Methylamine → HCID 86720958, compound

HRID 524902Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1.[CH3:18][NH2:19].C1COCC1>>[CH3:18][NH:19][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 86720948HCID 86720948, compound

Product 1

HCID 86720958HCID 86720958, compoundYield 93%

Procedure

1-(2-chloro-5-nitro-4-pyridyl)-4-methyl-piperazine (265.9 mg, 1.036 mmol) and methylamine 2M in THF (2.590 mL of 2 M, 5.180 mmol) were heated overnight in a sealed tube at 60° C. The mixture was purified by chromatography on silica (Companion 12 g) eluting with 0.5-15% MeOH:DCM, yielding N-methyl-4-(4-methylpiperazin-1-yl)-5-nitro-pyridin-2-amine (243 mg, 93%). MS (ES+) 252.1.

Workup

customThe mixture was purified by chromatography on silica (Companion 12 g)
washeluting with 0.5-15% MeOH

Sources & evidence

ORD record: ord-4259a3c752fb4ae1b9b22db110cc3100
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340546B2

Reaction notes

Loading…