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

HRID 2281158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281158
[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, 1 H), 8.06 (d, J=8.4 Hz, 2 H), 7.84 (d, J=7.8 Hz, 1 H), 7.80-7.75 (m, 1 H), 7.75-7.69 (m, 1 H), 7.58 (d, J=8.4 Hz, 2 H), 7.55-7.48 (m, 1 H), 5.50 (dd, J=5.0, 9.5 Hz, 1 H), 2.56 (s, 3 H), 2.24-2.14 (m, 1 H), 1.92-1.75 (m, 2 H), 1.08 (d, J=6.4 Hz, 3 H), 1.05 (d, J=6.2 Hz, 3 H).

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-dd63d37f736046c7a1611fc021e326e6
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139538B2

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