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

HRID 2053035Notes

Reaction equation

HRID 2053035 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-cdc1743f18414b10ba52779bf2d8db75
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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