2-Amino-3-(2-methylbenzylamino)pyridine → 8-(2-Methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

HRID 4301

反応式

HRID 4301 の反応式
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:22]([CH2:26][C:27]#[CH:28])[C:23](=O)[CH3:24])(C)(=O)=O>C(O)C>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:7]1[C:2]2[N:3]([C:22]([CH2:26][C:27]#[CH:28])=[C:23]([CH3:24])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 138258912-Amino-3-(2-methylbenzylamino)pyridineHCID 143683463-Mesyloxy-5-hexyn-2-one

生成物 1

HCID 138259268-(2-Methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine収率 30.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-amino-3-(2-methylbenzylamino)pyridine (2 g) and 3-mesyloxy-5-hexyn-2-one (1.78 g) in ethanol (40 ml) was refluxed for 31.5 hours and then evaporated in vacuo. The residue was treated with aqueous sodium bicarbonate solution and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (40 g) with a mixtutre of methylene chloride and ethyl acetate (50:1 to 10:1) as an eluent to give 8-(2-methylbenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.82 g).

後処理

  1. customevaporated in vacuo
  2. additionThe residue was treated with aqueous sodium bicarbonate solution
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (40 g) with a mixtutre of methylene chloride and ethyl acetate (50:1 to 10:1) as an eluent

出典と根拠

ORDレコード
ord-02f0036534674dbdbf7bb937e43757ec
出典データセット
uspto-grants-1988_02
特許番号
US04725601

関連ノート

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