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Potassium Iodide → HCID 13769740, Verbindung

HRID 979929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 979929
Cl[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[N:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[N:22]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[F:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:29]2[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[N:22]=[C:21]2[NH:20][CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][NH:11][C:2]3[N:6]([CH3:7])[CH:5]=[N:4][C:3]=3[N+:8]([O-:10])=[O:9])[CH2:15][CH2:16]2)=[CH:32][CH:33]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 210105-Chloro-1-methyl-4-nitroimidazoleHCID 13588034HCID 13588034, Verbindung

Produkt 1

HCID 13769740HCID 13769740, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1.62 parts of 5-chloro-1-methyl-4-nitro-1H-imidazole, 3.67 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-3-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine, 1.1 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was cooled and poured onto water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 2.2 parts (45%) of 3-[(4-fluorophenyl)methyl]-N-[1-[2-[(1-methyl-4-nitro-1H-imidazol-5-yl)amino]ethyl]-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine; mp. 198.7° C. (compound 11 ).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. extractionThe product was extracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-f5f5de2a839642bc84dc31a6ccd887a9
Quelldatensatz
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04634704

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