Trichloroacetyl chloride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 900254

Reaktionsgleichung

[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)[CH:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC.ClC(Cl)(Cl)[C:27](Cl)=[O:28].Cl.Cl.[CH:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]1)([CH3:36])[CH3:35]>C(Cl)Cl>[CH:34]([N:37]1[CH2:42][CH2:41][CH:40]([NH:43][C:27]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[CH:17]=[CH:16][N:15]=2)=[O:28])[CH2:39][CH2:38]1)([CH3:36])[CH3:35]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 5-(5-Chloro-thiophen-2-yl)-3-imidazol-1-ylmethyl-isoxazole (85 mg) and NEt3 (89 μL) in DCM (3 mL) was added trichloroacetyl chloride (43 μL) dropwise at 0° C. The mixture was stirred for 5 min at 0° C. and for 30 min at RT. More NEt3 (133 μL) and 1-isopropyl-piperidin-4-ylamine dihydrochloride (88 mg) were added and stirring was continued for 2 h at RT. The mixture was concentrated and the residue was purified by preparative HPLC. The fractions containing the product were evaporated to provide 67 mg of the title compound as its trifluoroacetate salt. MS (ESI+): mi/e=434, chloro pattern.

Aufarbeitung

stirringstirring
waitwas continued for 2 h at RT
concentrationThe mixture was concentrated
customthe residue was purified by preparative HPLC
additionThe fractions containing the product
customwere evaporated

Quellen und Nachweise

ORD-Eintrag: ord-855567cfc5f248899cc0bf9c88d2e0b3
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07358268B2

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