Ethyl orthoformate → HCID 178480782、化合物

HRID 1045768ノート

反応式

HRID 1045768 の反応式
[Br:1][C:2]1[C:3]([NH2:16])=[C:4]([NH2:15])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH:17](OCC)(OCC)OCC>>[Br:1][C:2]1[C:3]2[NH:16][CH:17]=[N:15][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

参加物

3

反応物 2

HCID 31214Ethyl orthoformateHCID 584469905-Bromo-2-(4-methyl-1-piperazinyl)-3,4-pyridinediamine

生成物 1

HCID 178480782HCID 178480782、化合物収率 79%

反応条件

温度
130 °C

実験手順

A 100 mL round bottom flask was charged with 5-bromo-2-(4-methylpiperazin-1-yl)pyridine-3,4-diamine (1.1 g, 3.8 mmol) and triethyl orthoformate (20 mL). The resulting mixture was stirred at 130° C. for 1 h. Reaction progress was monitored by TLC (EtOAc/petroleum ether=2:1). Work-up: the reaction mixture was concentrated in vacuo. The residue was re-dissolved in EtOAc (50 mL) and washed with brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 10-40% EtOAc in CH2Cl2, to afford 0.9 g (79%) of the product as a white solid. MS m/z: 296 (M+H+).

後処理

  1. customReaction progress
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was re-dissolved in EtOAc (50 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with 10-40% EtOAc in CH2Cl2

出典と根拠

ORDレコード
ord-a1764a9570b245dfbb264b97a248384a
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

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