Potassium Carbonate → 6-Chloro-2-(4-methyl-piperazin-1-yl)-3-nitro-pyridin-4-ylamine

HRID 1481581Notes

Reaction equation

HRID 1481581 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([Cl:12])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>CN(C=O)C.O>[Cl:12][C:4]1[N:3]=[C:2]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 2827402,6-Dichloro-3-nitropyridin-4-amine

Product 1

HCID 866574286-Chloro-2-(4-methyl-piperazin-1-yl)-3-nitro-pyridin-4-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,6-dichloro-3-nitro-pyridin-4-ylamine (0.500 g, 2.40 mmol) in DMF (5 mL) was treated with K2CO3 (1.66 g, 12.0 mmol) and 1-methylpiperazine (0.267 mL, 2.40 mmol) at room temperature for 18 h. The resulting mixture was diluted with water (75 mL) and extracted three times with EtOAc (50 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 24-g SEPRA Si 50 SPE column (Isco system: Flow rate=15 mL/min; Eluent=EtOAc-hexanes, 3:1 v/v for 5 min, then 3:1 to 1:0 v/v over 40 min) to yield 6-chloro-2-(4-methyl-piperazin-1-yl)-3-nitro-pyridin-4-ylamine as a bright yellow solid. 1H-NMR (400 MHz, CD3OD) δ: 6.22 (s, 1H), 3.39-3.45 (m, 4H), 2.49-2.55 (m, 4H), 2.34 (s, 3H). Mass Spectrum (LCMS, APCI pos.): Calculated for C10H14ClN5O2: 272.1 (M+H). Measured: 272.1.

Workup

  1. extractionextracted three times with EtOAc (50 mL)
  2. dry with materialThe combined extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on a 24-g SEPRA Si 50 SPE column (Isco system

Sources & evidence

ORD record
ord-b72836350d2a47498d2028cd2b0f97c2
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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