(2-{[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester → {3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-propyl]-imidazo[1,5-a]pyridin-8-yloxy}-acetic acid ethyl ester

HRID 852229ノート

反応式

HRID 852229 の反応式
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[C:8]([CH2:13][NH:14][C:15](=O)[CH2:16][C:17]([N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])([CH3:19])[CH3:18])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[C:8]2[N:9]([C:15]([CH2:16][C:17]([N:20]3[C:28](=[O:29])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]3=[O:30])([CH3:19])[CH3:18])=[N:14][CH:13]=2)[CH:10]=[CH:11][CH:12]=1)[CH3:2]

参加物

3

反応物 1

HCID 69158493(2-{[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester

生成物 1

HCID 69157841{3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-propyl]-imidazo[1,5-a]pyridin-8-yloxy}-acetic acid ethyl ester収率 55.3%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

A solution of (2-{[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester (2.79 g, 6.349 mmol) in 100 ml of neat phosphoryl chloride is stirred at 75° C. for 16 hours. The reaction mixture is poured on 200 g of crushed ice and extracted with methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 96:4) to give 1.48 g of {3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-propyl]-imidazo[1,5-a]pyridin-8-yloxy}-acetic acid ethyl ester (55%).

後処理

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 96:4)

出典と根拠

ORDレコード
ord-f9ba79097cce49c8980951589ed751da
出典データセット
uspto-grants-2007_08
特許番号
US07253181B2

反応ノート

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