Hydrochloric Acid → N-(4-oxo-2-(3-(trifluoromethyl)phenyl)-1,4-dihydroquinolin-8-yl)pyrazine-2-carboxamide

HRID 520464Notes

Reaction equation

HRID 520464 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)=[O:17])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH:6]=1)(=O)C.Cl>C1COCC1.[OH-].[Na+]>[O:4]=[C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)=[O:17])[CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[CH:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 585528388-(Pyrazine-2-carboxamido)-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate

Product 1

HCID 45254177N-(4-oxo-2-(3-(trifluoromethyl)phenyl)-1,4-dihydroquinolin-8-yl)pyrazine-2-carboxamideYield 70.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 8-(pyrazine-2-carboxamido)-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate 41 (33 mg, 0.073 mmol) in THF (2 mL) and 1N NaOH (0.5 mL) was heated at 60° C. for 48 h. The reaction mixture was cooled to room temperature and 1N HCl (5 mL) was added. The resulting precipitate was collected by filtration, rinsed with 3 mL H2O, and dried under vacuum to give Compound 409 (21 mg, 70% yield). MS (ESI) calc. for C21H13F3N4O2: 410.10. found: 411 [M+H].

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washrinsed with 3 mL H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-1e82f96d9e9d4f7cae61b0802f997353
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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