Water → Methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydroimidazo[4,5-a]quinolizine-10-carboxylate

HRID 362563Notes

Reaction equation

HRID 362563 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][NH:7][C:6](=S)[C:5]=2[N:4]=[CH:3]1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22](C2OC2(C#N)C#N)[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:33]([O:37][CH3:38])(=[O:36])[C:34]#[CH:35].[OH2:39].CN1[CH2:45][CH2:44]N(C)C1=O>>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:44]2[C:6](=[O:39])[N:7]3[C:35](=[C:34]([C:33]([O:37][CH3:38])=[O:36])[CH:45]=2)[C:5]2[N:4]=[CH:3][N:2]([CH3:1])[C:10]=2[CH:9]=[CH:8]3)=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 5

HCID 962WaterHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 13536Methyl propiolateHCID 193535981-Methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thioneHCID 193536803-(3-Benzyloxyphenyl)-oxirane-2,2-dicarbonitrile

Product 1

HCID 19353647Methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydroimidazo[4,5-a]quinolizine-10-carboxylateYield 34%

Procedure

3.50 g (21.2 mmol) of 1-methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione were dissolved in 0.6 l of 1,3-dimethyl-2-imidazolidinone at 140° C., left to cool to room temperature, treated with 5.9 g (21.4 mmol) of 3-(3-benzyloxyphenyl)-oxirane-2,2-dicarbonitrile and stirred over the weekend. Then, 7.8 ml of methyl propiolate were added and the mixture was stirred at 110° C. for 22 hours. After cooling the solution was stirred into 6 l of water, the precipitate was filtered off and it was chromatographed over silica gel with dichloromethane/acetone/hexane 2:1:1. There were obtained 3.20 g (34%) of methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydroimidazo[4,5-a]quinolizine-10-carboxylate as yellow crystals with m.p 196°-198° C.

Workup

  1. waitleft
  2. stirringthe mixture was stirred at 110° C. for 22 hours
  3. temperatureAfter cooling the solution
  4. filtrationthe precipitate was filtered off
  5. customit was chromatographed over silica gel with dichloromethane/acetone/hexane 2:1:1

Sources & evidence

ORD record
ord-5cd88568c614414c8e9452634fe7bdc5
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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