Triethylamine → 4-[3-(2-Fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1581634Notes

Reaction equation

HRID 1581634 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.[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]>CN(C)C=O.O>[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:11]3[N:10]=[N:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[C:12]3[N:13]=2)[CH2:48][CH2:47]1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 865873523-(2-Fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-a]quinazoline

Product 1

HCID 700311884-[3-(2-Fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazine-1-carboxylic acid tert-butyl esterYield 88%

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 (0.33 g, 0.71 mmol), triethylamine (0.3 ml, 2.1 mmol) and piperazine-1-carboxylic acid tert-butyl ester (0.26 g, 1.4 mmol) in dry N,N-dimethylformamide (6 ml) was stirred at 50° C. under nitrogen for 18 h. The mixture was cooled, then diluted with water (30 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 flash column chromatography eluting with CH2Cl2:MeOH (93:7) gave 4-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-α]quinazolin-5-yl]piperazine-1-carboxylic acid tert-butyl ester as a white solid (0.28 g, 88%). δH (400 MHz; CDCl3) 1.50 (9H, s), 3.59-3.62 (4H, m), 3.69-3.72 (4H, m), 7.19-7.30 (2H, m), 7.32-7.37 (1H, m), 7.63 (1H, ddd, J=8, 8 and 1), 7.91 (1H, ddd, J=8, 8 and 1), 8.02 (1H, d, J=8), 8.11 (1H, ddd, J=7, 7 and 2), 8.70 (1H, dd, J=8 and 1).

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 flash column chromatography
  8. washeluting with CH2Cl2:MeOH (93:7)

Sources & evidence

ORD record
ord-48358e03041d4460a0ced08b9e3ed090
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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