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Triethylamine → 6-(3-fluoro-pyridin-4-yl)-3-methyl-2-((3S)-3-(4-piperidin-1-yl-phenyl)-piperazin-1-yl)-3H-pyrimidin-4-one trihydrochloride

HRID 1091393
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1091393
[ClH:1].Cl.Cl.[N:4]1([C:10]2[CH:15]=[CH:14][C:13]([C@H:16]3[CH2:21][NH:20][CH2:19][CH2:18][NH:17]3)=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[Cl:29][C:30]1[N:35]([CH3:36])[C:34](=[O:37])[CH:33]=[C:32]([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][C:39]=2[F:44])[N:31]=1>O1CCCC1>[ClH:29].[ClH:1].[ClH:29].[F:44][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][C:38]=1[C:32]1[N:31]=[C:30]([N:20]2[CH2:19][CH2:18][NH:17][C@@H:16]([C:13]3[CH:12]=[CH:11][C:10]([N:4]4[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]4)=[CH:15][CH:14]=3)[CH2:21]2)[N:35]([CH3:36])[C:34](=[O:37])[CH:33]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 595768122-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-oneHCID 66594480(2S)-2-(4-piperidin-1-yl-phenyl)-piperazine trihydrochloride

Produkt 1

HCID 665947026-(3-fluoro-pyridin-4-yl)-3-methyl-2-((3S)-3-(4-piperidin-1-yl-phenyl)-piperazin-1-yl)-3H-pyrimidin-4-one trihydrochlorideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of (2S)-2-(4-piperidin-1-yl-phenyl)-piperazine trihydrochloride obtained in Reference Example 3 (199 mg, 0.561 mmol) and triethylamine (427 μl, 306 mmol) in tetrahydrofuran was refluxed for 15 minutes. After cooling to room temperature, 2-chloro-6-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (122 mg, 0.510 mmol) was added portionwise and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane and aqueous sodium bicarbonate, and the solution was passed through CHEM ELUT CE1010 (manufactured by VARIAN). The filtrate was concentrated, and the resulting residue was washed with diethyl ether. Hydrogen chloride in ethyl acetate (4N) was added to a solution of the resulting solids in ethyl acetate, and the precipitate was collected by the filtration and dried to furnish 6-(3-fluoro-pyridin-4-yl)-3-methyl-2-((3S)-3-(4-piperidin-1-yl-phenyl)-piperazin-1-yl)-3H-pyrimidin-4-one trihydrochloride (267 mg, 0.479 mmol, 94%) as pale yellow powder.

Aufarbeitung

  1. temperaturewas refluxed for 15 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. concentrationThe filtrate was concentrated
  5. washthe resulting residue was washed with diethyl ether
  6. additionHydrogen chloride in ethyl acetate (4N) was added to a solution of the resulting solids in ethyl acetate
  7. filtrationthe precipitate was collected by the filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8b17f722656f41148cb6734eaac4bf36
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129377B2

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