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Thionyl Chloride → HCID 57593710, Verbindung

HRID 1785331
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1785331
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:4])=[O:3].S(Cl)(Cl)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]2[N:34]=[C:33]([NH:35][CH2:36][CH2:37][C:38]3[NH:39][CH:40]=[N:41][CH:42]=3)[C:32]([Br:43])=[CH:31][N:30]=2)=[CH:24][CH:23]=1>CC(N(C)C)=O>[Br:43][C:32]1[C:33]([NH:35][CH2:36][CH2:37][C:38]2[NH:39][CH:40]=[N:41][CH:42]=2)=[N:34][C:29]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:9](=[O:11])[C:8]3[CH:12]=[CH:13][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=3)=[CH:27][CH:26]=2)=[N:30][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 27238714-(Methanesulfonyl)-3-nitrobenzoic acidHCID 57593472N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamine

Produkt 1

HCID 57593710HCID 57593710, VerbindungAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374
Dimethylacetamide
Lösungsmittel

Versuchsvorschrift

4-Methanesulfonyl-3-nitro-benzoic acid (72 mg, 0.29 mmole) was dissolved in DMA (3 ml) and thionyl chloride (0.29 mmole) was added at ambient temperature. After the mixture was stirred for 5 minutes N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (100 mg, 0.26 mmole, prepared according to procedure 21) was added and the reaction was allowed to stir overnight. After extraction with bicarbonate solution and ethyl acetate (3×) the combined organic layers were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by flashmaster chromatography on silica gel to provide 37 mg of N-(4-{5-Bromo-4-[2-(3H-imidazol-4-yl)-ethylamino]-pyrimidin-2-ylamino}-phenyl}-4-methanesulfonyl-3-nitro-benzamide (23% yield). ESI-MS: 602.

Aufarbeitung

  1. additionwas added
  2. extractionAfter extraction with bicarbonate solution and ethyl acetate (3×) the combined organic layers
  3. dry with materialwere dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flashmaster chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7374dfe2c0c34fff95de0663074bc577
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07504410B2

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