Benzoyl chloride → N-cyclopropyl-N-(3-(3-(neopentylamino)benzo[d]isoxazol-5-yl)benzyl)benzamide

HRID 1011452Notizen

Reaktionsgleichung

C(N(CC)CC)C.[CH:8]1([NH:11][CH2:12][C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]4[O:26][N:25]=[C:24]([NH:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:23]=4[CH:33]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:10][CH2:9]1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH:8]1([N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]4[O:26][N:25]=[C:24]([NH:27][CH2:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:23]=4[CH:33]=3)[CH:14]=2)[C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:10][CH2:9]1

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

Triethylamine (0.18 mL, 1.29 mmol, 1.5 equiv.) was added to a solution of 5-(3-((cyclopropylamino)methyl)phenyl)-N-neopentylbenzo[d]isoxazol-3-amine (exemplary compound 51) (0.30 g, 0.86 mmol, 1 equiv.) in DCM (10 mL) and the mixture was subsequently cooled to −70° C. Benzoylchloride (0.12 mL, 1.03 mmol, 1.2 equiv.) was added in drops and the mixture was slowly heated to RT and stirred for 15 hours. The reaction mixture was diluted with DCM (80 mL) and extracted with sat. aq. sodium hydrogen carbonate sol. (1×15 mL) and sat. aq. NaCl solution (1×15 mL), dried (MgSO4) and the solvent removed in a vacuum. After column-chromatographic purification (EtOAc/hexane; 10:1), the desired product (0.30 g, 77%) is obtained.

Aufarbeitung

temperaturethe mixture was slowly heated to RT
extractionextracted with sat. aq. sodium hydrogen carbonate sol. (1×15 mL) and sat. aq. NaCl solution (1×15 mL)
dry with materialdried (MgSO4)
customthe solvent removed in a vacuum
customAfter column-chromatographic purification (EtOAc/hexane; 10:1)

Quellen und Nachweise

ORD-Eintrag: ord-6643c17404e2428e954e193b8a0953f1
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07977360B2

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