Triethylamine → 3-(2-Fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline

HRID 1581631Notes

Reaction equation

HRID 1581631 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:13][C:12]=12.O.[NH:33]1[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]1.C(N(CC)CC)C>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([N:33]3[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]3)=[N:13][C:12]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21584170Piperidin-4-one hydrateHCID 865873523-(2-Fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-a]quinazoline

Product 1

HCID 99251083-(2-Fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazolineYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-α]quinazoline (Example 1, step b) (3.0 g, 6.91 mmol), 4-piperidone monohydrate, hydrochloride salt (1.28 g, 8.3 mmol) and triethylamine (3.0 ml, 21 mmol) in dry N,N-dimethylformamide (25 ml) was stirred at 60° C. under nitrogen for 4 h. The mixture was diluted with water (100 ml) and extracted with 10% methanol:dichloromethane (150 ml). The extract was dried (Na2SO4), filtered and concentrated. The residual solid was washed with diethyl ether-ethyl acetate and dried in vacuo to give 3-(2-fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline (1.90 g, 76%). δH (360 MHz; DMSO) 2.67 (4H, t, J=6), 3.99 (4H, t, J=6), 7.33-7.48 (3H, m), 7.78 (1H, dd, J=7 and 7), 8.05-8.11 (2H, m), 8.25 (1H, d, J=8), 8.58 (1H, d, J=8); m/z (ES+) 362 (M+H+).

Workup

  1. extractionextracted with 10% methanol
  2. dry with materialThe extract was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe residual solid was washed with diethyl ether-ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-13742962c291493d8e62f51b9200c8ae
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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