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

HRID 570261ノート

反応式

HRID 570261 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d9a616051d5e4f0ebcf5ad6779b57b5f
出典データセット
uspto-grants-2015_05
特許番号
US09023846B2

反応ノート

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