Hydrochloric Acid → HCID 121458877, compound

HRID 1048889Notes

Reaction equation

HRID 1048889 reaction equation
BrC1C(F)=CC(F)=C(C=1)C(Cl)=O.[F:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:36])[C:19]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:20][N:21]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:16][C:15]=1[N:37]([CH3:45])[CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1.[OH-].[Na+].Cl>O1CCOCC1>[F:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:36])[C:19]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:20][N:21]2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[CH:16][C:15]=1[N:37]([CH3:45])[CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1.[F:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:36])[C:19]([C:31]([OH:33])=[O:32])=[CH:20][N:21]2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[CH:16][C:15]=1[N:37]([CH3:45])[CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57572868HCID 57572868, compoundHCID 121447978HCID 121447978, compound

Product 2

HCID 121447978HCID 121447978, compoundHCID 121458877HCID 121458877, compoundYield 197.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 7-fluoro-1-(4-fluorophenyl)-6-(methyl(pyridin-3-ylmethyl)amino)-4-oxo-1,4-dihydroquinoline-3-carboxylate (U) was prepared from 5-bromo-2,4-difluorobenzoyl chloride via a method analogous to that described in Examples 1 and 9. Compound U (27 mg, 0.060 mmol, 1.0 eq) was dissolved in 1,4-dioxane (0.5 mL) and 1N sodium hydroxide (0.12 mL, 0.12 mmol, 2.0 eq) was added. The reaction was stirred until complete by LCMS, at which time it was neutralized to pH 4-5 with 1N HCl and concentrated to dryness. The residue was suspended in 10% methanol in DCM and filtered. The organics were concentrated to afford 25 mg (99%) of the title compound as an off-white solid that was used without further purification. ES-MS [M+1]+: 422.2.

Workup

  1. concentrationconcentrated to dryness
  2. filtrationfiltered
  3. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-c9b3ddd1648246b680c64d43e964ef01
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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