5-chloro-N-methoxy-8-[4-(2-methoxyethyl)piperazin-1-yl]-N-methylquinoline-7-carboxamide → 1-{5-Chloro-8-[4-(2-methoxyethyl)piperazin-1-yl]quinolin-7-yl}ethanone

HRID 1192494Notes

Reaction equation

HRID 1192494 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](N(OC)C)=[O:13])[C:9]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][O:26][CH3:27])[CH2:20][CH2:19]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:28][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:13])[CH3:28])[C:9]([N:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][O:26][CH3:27])[CH2:22][CH2:23]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 866561755-chloro-N-methoxy-8-[4-(2-methoxyethyl)piperazin-1-yl]-N-methylquinoline-7-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 673016751-{5-Chloro-8-[4-(2-methoxyethyl)piperazin-1-yl]quinolin-7-yl}ethanoneYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 5-chloro-N-methoxy-8-[4-(2-methoxyethyl)piperazin-1-yl]-N-methylquinoline-7-carboxamide (63 mg, 0.16 mmol) in tetrahydrofuran (0.2 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (0.69 mL, 0.96 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 10% MeOH in dichloromethane, to give the desired product (22 mg, 39%). LCMS calculated for C18H23ClN3O2(M+H)+: m/z=348.1; found: 348.1.

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resultant residue was purified on silica gel
  7. washeluting with 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-1b564da12add41de9a155ce62f300d1f
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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