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

HRID 2053036ノート

反応式

HRID 2053036 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.F[B-](F)(F)F.[N:31]1(OC(N(C)C)=[N+](C)C)[C:35]2C=CC=CC=2N=N1.CN.C(=O)([O-])O.[Na+]>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]([NH:31][CH3:35])=[O:20])[CH:17]=1

参加物

6

反応物 4

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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 691140388-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-6-(N-methylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine収率 20%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.0 g (3.0 mmol) 8-(trans-2,3-dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid and 1.2 g (3.9 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) are suspended in 50 ml dichloromethane and 0.74 ml (6.0 mmol) methylamine (8 M in ethanol) are added to the reaction mixture. After stirring for 3 d at room temperature, the reaction mixture is hydrolyzed with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The combined organic phases are dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (20:1) and crystallization from diethyl ether/light petroleum ether yields 0.2 g (20%) of the title compound as a colourless solid (m.p. 143-144° C.).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over anhydrous magnesium sulphate
  3. customevaporated
  4. customPurification of the residue by column chromatography on silica gel
  5. customdichloromethane:methanol (20:1) and crystallization from diethyl ether/light petroleum ether

出典と根拠

ORDレコード
ord-4fc2c84d0adf407f98bfa701c55e6b86
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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