Acetic Acid → {4-[({3-[3-Benzoyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenyl}Amino)Methyl]Phenyl}Acetic Acid

HRID 2104515Notes

Reaction equation

[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36]C)=[O:35])=[CH:29][CH:28]=3)[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:38]([F:41])([F:40])[F:39])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].C(O)(=O)C>C1COCC1.CO.O>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:31][CH:32]=3)[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:38]([F:39])([F:40])[F:41])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate (0.06 g, 0.11 mmol) in THF/methanol/water (2:1:1, 10 mL) was added lithium hydroxide monohydrate (0.06 g, 1.4 mmol). The reaction was stirred at 40° C. for 1 h. The reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and dried over P2O5 to give the title compound as an orange solid (0.05 g, 93%): MS (EI) m/z 541.3 (M+H)+; 1H NMR (DMSO-d6): δ 3.53 (s, 2H), 4.12 (d, J=5.8 Hz, 2H), 6.35-6.55 (m, 4H), 6.97 (t, J=7.4 Hz, 1H), 7.15-7.22 (m, 4H), 7.36 (t, J=7.8 Hz, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.61 (d, J=8.2 Hz, 2H), 7.72 (t, J=8.0 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 8.29 (d, J=7.1 Hz, 1H), 9.08 (s, 1H).

Workup

customthe solid was collected
dry with materialdried over P2O5

Sources & evidence

ORD record: ord-50e5c8159fe9475780d8e093c41a956f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Reaction notes

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