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Pyridine → HCID 22398447, Verbindung

HRID 912605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 912605
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[N:11]=[C:10]([NH:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[N:9]=1.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:32][CH2:33][C:34]([NH:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[N:11]=[C:10]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=2)[N:9]=1)=[O:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6577Chloroacetyl chloride2×HCID 486363HCID 486363, Verbindung

Produkt 1

HCID 22398447HCID 22398447, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Pyridine (1 ml) was added to a mixture of 4-[[4-amino-6-[(2,6-dichloro-phenyl)-methyl]-2-pyrimidinyl]amino]benzonitrile (0.00135 mol) in CH2Cl2 (19 ml). A solution of chloroethanoyl chloride (0.001375 mol) in CH2Cl2 (0.5 ml) was added dropwise on an ice bath. The mixture was stirred at room temperature for 2 hours. More chloroethanoyl chloride (0.00625 mol) in CH2Cl2 (0.5 ml) was added. The mixture stood in the refrigerator overnight. The solvent was evaporated. The residue was treated with a saturated Na2CO3 solution and the mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and concentrated. The residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.1). The desired fractions were collected and the solvent was evaporated, yielding 0.22 g (36.5%) of 2-chloro-N-[6-[(2,6-dichloro-phenyl)methyl]-2-[(4-cyano-phenyl)amino]-4-pyrimidinyl]acetamide (interm. 13).

Aufarbeitung

  1. customstood in the refrigerator overnight
  2. customThe solvent was evaporated
  3. additionThe residue was treated with a saturated Na2CO3 solution
  4. extractionthe mixture was extracted with CH2Cl2
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.1)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7c2b5b908ea04fe0af1db902bd9fbf9c
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08026248B2

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