Hydrazine hydrate (1:1) → 1-[4-(5-Fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethylamine

HRID 2422888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422888
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([N:18]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:17])=[CH:12][CH:11]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.O.NN>O1CCOCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([NH2:18])[CH3:17])=[CH:12][CH:11]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 672450832-{1-[4-(5-Fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-isoindole-1,3-dione

Produkt 1

HCID 672445781-[4-(5-Fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethylamineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21966525Dioxane MethanolLösungsmittel

Versuchsvorschrift

The organic phase was washed with water, brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue chromatographed on silica gel to give to give 2-{1-[4-(5-fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-isoindole-1,3-dione (0.31 g, 0.82 mmol, 41%). To a solution of 2-{1-[4-(5-fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-isoindole-1,3-dione (0.31 g, 0.8 mmol) in dioxan/methanol (1:1, 10 ml) was added hydrazine hydrate (0.83 g, 46.5 mmol). The reaction was stirred at room temperature for 24 h. The solvent was evaporated and dichloromethane added. The resultant white solid was filtered off and dried to give 1-[4-(5-fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethylamine (0.21 g, 0.8 mmol, 100%) as a clear oil. To a solution of 1-[4-(5-fluoro-2-methoxy-pyridin-3-yl)-phenyl]-ethylamine (0.1 g, 0.4 mmol) in dichloromethane (2 ml) was added triethylamine (123 mg, 1.2 mmol) and 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonylchloride (111 mg, 0.45 mmol). The reaction mixture was agitated for 16 h and quenched with saturated aqueuos sodium bicarbonate solution. The organic phase was washed with water, brine and dried over anhydrous magneium sulfate. The residue was chromatographed on silica gel to give the title compound (42 mg, 0.1 mmol, 25%). 1H NMR (400 MHz, CDCl3): δ 8.00 (d, 1H), 7.45 (m, 3H), 7.35 (dd, 1H), 7.21 (d, 2H), 4.86 (d, 1H), 4.60 (q, 1H), 3.96 (s, 3H), 3.75 (s, 3H), 1.50 (b, 3H) ppm; MS (ESI) m/z: 459.3 [M+H]+.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additiondichloromethane added
  3. filtrationThe resultant white solid was filtered off
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2a5eb3e24d18461b8f6e6a16b5847dc5
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960365B2

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