HCID 53246296, compound → HCID 53246764, compound

HRID 1915521Notes

Reaction equation

HRID 1915521 reaction equation
C([O:8][C:9]1[C:10]([CH:33]([CH3:35])[CH3:34])=[CH:11][C:12]([C:29]([F:32])([F:31])[F:30])=[C:13]([NH:15][C:16]([C:18]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:17])[CH:14]=1)C1C=CC=CC=1>[Pd]>[OH:8][C:9]1[C:10]([CH:33]([CH3:35])[CH3:34])=[CH:11][C:12]([C:29]([F:32])([F:30])[F:31])=[C:13]([NH:15][C:16]([C:18]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:17])[CH:14]=1

Participants

3

Reactant 1

HCID 53246296HCID 53246296, compound

Product 1

HCID 53246764HCID 53246764, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with N-[5-benzyloxy-4-isopropyl-2-(trifluoromethyl)phenyl]-4-oxo-1H-quinoline-3-carboxamide (118 mg, 0.25 mmol) and Pd/C (12 mg, 0.11 mmol) was evacuated under vacuum, followed by purging with N2. Methanol (2 mL) was added under inert atmosphere, followed by evacuating under vacuum. The reaction was stirred overnight under an atmosphere of hydrogen, filtered through a plug of celite and concentrated to give N-[5-hydroxy-4-isopropyl-2-(trifluoromethyl)phenyl]-4-oxo-1H-quinoline-3-carboxamide. 1H NMR (400.0 MHz, DMSO-d6) δ 12.93 (s, 1H), 12.59 (s, 1H), 10.29 (s, 1H), 8.87 (s, 1H), 8.32 (dd, J=1.0, 8.1 Hz, 1H), 7.95 (s, 1H), 7.83-7.74 (m, 2H), 7.52 (t, J=8.0 Hz, 1H), 7.36 (s, 1H), 3.20 (qn, J=6.9 Hz, 1H) and 1.24-1.19 (m, 6H) ppm. LC/MS: m/z 391.36 (M+H)+ at 1.77 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas evacuated under vacuum
  2. customby purging with N2
  3. additionMethanol (2 mL) was added under inert atmosphere
  4. customby evacuating under vacuum
  5. filtrationfiltered through a plug of celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d4820b400cbf46bca3235b578f6c2bee
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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