6-(Trifluoromethyl)pyridine-3-carboxaldehyde → 2-Cyclopentyl-N-{2,6-dimethyl-4-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-phenyl}-acetamide

HRID 1820154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820154
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:17])[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:4]([CH3:18])[CH:3]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[N:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1>C(#N)C>[CH:12]1([CH2:11][C:10]([NH:9][C:5]2[C:4]([CH3:18])=[CH:3][C:2]([NH:1][CH2:27][C:24]3[CH:25]=[N:26][C:21]([C:20]([F:30])([F:19])[F:29])=[CH:22][CH:23]=3)=[CH:7][C:6]=2[CH3:8])=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 68707920N-(4-Amino-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

Produkt 1

HCID 115965852-Cyclopentyl-N-{2,6-dimethyl-4-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-phenyl}-acetamideAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

N-(4-Amino-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (204 mg) and 6-trifluoromethyl-pyridine-3-carbaldehyde (163 mg) were dissolved in acetonitrile (3 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo, redissolved in methanol (5 mL) followed by addition of acetic acid (0.5 mL) and sodium cyanoborohydride (244 mg) and stirred at 25° C. for 16 hours. Aqueous sodium carbonate (10%, 25 mL) was added, and the product was collected by filtration to furnish 0.311 g (92% yield) of the title compound as a white solid. LC-MS (m/z) 406 (MH+); tR=2.90, (UV, ELSD) 98%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.20 (m, 2H), 1.51 (m, 2H), 1.60 (m, 2H), 1.75 (m, 2H), 1.97 (s, 6H), 2.22 (m, 3H), 4.39 (d, 2H), 6.20 (t, 1H), 6.28 (s, 2H), 7.85 (d, 1H), 7.99 (d, 1H), 8.75 (s, 1H), 8.77 (s, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in methanol (5 mL)
  3. additionfollowed by addition of acetic acid (0.5 mL) and sodium cyanoborohydride (244 mg)
  4. additionAqueous sodium carbonate (10%, 25 mL) was added
  5. filtrationthe product was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9159aa530fa14b4e88771ab3f96a8528
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601870B2

Notizen zur Reaktion

Wird geladen…