Sodium Methoxide → (3-(4-(1H-Pyrazol-1-yl)benzyl)-4-chloro-2-methoxy-8-methylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 1507313Notes

Reaction equation

HRID 1507313 reaction equation
[N:1]1([C:6]2[CH:33]=[CH:32][C:9]([CH2:10][C:11]3[C:12](Cl)=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([C:22]([C:24]3[N:28]([CH3:29])[CH:27]=[N:26][CH:25]=3)=[O:23])=[CH:16][C:15]=4[CH3:30])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:34][O-:35].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[N:1]1([C:6]2[CH:33]=[CH:32][C:9]([CH2:10][C:11]3[C:12]([O:35][CH3:34])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([C:22]([C:24]3[N:28]([CH3:29])[CH:27]=[N:26][CH:25]=3)=[O:23])=[CH:16][C:15]=4[CH3:30])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 118005956(3-(4-(1H-Pyrazol-1-yl)benzyl)-2,4-dichloro-8-methylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

Product 1

HCID 118005990(3-(4-(1H-Pyrazol-1-yl)benzyl)-4-chloro-2-methoxy-8-methylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3-(4-(1H-pyrazol-1-yl)benzyl)-2,4-dichloro-8-methylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone (1.05 g, 2.20 mmol, Intermediate 14: step a) and dry sodium methoxide (0.59 g, 11.02 mmol) in toluene (10 mL) was heated in a sealed tube at 110° C. for 12 hours. The mixture was cooled to room temperature, diluted with DCM, stirred for 30 minutes at room temperature and the resulting suspension filtered through Celite®, rinsing several times with DCM. The solvents were removed under reduced pressure and the residue chromatographed (DCM/10% MeOH in DCM, gradient) to provide the crude product. Recrystallization from MeOH, filtering and drying under reduced pressure overnight provided the title compound.

Workup

  1. filtrationthe resulting suspension filtered through Celite®
  2. washrinsing several times with DCM
  3. customThe solvents were removed under reduced pressure
  4. customthe residue chromatographed (DCM/10% MeOH in DCM, gradient)
  5. customto provide the crude product
  6. customRecrystallization from MeOH
  7. filtrationfiltering
  8. customdrying under reduced pressure overnight

Sources & evidence

ORD record
ord-1544644dbeae4a538514a289247062e3
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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