Hydrochloric Acid → 1-Cyclopropylmethyl-4-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazin-2-one

HRID 1581639Notes

Reaction equation

HRID 1581639 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.[CH:39]1([CH2:42][N:43]2[CH2:48][CH2:47][NH:46][CH2:45][C:44]2=[O:49])[CH2:41][CH2:40]1.Cl>CN(C)C=O.O>[CH:39]1([CH2:42][N:43]2[CH2:48][CH2:47][N:46]([C:14]3[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:11]4[N:10]=[N:9][C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])=[C:12]4[N:13]=3)[CH2:45][C:44]2=[O:49])[CH2:40][CH2:41]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 227220171-(Cyclopropylmethyl)piperazin-2-oneHCID 865873523-(2-Fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-a]quinazoline

Product 1

HCID 102019961-Cyclopropylmethyl-4-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazin-2-oneYield 21%

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 (0.10 g, 0.23 mmol), triethylamine (1 ml, 7.2 mmol) and 1-cyclopropylmethylpiperazin-2-one.HCl (0.22 g, 1.15 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 (15 ml) and extracted with EtOAc (2×75 ml). The combined organic extracts were washed with brine, dried over MgSO4 and evaporated to give a brown oil. Purification by preparative thin layer chromatography eluting with CH2Cl2:MeOH (93:7) gave 1-cyclopropylmethyl-4-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-α]quinazolin-5-yl]piperazin-2-one (0.020 g, 21%) as a white solid. δH (400 MHz; CDCl3) 0.26-0.31 (2H, m), 0.52-0.58 (2H, m), 0.99-1.05 (1H, m), 3.37 (2H, d, J=7), 3.77 (2H, dd, J=5 and 5), 3.97 (2H, dd, J=5 and 5), 4.39 (2H, s), 7.20-7.31 (2H, m), 7.35-7.41 (1H, m), 7.66 (1H, dd, J=7 and 7), 7.94 (1H, dd, J=8 and 8), 8.02-8.11 (2H, m), 8.72 (1H, d, J=8); m/z (ES+) 417 (M+H+).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (2×75 ml)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give a brown oil
  7. customPurification by preparative thin layer chromatography
  8. washeluting with CH2Cl2:MeOH (93:7)

Sources & evidence

ORD record
ord-ebba54701d5d49d7a394d9df2e5a8325
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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