Water → HCID 178521738, Verbindung

HRID 1768568Notizen

Reaktionsgleichung

[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:19]3[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH2:7][CH2:6]1.[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([N:30]=[C:31]=[O:32])=[CH:24][C:23]=2[O:22]1.O.CCOCC>CN(C=O)C>[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([NH:30][C:31]([O:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][CH:8]([C:11]4[C:19]5[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=5)[NH:13][N:12]=4)[CH2:7][CH2:6]3)=[O:32])=[CH:24][C:23]=2[O:22]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A solution of 3-[1-(1-hydroxyprop-3-yl)-4-piperidinyl]-6-fluoro-1H-indazole (230 mg, 0.83 mmol) in 5 ml dry DMF was added 3,4-methylenedioxyphenylisocyanate (291 mg, 1.65 mmol) in 3 ml dry DMF. The reaction was heated to 100° C. for 2 h and 16 h at 80° C. The reaction was cooled to room temperature and added a mixture of 50 ml water and 200 ml ether, filtered and separated. The ether phase was washed with water, brine and dried with sodium sulphate and concentrated in vacuo. The crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1, v/v). Concentration of the appropriate fractions afforded 50 mg (11%) of the title compound as an amorphous solid.

Aufarbeitung

temperatureThe reaction was cooled to room temperature
additionadded
filtrationfiltered
customseparated
washThe ether phase was washed with water, brine
dry with materialdried with sodium sulphate
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1

Quellen und Nachweise

ORD-Eintrag: ord-10eb26b267f447b0afe3327c0c073b53
Quelldatensatz: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05378714

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