitung

  1. temperaturerefluxed for 3 hours
  2. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-74beb3eedc224da1a6161a1fe29467c7
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205405B2

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