N-Iodosuccinimide → N-cyclopentyl-8-iodo-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

HRID 1296722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296722
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=[C:11]3[N:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:22]N1C(=O)CCC1=O>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:15]([I:22])=[C:11]3[N:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 69447864N-cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

Produkt 1

HCID 69447640N-cyclopentyl-8-iodo-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N-Cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4amine (0.25 g, 0.90 mmol) was dissolved in dichlorornethane. To this solution was added N-iodosuccinimide (300 mg, 1.33 mmol) and the resulting solution was stirred at room temperature for 30 minutes. Additional dichloromethane was added and the reaction mixture was extracted with 1N aqueous sodium hydroxide and with water. The organic phase was dried (magnesium sulfate), filtered and concentrated to give a solid. This solid was purified by silica gel chromatography (ethyl acetate:hexane 1:1) to give 310 mg (85%) of N-cyclopentyl-8-iodo-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine as a yellow solid. 1H-NMR (CDCl3): δ 8.35 (s, 1H), 7.98 (m, 2H), 7.55 (m, 3H), 6.64 (d, 1H), 4.60 (m, 1H), 2.3–2.1 (m, 2H), 2.0–1.6 (m, 6H); MS m/z 406 (M+1).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with 1N aqueous sodium hydroxide and with water
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid
  6. customThis solid was purified by silica gel chromatography (ethyl acetate:hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-a99ba0b9b9694940bdfd17c5c2a1455f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07247626B2

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