Dimethylcarbamoyl Chloride → 5-((4-(Propargyl)piperidin-1-yl)methyl)quinolin-8-yl dimethylcarbamate

HRID 2403465

Reaktionsgleichung

[H-].[Na+].C#CCN1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]3[C:14]=2[CH:15]=[CH:16][CH:17]=[N:18]3)[CH2:8][CH2:7]1.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27]>C1COCC1>[CH3:24][N:25]([CH3:29])[C:26](=[O:27])[O:23][C:20]1[CH:21]=[CH:22][C:13]([CH2:12][N:9]2[CH2:8][CH2:7][CH:15]([CH2:14][C:13]#[CH:12])[CH2:11][CH2:10]2)=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a suspension of NaH (24 mg, 0.6 mmol 1.2 equiv) in anhydrous THF, HLA20 (140 mg, 0.5 mmol, 1.0 equiv) was added under Ar at 0° C. The resulting mixture was stirred for 20 min at 0° C. A solution of dimethyl carbamoyl chloride (1.1 equiv) in anhydrous THF was added, and the stirring was continued for 24 h at room temperature. After evaporation of the solvent, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried with NaSO4. Evaporation of the solvent gave a crude product that was purified by RP HPLC.

Aufarbeitung

additionwas added under Ar at 0° C
waitthe stirring was continued for 24 h at room temperature
customAfter evaporation of the solvent, water
additionwas added
extractionthe resulting mixture was extracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried with NaSO4
customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag: ord-e7f96697f09a4939978d60fabfd9c626
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08802675B2

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