HCID 59436026, compound → HCID 59435994, compound

HRID 1802483Notes

Reaction equation

HRID 1802483 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12]2[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]3[CH:23]=[C:24]([Br:27])[CH:25]=[CH:26][C:14]=3[N:13]=2)=[C:6]([Cl:28])[CH:5]=1)(=[O:3])[CH3:2].[CH3:29][Mg]Br>C1COCC1>[Br:27][C:24]1[CH:25]=[CH:26][C:14]2[N:13]=[C:12]([NH:11][C:7]3[C:6]([Cl:28])=[CH:5][C:4]([C:1]([OH:3])([CH3:29])[CH3:2])=[CH:9][C:8]=3[Cl:10])[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]=2[CH:23]=1

Participants

4

Reactant 2

HCID 59436026HCID 59436026, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59435994HCID 59435994, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[(4-acetyl-2,6-dichlorophenyl)amino]-9-bromobenzo[c]-2,6-naphthyridin-1(2H)-one (Examples 94 and 95, Step 2) (109 mg, 0.23 mmol) in THF (3 mL) at −10° C. under nitrogen atmosphere was added methyl magnesium bromide (0.61 mL, 3.0 M in THF/toluene). The reaction mixture was stirred for 1 h keeping temperature between −5° C.-0° C. After allowing to warm to room temperature, the solution was quenched with water and diluted with 1:3 iPrOH/CHCl3 and neutralized with sat. NaHCO3. The organic layer was dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with methanol in dichloromethane to afford the title compound.

Workup

  1. custombetween −5° C.-0° C
  2. customthe solution was quenched with water
  3. additiondiluted with 1:3 iPrOH/CHCl3 and neutralized with sat. NaHCO3
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel eluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-2b144f6e7727413681d2c4ebacbfc5da
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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