Hydrochloric Acid → HCID 178522932, compound

HRID 2289950Notes

Reaction equation

HRID 2289950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([F:23])=[C:17]([F:24])[C:16]=3F)=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[O:28]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]1.Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([F:23])=[C:17]([F:24])[C:16]=3[O:34][CH:31]2[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 74956Tetrahydro-4H-pyran-4-olHCID 178522923HCID 178522923, compound

Product 1

HCID 178522932HCID 178522932, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

N-((4-Chlorophenyl)methyl)-4-hydroxy-6,7,8-trifluoro-3-quinolinecarboxamide (366 mg) from Example No. 15 and sodium hydride (60% dispersion, 40 mg) are dissolved in DMF (10 mL) and to the mixture is added tetrahydro-2H-pyran-4-ol (114 μL). Additional sodium hydride (60 mg) is added and the mixture is heated at 140° C. for 1 h. The reaction mixture is allowed to cool to rt, poured into water (30 mL), acidified with 1 N hydrochloric acid (20 mL), and extracted with ethyl acetate (3×25 mL). The organic layer is washed with brine (10 mL), dried (MgSO4), and concentrated. The resulting solid is triturated with heptane (10 mL) and filtered to afford 153 mg of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. washThe organic layer is washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting solid is triturated with heptane (10 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-78e63875f99f45b9ad0b125f03d2e904
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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