Acetic Acid → 2-Cyclopentyl-N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide

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Reaktionsgleichung

[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:12][C:11]=2[CH3:29])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30](O)(=O)C.C([BH3-])#N.[Na+].C=O>CO>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([N:17]([CH3:30])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=3)=[CH:12][C:11]=2[CH3:29])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To 2-cyclopentyl-N-[2,6-dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide (4k, 150 mg) dissolved in methanol (20 mL) and acetic acid (2 mL) were added sodium cyanoborohydride (175 mg) and formaldehyde (200 uL) and the reaction mixture was stirred at 25° C. for 70 minutes. The reaction was quenched with saturated aqueous sodium bicarbonate and the product collected by filtration to furnish 151 mg (97% yield) of the title compound as a white solid. LC-MS (m/z) 419 (MH+); tR=3.39, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.20 (m, 2H), 1.51 (m, 2H), 1.61 (m, 2H), 1.75 (m, 2H), 2.02 (s, 6H), 2.24 (m, 3H), 2.97 (s, 3H), 4.63 (s, 2H), 6.42 (s, 2H), 7.41 (d, 2H), 7.68 (d, 2H), 8.83 (s, 1H).

Aufarbeitung

customThe reaction was quenched with saturated aqueous sodium bicarbonate
filtrationthe product collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-8b8a393a11444f28b76bdbfa5c946a15
Quelldatensatz: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07601870B2

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