Hydrochloric Acid → HCID 67215759, compound

HRID 1969439Notes

Reaction equation

HRID 1969439 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([CH:24]=[O:25])[CH:21]=[N:20]2)=[CH:15][CH:14]=1.C[Si](C)(C)[C:34]([F:37])([F:36])[F:35].[F-].[Cs+].Cl>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([CH:24]([OH:25])[C:34]([F:37])([F:36])[F:35])[CH:21]=[N:20]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86654210HCID 86654210, compound

Product 1

HCID 67215759HCID 67215759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 5-fluoro-1-[4-[4-formyl-1H-pyrazol-1-yl)benzyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.100 g, 0.238 mmol) in 2 mL of dichloromethane was added trimethyl(trifluoromethyl)silane (0.045 g, 0.25 mmol) and cesium fluoride (3.6 mg, 0.024 mmol). After 3 hours, 4 N HCl (0.36 mL, 1.4 mmol) was added. After 1 hour, the reaction mixture was diluted with an additional 20 mL dichloromethane and washed with water and brine. The organic extracts were dried, filtered and concentrated in vacuo to provide the title compound (crude) which gave a mass ion (ES+) of 489.9 for M+H+. This compound could be further hydrolyzed to the corresponding carboxylic acid, as described in Example 1.

Workup

  1. waitAfter 1 hour
  2. washwashed with water and brine
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5da8df854774ac297f1e54f151ca2eb
Source dataset
uspto-grants-2013_04
Patent number
US08426598B2

Reaction notes

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