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

HRID 1950952

Reaktionsgleichung

Reaktionsgleichung von HRID 1950952
[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

5

Edukt 3

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 58062857cis-N-(2-Cyclobutylamino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide

Produkt 1

HCID 76683026N-[(1RS,2SR)-2-(Cyclobutyl-methyl-amino)-cyclohexyl]-2-methoxy-4,6-bis-trifluoromethyl-benzamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

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

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. customThe combined organic phases were dried on sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. 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-b6f4db8eef854930bf6f2a3d1d6f780c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404673B2

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