Dichloromethane → (3-(4-(1H-Pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone

HRID 926480Notes

Reaction equation

HRID 926480 reaction equation
[N:1]1([C:6]2[CH:34]=[CH:33][C:9]([CH2:10][C:11]3[C:12]([O:31][CH3:32])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([CH:22]([C:24]3[N:28]([CH3:29])[C:27]([CH3:30])=[N:26][CH:25]=3)[OH:23])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.ClCCl>O1CCOCC1.[O-2].[O-2].[Mn+4]>[N:1]1([C:6]2[CH:34]=[CH:33][C:9]([CH2:10][C:11]3[C:12]([O:31][CH3:32])=[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])[C:27]([CH3:30])=[N:26][CH:25]=3)=[O:23])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 118005895(3-(4-(1H-Pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol

Product 1

HCID 118006101(3-(4-(1H-Pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

A heterogeneous mixture of (3-(4-(1H-pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol (625 mg, 1.32 mmol, Intermediate 21: step a) and manganese dioxide (809 mg, 7.91 mmol) in dioxane (13 mL) was heated to 100° C. After 135 minutes, the flask was allowed to cool to 23° C. Dichloromethane (40 mL) was added and the mixture was filtered through Celite®, rinsing with dichloromethane. Silica gel (3 g) was added to the filtrate and the solvent was removed by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a column of silica gel for purification. Elution with 30% ethyl acetate-hexanes initially, grading to 100% ethyl acetate provided the title compound as an off-white solid.

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. washrinsing with dichloromethane
  3. additionSilica gel (3 g) was added to the filtrate
  4. customthe solvent was removed by rotary evaporation
  5. customto afford a free-flowing powder
  6. customThe powder was loaded onto a column of silica gel for purification
  7. washElution with 30% ethyl acetate-hexanes initially

Sources & evidence

ORD record
ord-1ec32aaa34494dca82dfab8c115b5787
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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