Formaldehyde → N-[(1RS,2SR)-2-(Cyclobutyl-methyl-amino)-cyclohexyl]-2-methoxy-4,6-bis-trifluoromethyl-benzamide

HRID 659243

Reaktionsgleichung

[CH:1]1([NH:5][C@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[NH:12][C:13](=[O:30])[C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([C:24]([F:27])([F:26])[F:25])=[CH:16][C:15]=2[O:28][CH3:29])[CH2:4][CH2:3][CH2:2]1.C=O.[C:33](=O)([O-])[O-].[Na+].[Na+]>C(O)=O>[CH:1]1([N:5]([CH3:33])[CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]2[NH:12][C:13](=[O:30])[C:14]2[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][C:17]([C:24]([F:25])([F:26])[F:27])=[CH:16][C:15]=2[O:28][CH3:29])[CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

cis-N-(2-Cyclobutylamino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide (example 16, 118 mg, 0.27 mmol) was dissolved in 2 mL formic acid. Formaldehyde (36% in water, 0.06 mL, 0.81 mmol) was added and the reaction mixture was stirred at 110° C. over night. The reaction mixture was basified by slow addition of 10 ml 1N sodium carbonate solution. The mixture was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→110:10:1) yielded the title compound as a white solid (46 mg, 38%), MS: m/e=453.2 [(M+H)+].

Aufarbeitung

extractionThe mixture was extracted three times with ethyl acetate
customThe combined organic phases were dried on sodium sulfate
filtrationfiltered
customevaporated
customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→110:10:1)

Quellen und Nachweise

ORD-Eintrag: ord-d72662dd91784b31b702c01df00b802f
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08080541B2

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