Trifluoroacetic acid → (+/-)-4-(3-Methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid trifluoroacetic acid salt

HRID 1424287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424287
[CH3:1][CH:2]([CH3:30])[CH2:3][CH:4]([C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[CH:19][CH:18]=1)[NH:5][C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH3:1][CH:2]([CH3:30])[CH2:3][CH:4]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:28][CH:29]=1)[NH:5][C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71243814Tert-butyl (+/-)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate

Produkt 1

HCID 86718841(+/-)-4-(3-Methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid trifluoroacetic acid salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl(+/−)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate (325 mg, 0.803 mmol) in dichloromethane (8.0 mL) was added trifluoroacetic acid (0.62 mL, 8.0 mmol). The solution was stirred at room temperature for 17 hours then concentrated under reduced pressure. Toluene (3 mL) was added, and the solution was again concentrated under reduced pressure to remove excess trifluoroacetic acid to give (+/−)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid trifluoroacetic acid salt as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.26 (s, 1H), 8.06 (d, J=8.4 Hz, 2H), 7.84 (d, J=7.8 Hz, 1H), 7.80-7.75 (m, 1H), 7.75-7.69 (m, 1H), 7.58 (d, J=8.4 Hz, 2H), 7.55-7.48 (m, 1H), 5.50 (dd, J=5.0, 9.5 Hz, 1H), 2.56 (s, 3H), 2.24-2.14 (m, 1H), 1.92-1.75 (m, 2H), 1.08 (d, J=6.4 Hz, 3H), 1.05 (d, J=6.2 Hz, 3H).

Aufarbeitung

  1. concentrationthen concentrated under reduced pressure
  2. additionToluene (3 mL) was added
  3. concentrationthe solution was again concentrated under reduced pressure
  4. customto remove excess trifluoroacetic acid

Quellen und Nachweise

ORD-Eintrag
ord-875c346a82be411782c9a97a707c7eff
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927577B2

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