Methyl iodide → HCID 10134193, compound

HRID 1581637Notes

Reaction equation

HRID 1581637 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[N:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]3)=[N:15][C:14]=12.[CH3:30]I>CN(C)C(=O)C.O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[N:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([N:23]3[CH2:24][CH2:25][CH:26]([O:29][CH3:30])[CH2:27][CH2:28]3)=[N:15][C:14]=12

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 102700673-(2-Fluorophenyl)-5-(4-hydroxypiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline

Product 1

HCID 10134193HCID 10134193, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (60% dispersion in oil) (0.044 g, 1.10 mmol) was added to a solution of 3-(2-fluorophenyl)-5-(4-hydroxypiperidin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline (Example 9) (10 g, 0.27 mmol) in N,N-dimethylacetamide (4 ml). The mixture was stirred for 30 min before addition of methyl iodide (0.17 ml, 2.8 mmol) and then stirred for a further 18 h. The mixture was diluted with water (20 ml) and extracted with CH2Cl2 (2×50 ml). The combined organic extracts were washed with brine (20 ml), dried over MgSO4 and evaporated to give a colourless oil. Purification by preparative thin layer chromatography eluting with CH2Cl2:MeOH:NH3(c) (95:5:0.5) gave 3-(2-fluorophenyl)-5-(4-methoxypiperidin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline (0.067 g, 65%) as a yellow solid. δH (360 MHz; CDCl3) 1.84-1.90 (2H, m), 2.11-2.16 (2H, m), 3.36-3.41 (2H, m), 3.42 (3H, s), 3.51-3.54 (1H, m), 3.88-3.95 (2H, m), 7.19-7.29 (2H, m), 7.32-7.37 (1H, m), 7.60 (1H, ddd, J=8, 8 and 1), 7.88 (1H, ddd, J=8, 8 and 1), 8.01 (1H, d, J=8), 8.15 (1H, ddd, J=7, 7 and 2), 8.67 (1H, dd, J=8 and 1); m/z (ES+) 378 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (2×50 ml)
  2. washThe combined organic extracts were washed with brine (20 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto give a colourless oil
  6. customPurification by preparative thin layer chromatography
  7. washeluting with CH2Cl2:MeOH:NH3(c) (95:5:0.5)

Sources & evidence

ORD record
ord-3450074218f74b118115e160a6d6a66c
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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