3-Fluorobenzoic Acid → HCID 53492380, compound

HRID 2045163Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:23][C:24]1[CH:25]=[C:26]([CH:30]2[C:39]([CH3:41])([CH3:40])[CH2:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([C:42]([OH:44])=[O:43])[CH:36]=3)[NH:31]2)[CH:27]=[CH:28][CH:29]=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:23][C:24]1[CH:25]=[C:26]([CH:30]2[C:39]([CH3:40])([CH3:41])[CH2:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([C:42]([OH:44])=[O:43])[CH:36]=3)[NH:31]2)[CH:27]=[CH:28][CH:29]=1)=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3-fluoro-benzoic acid (119 mg, 0.85 mmol) and 1,1′-carbonyldiimidazole (179 mg, 1.1 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 70° C. for 1 h. Then a solution of 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (200 mg, 0.68 mmol) in N,N-dimethylformamide (1.5 mL) was added and the mixture was allowed to stir at 50° C. for 3 h. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 2-[3-(3-fluoro-benzoylamino)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (40 mg, 14%) as a white solid: LC/MS m/e calcd for C25H23FN2O3 (M+H)+: 419.47, observed: 419.1.

Workup

customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

Sources & evidence

ORD record: ord-ba748709365e4188be49d93f5ca839df
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586747B2

Reaction notes

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