HCID 53246296, compound → HCID 53246764, compound

HRID 1805180Notes

Reaction equation

HRID 1805180 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-8478dc5c48a843019dd4962e73ce26c5
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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