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

HRID 2053036노트

반응식

HRID 2053036 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.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

참가 물질

6

반응물 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

생성물 1

HCID 691140388-(trans-2,3-Dihydro-2-hydroxy-1-indenylamino)-6-(N-methylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine수율 20%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-4fc2c84d0adf407f98bfa701c55e6b86
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326718B2

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