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Hydrochloric Acid → N-[4-(1,3-benzodioxol-5-yl)-3-(2-{[5-(methylsulfonyl)-2-pyrimidinyl]oxy}ethoxy)-1H-pyrazol-5-yl]4-(tert-butyl)benzenesulfonamide

HRID 1062766
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1062766
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:31][CH2:32][CH2:33][OH:34])=[N:14][NH:15][C:16]=3[NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1.Cl[C:36]1[N:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][N:37]=1.Cl>O1CCCC1.C(OCC)(=O)C.CCOCC.CC(N(C)C)=O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:31][CH2:32][CH2:33][O:34][C:36]4[N:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][N:37]=4)=[N:14][NH:15][C:16]=3[NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:28])[CH3:29])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1
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Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 156534822-Chloro-5-methanesulfonylpyrimidine2×HCID 22281936N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]4-(tert-butyl)benzenesulfonamide

Produkt 1

HCID 9851955N-[4-(1,3-benzodioxol-5-yl)-3-(2-{[5-(methylsulfonyl)-2-pyrimidinyl]oxy}ethoxy)-1H-pyrazol-5-yl]4-(tert-butyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in oil, 20 mg) was added at 0° C. under an atmosphere of nitrogen, to a solution of N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 79) (50 mg) in a mixture of anhydrous tetrahydrofuran (3 ml) and anhydrous dimethylacetamide (0.8 ml). The reaction mixture was stirred for 10 minutes at 0° C. before a solution of 2-chloro-5-(methylsulfonyl)pyrimidine (42 mg) in anhydrous tetrahydrofuran (1 ml) was added. The reaction mixture was slowly allowed to room temperature and after 4 h, a solution of 2-chloro-5-(methylsulfonyl)pyrimidine (22 mg) in anhydrous tetrahydrofurane (0.5 ml) was added. The reaction was stirred overnight and then was poured into ether (10 ml) and an aqueous solution of HCl (1N, 10 ml). The remaining insoluble material was dissolved by the addition of ethyl acetate. The organic fraction was washed with water (twice 30 ml), brine (50 ml), dried on sodium sulfate and concentrated under reduced pressure. The yellow oil was purified by HPLC:

Aufarbeitung

  1. additionwas added
  2. washThe organic fraction was washed with water (twice 30 ml), brine (50 ml)
  3. customdried on sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe yellow oil was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0167a98b913d40cb90b70612d79040e2
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06962923B2

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