Dimethylamine → 8-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053035ノート

反応式

HRID 2053035 の反応式
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12]1[C:13]2[N:14]([C:21]([CH3:25])=[C:22]([CH3:24])[N:23]=2)[CH:15]=[C:16]([C:18]([OH:20])=O)[CH:17]=1.[CH3:26][NH:27][CH3:28]>ClCCl>[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12]1[C:13]2[N:14]([C:21]([CH3:25])=[C:22]([CH3:24])[N:23]=2)[CH:15]=[C:16]([C:18]([N:27]([CH3:28])[CH3:26])=[O:20])[CH:17]=1

参加物

4

反応物 2

HCID 674DimethylamineHCID 691143868-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid

生成物 1

HCID 691059728-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3.0 g (8.9 mmol)-8-(trans-2,3-dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid and 3.7 g (11.6 mmol) —O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) are suspended in 150 ml dichloromethane and 3.2 ml (17.8 mmol) dimethylamine (5.6 M in ethanol) are added to the reaction mixture. After stirring for 16 h at room temperature, the reaction mixture is extracted with saturated aqueous sodium hydrogencarbonate. The organic phase is separated, dried over anhydrous magnesium sulphate and evaporated. The residue is dissolved in 10 ml dichloromethane and 50 ml diethyl ether are added. After stirring for 30 min, the precipitate is collected, washed with diethyl ether and dried in vacuo to give 2.35 g (73%) of the title compound as a colourless solid (m.p. 148-149° C.).

後処理

  1. extractionthe reaction mixture is extracted with saturated aqueous sodium hydrogencarbonate
  2. customThe organic phase is separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated
  5. dissolutionThe residue is dissolved in 10 ml dichloromethane
  6. addition50 ml diethyl ether are added
  7. stirringAfter stirring for 30 min
  8. customthe precipitate is collected
  9. washwashed with diethyl ether
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-cdc1743f18414b10ba52779bf2d8db75
出典データセット
uspto-grants-2008_02
特許番号
US07326718B2

反応ノート

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