Water → HCID 58424873, compound

HRID 2409458Notes

Reaction equation

HRID 2409458 reaction equation
Cl.Cl.[CH3:3][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([O:22]C)[C:10]2[C:19]3[NH:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13](=[O:20])[NH:12][C:11]=2[CH:21]=1)[CH3:5].B(Br)(Br)Br.O>ClCCl>[CH3:5][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([OH:22])[C:10]2[C:19]3[NH:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13](=[O:20])[NH:12][C:11]=2[CH:21]=1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67381365HCID 67381365, compound

Product 1

HCID 58424873HCID 58424873, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-[(Dimethylamino)methyl]-10-methoxy-6-(methoxymethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5-(6H)-one (28 mg, 0.084 mmol) prepared in Example 72 was dissolved in dichloromethane (10 ml), added dropwise with boron tribromide (0.6 mmol, 152 mg) at 0° C. The mixture was stirred at room temperature for 2 hours and then water was added carefully. The solution was washed with chloroform, the water layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography (chloroform:ethanol=1:5) to obtain the title compound (14 mg, yield: 58%, white solid).

Workup

  1. washThe solution was washed with chloroform
  2. concentrationthe water layer was concentrated under reduced pressure
  3. customthe residue was purified by flash column chromatography (chloroform:ethanol=1:5)

Sources & evidence

ORD record
ord-9671e634056b40bc8af8cb3470e19e39
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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