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

HRID 2053035노트

반응식

HRID 2053035 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-cdc1743f18414b10ba52779bf2d8db75
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326718B2

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