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

HRID 2281158Notes

Reaction equation

HRID 2281158 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dd63d37f736046c7a1611fc021e326e6
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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