Triethylamine → 8-[(1S,2S)-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053042Notes

Reaction equation

HRID 2053042 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]([OH:16])[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=1)=[O:4].[O:18]1[C@H:20]2[CH2:21][C:22]3[C:27]([C@@H:19]12)=[CH:26][CH:25]=[CH:24][CH:23]=3.C(N(CC)CC)C>C(O)C.O>[OH:18][C@H:20]1[CH2:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:19]1[O:16][C:7]1[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=[C:5]([C:3]([N:2]([CH3:1])[CH3:17])=[O:4])[CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1512568(1R,2S)-epoxyindaneHCID 237308448-Hydroxy-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide

Product 1

HCID 104065358-[(1S,2S)-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridineYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.5 g (6.4 mmol) 6-(N,N-dimethylamino-carbonyl)-8-hydroxy-2,3-dimethyl-imidazo[1,2-a]pyridine in 30 ml ethanol and 7.5 ml water are added 1.7 g (12.9 mmol) (1R,2S)-epoxyindane and 1.8 ml triethylamine. After 3 h at 70° C., the mixture is cooled down and partitioned between dichloro-methane and water. The organic layer is separated, dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using ethyl acetate:light petroleum ether (1:1) and crystallization from diisopropyl ether yields 1.7 g (74%) of the title compound as a colourless solid (m.p. 122° C.).

Workup

  1. temperaturethe mixture is cooled down
  2. custompartitioned between dichloro-methane and water
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customPurification of the residue by column chromatography on silica gel
  7. customethyl acetate:light petroleum ether (1:1) and crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-ec1612091324462c8531edd9198f1432
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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