Benzylamine → N-benzyl-6-(4-methylpiperazin-1-yl)-3-nitropyridin-2-amine

HRID 930548Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.CCN(C(C)C)C(C)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>CN1C(=O)CCC1>[CH2:21]([NH:28][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)[N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,6-Dichloro-3-nitropyridine E-3.1″(1.5 g; 7.151 mmol) is suspended in NMP and cooled to 0° C. DIPEA (2.31 ml, 14.3 mmol) and benzylamine (800 μl; 7.47 mmol) are added, the reaction mixture is stirred at RT. To this suspension 1-methylpiperazine (875 μl; 7.87 mmol) is added and the resulting mixture is stirred for 16 h at 50° C. The crude intermediate is purified using reversed phase chromatography (prep. HPLC1). The product containing fractions are combined and freeze-dried (Yield: 49%; 1.144 g; 3.494 mmol)

Workup

stirringthe resulting mixture is stirred for 16 h at 50° C
customThe crude intermediate is purified
additionThe product containing fractions
customfreeze-dried (Yield: 49%; 1.144 g; 3.494 mmol)

Sources & evidence

ORD record: ord-00965cc0b5f1471e9eaffa1c7f99cce4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296748B2

Reaction notes

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