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

HRID 2053036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053036
[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

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4fc2c84d0adf407f98bfa701c55e6b86
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326718B2

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