Hydrochloric Acid → Methyl 6-(4,4,4-trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinate

HRID 2173867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173867
Cl.C(OCC)C.C(OC([N:14]([CH:25]([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)[CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=1)=O)(C)(C)C>ClCCl>[F:31][C:28]([F:29])([F:30])[CH2:27][CH2:26][CH:25]([NH:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=1)[C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH:39]=[CH:40][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:43]=2)=[CH:36][CH:37]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86667303Methyl 6-(tert-butoxycarbonyl(4,4,4-trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butyl)amino)nicotinate

Produkt 1

HCID 86667304Methyl 6-(4,4,4-trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinateAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 2M solution of HCl in diethyl ether (1 mL, 2 mmol) was added to a room temperature solution of methyl 6-(tert-butoxycarbonyl(4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butyl)amino)nicotinate (30 mg, 0.051 mmol) in 1 mL dichloromethane. After 18 h, the solution was concentrated and the residue redissolved in 2 mL trifluoroacetic acid. After 2 h, the solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over MgSO4 and concentrated to give methyl 6-(4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinate (18 mg, 73%) as a colorless film. 1H NMR (400 MHz, CDCl3) 8.72-8.74 (m, 1H), 7.94 (dd, J=8 Hz, 2.5 Hz, 2H), 7.61-7.70 (m, 4H), 7.57 (d, J=8.2 Hz, 2H), 7.42 (d, J=8.2 Hz, 2H), 6.29 (d, J=8.8 Hz, 1H), 5.40 (d, J=7.6 Hz, 1H), 4.90-5.01 (m, 1H), 3.83 (s, 3H), 2.06-2.36 (m, 4H).

Aufarbeitung

  1. concentrationthe solution was concentrated
  2. dissolutionthe residue redissolved in 2 mL trifluoroacetic acid
  3. waitAfter 2 h
  4. concentrationthe solution was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9cc23665e68e43f29fd5779da4d81a6d
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056834B2

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