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

HRID 1581629Notes

Reaction equation

HRID 1581629 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.C(N(CC)CC)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.ClCCl>CN(C)C=O.O.CO>[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:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[N:13][C:12]=12

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 865873523-(2-Fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-a]quinazoline

Product 1

HCID 98197453-(2-Fluorophenyl)-5-(morpholin-4-yl)-[1,2,3]triazolo[1,5-a]quinazolineYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-α]quinazoline (0.10 g, 0.23 mmol), triethylamine (0.10 ml, 0.7 mmol) and morpholine (0.025 g, 0.25 mmol) in dry N,N-dimethylformamide (2 ml) was stirred at 50° C. under nitrogen for 18 h. The mixture was cooled, then diluted with water (10 ml) and 10% methanol:dichloromethane (5 ml). The two phases were separated by filtration through a PTFE membrane and the organic layer was concentrated. Trituration and washing with ethyl acetate-diethyl ether gave 3-(2-fluorophenyl)-5-(morpholin-4-yl)-[1,2,3]triazolo[1,5-α]quinazoline (0.065 g, 81%). δH (360 MHz; DMSO) 3.61 (4H, dd, J=5 and 5), 3.86 (4H, dd, J=5 and 5), 7.34-7.39 (2H, m), 7.42-7.50 (1H, m), 7.77 (1H, dd, J=7 and 7), 8.04-8.10 (2H, m), 8.22 (1H, d, J=8), 8.59 (1H, d, J=8); m/z (ES+) 350 (M+H+).

Workup

  1. temperatureThe mixture was cooled
  2. customThe two phases were separated by filtration through a PTFE membrane
  3. concentrationthe organic layer was concentrated
  4. washTrituration and washing with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-ce95fec58e8f4b2096f91f956bb2af64
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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