1-Methylpiperazine → HCID 86720950, compound

HRID 524894Notes

Reaction equation

HRID 524894 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11]([NH2:18])[CH:10]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11]([NH2:18])[CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 51506864-chloro-5-nitropyridin-2-amine

Product 1

HCID 86720950HCID 86720950, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-methylpiperazine (265.5 mg, 294.0 mL, 2.651 mmol) in THF (5 mL) was added to a stirred suspension of 4-chloro-5-nitro-pyridin-2-amine (400 mg, 2.305 mmol) and DIPEA (357.5 mg, 481.8 mL, 2.766 mmol) in THF (10 mL) at 0° C. under an atmosphere of nitrogen. The reaction was allowed to stir at ambient temperature for 90 hours before the solvent removed in vacuo. The residue was tritruated from DCM/MeOH and the resultant precipitate was washed with DCM/MeOH solutions. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% 2M NH3 in MeOH/DCM) to give 4-(4-methylpiperazin-1-yl)-5-nitro-pyridin-2-amine as a yellow solid (355 mg, 65% Yield). MS (ES+) 238.1.

Workup

  1. customremoved in vacuo
  2. washthe resultant precipitate was washed with DCM/MeOH solutions
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% 2M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-921592f4a0e148aca42f7902fde02fc9
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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