1,1'-Carbonyldiimidazole → HCID 9954629, compound

HRID 2166359Notes

Reaction equation

HRID 2166359 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:23][O:24][CH3:25])=[C:11]([C:20](O)=[O:21])[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:40](=[N:44]O)([NH2:43])[CH2:41][CH3:42]>CN(C)C=O>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:23][O:24][CH3:25])=[C:11]([C:20]4[O:21][N:44]=[C:40]([CH2:41][CH3:42])[N:43]=4)[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4092053N-Hydroxypropionimidamide2×HCID 13800024HCID 13800024, compound

Product 1

HCID 9954629HCID 9954629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.74 g of 5-(4-chlorophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid are dissolved in 150 ml of absolute dimethylformamide, mixed with 2.91 g of carbonyldiimidazole and stirred for 3 hours at room temperature. To this solution is added 3.96 g of propionamidoxime, it is stirred for 8 hours, 1 g of propionamidoxime is added once more and also stirred for 8 hours. After evaporation on the oil pump vacuum, it is taken up in toluene and refluxed for 8 hours. After evaporation, it is chromatographed twice over silica gel, first with methylene chloride/ethanol=10:1 and then with hexane: acetone=1:1 as eluant. After recrystallization from ethyl acetate/hexane and drying over phosphorus pentoxide at 80° C. in a vacuum, 2.2 g of 5-(4-chlorophenoxy-3-(3-ethyl-1,2,4-oxadizaol-5-yl)-4-methoxymethyl-beta-carboline with a melting point of 170° C. is obtained.

Workup

  1. stirringis stirred for 8 hours
  2. stirringalso stirred for 8 hours
  3. customAfter evaporation on the oil pump vacuum, it
  4. temperaturerefluxed for 8 hours
  5. customAfter evaporation, it
  6. customis chromatographed twice over silica gel, first with methylene chloride/ethanol=10:1
  7. customAfter recrystallization from ethyl acetate/hexane
  8. dry with materialdrying over phosphorus pentoxide at 80° C. in a vacuum, 2.2 g of 5-(4-chlorophenoxy-3-(3-ethyl-1,2,4-oxadizaol-5-yl)-4-methoxymethyl-beta-carboline with a melting point of 170° C.
  9. customis obtained

Sources & evidence

ORD record
ord-9d1983271afc47c7b5c9ffe1edccfa96
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

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