Ethyl Beta-Carboline-3-Carboxylate → 3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

HRID 355817Notes

Reaction equation

HRID 355817 reaction equation
[O-]CC.[Na+].[Na].[CH:6]1([C:9](=[NH:11])[NH2:10])[CH2:8][CH2:7]1.C([O:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=3)=O)C>O.C(O)C.C1(C)C=CC=CC=1>[CH:6]1([C:9]2[N:10]=[C:15]([C:17]3[N:18]=[CH:19][C:20]4[NH:21][C:22]5[C:27]([C:28]=4[CH:29]=3)=[CH:26][CH:25]=[CH:24][CH:23]=5)[O:14][N:11]=2)[CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 431751CyclopropanecarboximidamideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 189407253-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineYield 52%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of sodium ethoxide, prepared from sodium metal (0.6 g, 26 mmol) and anhydrous ethanol (50 mL), cyclopropylmethanimidamide (1.67 g, 16 mmol) and 9H-β-carboline-3-carboxylic acid ethyl ester (2.0 g, 8.0 mmol) were added. Toluene (50 mL) was added and the resulting mixture was heated to 120°-130° C. The ethanol and water formed during the reaction were removed by azeotropic distillation. The reaction was complete after 30 min. The solid was filtered from the reaction mixture, washed with water and dried. This afforded the title compound (1.15 g, 52%) as an yellow solid. M.p. 256°-257° C.

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was heated to 120°-130° C
  3. customwere removed by azeotropic distillation
  4. filtrationThe solid was filtered from the reaction mixture
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-a5fa28fb02984bcaa1055039dc7cd15f
Source dataset
uspto-grants-1998_11
Patent number
US05834482

Reaction notes

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