HCID 178446149, compound → 3-[2-(3-benzyl-1,2,4-oxadiazol-5-yl)ethyl]-9-pentyl-7-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 1664561Notes

Reaction equation

HRID 1664561 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([NH:17]/[N:18]=[C:19]2\[NH:20][C:21](=[O:37])[C:22]3[NH:23][C:24]([C:33]([F:36])([F:35])[F:34])=[N:25][C:26]=3[N:27]\2[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=O)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]2[N:20]3[C:21](=[O:37])[C:22]4[NH:23][C:24]([C:33]([F:35])([F:36])[F:34])=[N:25][C:26]=4[N:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:19]3=[N:18][N:17]=2)[O:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178446149HCID 178446149, compound

Product 1

HCID 576002473-[2-(3-benzyl-1,2,4-oxadiazol-5-yl)ethyl]-9-pentyl-7-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 17.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 3-(3-benzyl-1,2,4-oxadiazol-5-yl)-N′-[(2E)-6-oxo-3-pentyl-8-(trifluoromethyl)-1,3,6,7-tetrahydro-2H-purin-2-ylidene]propanohydrazide (220.1 mg, 0.424 mmole) in toluene (20 ml) was refluxed for 5 hours. After evaporation of solvent, the residue was purified by preparative LCMS to yield the desired product (37.9 mg, 17.8%) as white solid. LCMS calculated for C23H24F3N8O2 (M+H): 501.2. found 501.1.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter evaporation of solvent
  3. customthe residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-bc13da999dc04023957eac1619b50b2b
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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