Ammonium Chloride → 1-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-6-ylamine

HRID 1790123

Reaktionsgleichung

Reaktionsgleichung von HRID 1790123
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[N:15]1([CH2:14][CH2:13][N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=3)[CH:8]=[N:9]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 220366146-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Produkt 1

HCID 112762881-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-6-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A mixture of 6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (1.60 g, 6.15 mmol), iron powder (3.40 g, 60.8 mmol), and ammonium chloride (166 mg, 3.13 mmol) in a 4:1 solution of ethanol/H2O was heated to reflux for 3 hours, cooled to room temperature, concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes, filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4), and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.66 (m, 4H), 2.50 (m, 4H), 2.85 (t, 2H, J=6.78), 4.27 (t, 2H, J=6.78), 5.30 (s, 2H), 6.49 (m, 2H), 7.35 (m, 1H), 7.70 (m, 1H); MS (DCI/NH3) m/z 231 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica gel which
  5. washwas rinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2d6d0e1abd944ea5bfa1cc44b1187f2d
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071182B2

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