HCID 118005574, compound → HCID 118005492, compound

HRID 1478492Notes

Reaction equation

HRID 1478492 reaction equation
C([O:8][C:9]1[C:10]([O:38][CH3:39])=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][C:15]([C:20]([C:32]1[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=1)([C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1)[OH:21])=[CH:14][CH:13]=2)C1C=CC=CC=1>CO.[Pd]>[Cl:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]([OH:21])([C:32]3[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=3)[C:22]3[CH:23]=[N:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=3)[CH:16]=2)[N:11]=[C:10]([O:38][CH3:39])[C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 118005574HCID 118005574, compound2×

Product 1

HCID 118005492HCID 118005492, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3-(benzyloxy)-4-chloro-2-methoxyquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol (2.56 g, 4.61 mmol, Intermediate 11: step e) in MeOH (97 mL) was added 10% Pd/C (246 mg, 0.23 mmol). The reaction vessel was evacuated and then placed under an atmosphere of hydrogen for 1.5 hours. The mixture was then flushed with N2 and filtered through a pad of Celite®. The filtrate was concentrated to dryness, then DCM was added and the solution concentrated to dryness. The resulting solid was dried in the oven. The solid was then purified by FCC (15% MeOH/DCM) to provide the title compound.

Workup

  1. customThe reaction vessel was evacuated
  2. customThe mixture was then flushed with N2
  3. filtrationfiltered through a pad of Celite®
  4. concentrationThe filtrate was concentrated to dryness
  5. additionDCM was added
  6. concentrationthe solution concentrated to dryness
  7. customThe resulting solid was dried in the oven
  8. customThe solid was then purified by FCC (15% MeOH/DCM)

Sources & evidence

ORD record
ord-84551b3272764271b485b554e7b786ee
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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