HCID 13837186, compound → 3-(3-Ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

HRID 355814Notes

Reaction equation

HRID 355814 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14](N2C=CN=C2)=O)[N:2]=1.[OH:21][NH:22][C:23](=[NH:26])[CH2:24][CH3:25]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:24]([C:23]1[N:26]=[C:14]([C:3]2[N:2]=[CH:1][C:13]3[NH:12][C:11]4[C:6]([C:5]=3[CH:4]=2)=[CH:7][CH:8]=[CH:9][CH:10]=4)[O:21][N:22]=1)[CH3:25]

Participants

5

Reactant 2

HCID 13837186HCID 13837186, compoundHCID 178458070HCID 178458070, compound

Product 1

HCID 189407053-(3-Ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineYield 56.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound 1 (1.05 g, 4 mmol) in a mixture of toluene (50 mL) and DMF (50 mL), N-hydroxypropanimidamide (0.53 g, 6 mmol) was added. The resulting mixture was heated at 140°-150° C. for 7 h, and stirring continued for 3 days at room temperture. The solvents were removed in vacuo, and the oily residue precipitated from water. The white solid (1.0 g) was dried and submitted to column chromatography on silica gel with CH2Cl2 /methanol(9:1) as eluent. This afforded the title compound (0.6 g, 56%). M.p. 146°-149° C.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated at 140°-150° C. for 7 h
  3. customThe solvents were removed in vacuo
  4. customthe oily residue precipitated from water
  5. dry with materialThe white solid (1.0 g) was dried

Sources & evidence

ORD record
ord-b526b37c7ff642cfaae9c95924f7015f
Source dataset
uspto-grants-1998_11
Patent number
US05834482

Reaction notes

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