Triethylamine → 8-(trans-2,3-Dihydro-2-hydroxy-7-methoxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053044Notes

Reaction equation

HRID 2053044 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[CH:20]2[CH2:21][C:22]3[C:27]([CH:19]12)=[C:26]([O:28][CH3:29])[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](=[C:26]([O:28][CH3:29])[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 237308448-Hydroxy-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamideHCID 866048921,2-Epoxy-7-methoxy-indane

Product 1

HCID 691058528-(trans-2,3-Dihydro-2-hydroxy-7-methoxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridineYield 19.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.8 g (3.4 mmol) 6-(N,N-dimethylamino-carbonyl)-8-hydroxy-2,3-dimethyl-imidazo[1,2-a]pyridine in 16 ml ethanol and 4 ml water are added 1.0 g (6.2 mmol) 1,2-epoxy-7-methoxy-indane and 0.48 ml triethylamine. After 4 h at 30° C., the mixture is cooled down and partitioned between di-chloromethane and saturated aqueous ammonium chloride. 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:triethylamine (8:1:1) yields 0.26 g (19%) of the title compound as a colourless solid (m.p. 129° C.).

Workup

  1. temperaturethe mixture is cooled down
  2. custompartitioned between di-chloromethane and saturated aqueous ammonium chloride
  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

Sources & evidence

ORD record
ord-0ab497e3a38840eabe6700fbfb63f38b
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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