1-Methylpiperazine → HCID 71281048, compound

HRID 1497894Notes

Reaction equation

HRID 1497894 reaction equation
O=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([O:15][CH2:16]C)=[O:14])=[CH:11][N:12]=2)[CH:9]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]3[N:8]([C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:12]=3)[CH:9]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86677457HCID 86677457, compound

Product 1

HCID 71281048HCID 71281048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of crude ethyl 6-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxylate (112) (214 mg, 0.92 mmol) in DCM (5 mL) and 1-methylpiperazine (231 L, 2.30 mmol) at room temperature was added portion-wise sodium triacetoxyborohydride (586 mg, 2.77 mmol). The reaction was stirred at room temperature overnight. The solvent was concentrated. The crude was taken in 10% sodium bicarbonate and ethyl acetate. The organic was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by silica chromatography to afford methyl 6-(2-(4-methylpiperazin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxylate (113). MS m/z 304.4 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. washThe organic was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-4c3b7fcc431b486da0e54f81c4b48261
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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