Piperazine → HCID 66953548, compound

HRID 1511784Notes

Reaction equation

HRID 1511784 reaction equation
Br[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)CCCC>[CH3:13][O:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:3]=[CH:4][N:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 534216178-Bromo-2-methoxy-1,5-naphthyridine

Product 1

HCID 66953548HCID 66953548, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A solution of 8-bromo-2-methoxy-[1,5]naphthyridine (4.78 g, 20 mmol, prepared as in WO 2006/032466) and piperazine (8.6 g, 100 mmol) in 1-pentanol (20 mL) was heated at 80° C. over night. The mixture was cooled and the precipitate filtered off. The filtrate was diluted with EA (100 mL) and washed with water (20 mL). The aq. phase contains some product, which was extracted with DCM/MeOH 9:1 (3×30 mL). The org. phases were combined, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by CC (EA/MeOH 4:1 to MeOH) to give the desired intermediate (4.7 g, 96%) as yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate filtered off
  3. additionThe filtrate was diluted with EA (100 mL)
  4. washwashed with water (20 mL)
  5. extractionwas extracted with DCM/MeOH 9:1 (3×30 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by CC (EA/MeOH 4:1 to MeOH)

Sources & evidence

ORD record
ord-de8af0105e6a443eaa43fb9f7b105f2d
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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