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Phosphorus oxychloride → 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonamide

HRID 576799
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 576799
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:15](=[O:33])[N:16]([CH3:32])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[C:19]=3[CH3:20])=[C:12]([S:34]([OH:37])(=O)=[O:35])[CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].P(Cl)(Cl)(Cl)=O.C(C1C=CC(N2C(C3C(=O)N(C)C(=O)N(C4C=CC=C(C(F)(F)F)C=4)C=3C)=C(S(Cl)(=O)=O)C=N2)=CC=1)#[N:44].O.N>C(#N)C.C(OCC)(=O)C.O.N1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:15](=[O:33])[N:16]([CH3:32])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[C:19]=3[CH3:20])=[C:12]([S:34]([NH2:44])(=[O:37])=[O:35])[CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2]
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Komponenten

9

Edukt 4

HCID 24813Phosphorus oxychlorideHCID 12896473Azane;hydrateHCID 715138621-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acidHCID 867239071-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid chloride

Produkt 1

HCID 71251415
1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of (+)-1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid (prepared in Example 196) (2.67 g) in acetonitrile (20 ml) were added pyridine (0.81 ml) and phosphorus oxychloride (1.87 ml) and the resulting mixture was stirred at room temperature for forty five minutes. Without an isolation of the formed 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonyl chloride, the reaction solution was added dropwise to ammonia water (28%, 20 ml) that cooled to 0° C. and the resulting mixture was stirred for ten minutes. To the reaction solution were added water (40 ml) and ethyl acetate (40 ml×2) such that the intended products were extracted into an organic layer. The organic layer washed with 4% ammonia water (20 ml), saturated saline (8 ml), 1N hydrochloric acid (20 ml×2) and saturated saline (20 ml), dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford (+)-1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonamide (2.33 g). UPLC/MS 531 (M+H)/0.87 min. (measurement condition 9)

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. stirringthe resulting mixture was stirred for ten minutes
  3. extractionwere extracted into an organic layer
  4. washThe organic layer washed with 4% ammonia water (20 ml), saturated saline (8 ml), 1N hydrochloric acid (20 ml×2) and saturated saline (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1e53418e0bfa46d6aa1ebbcbd42b1ded
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040516B2

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