Triethylamine → HCID 22244700, compound

HRID 891154Notes

Reaction equation

HRID 891154 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[N:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=2)[N:3]=1.[CH2:22]([N:24](CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[K+]>ClCCl.C(OCC)(=O)C.C1(C)C=CC=CC=1.O.CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[N:19]=[CH:18][C:17]([CH2:20][C:22]#[N:24])=[CH:16][CH:15]=2)[N:3]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 31297Methanesulfonyl chlorideHCID 22244691HCID 22244691, compound

Product 1

HCID 22244700HCID 22244700, compoundYield 41%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of [6-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)pyridin-3-yl]methanol (step 2, 1.51 g, 5.41 mmol), triethylamine (0.90 mL, 6.49 mmol), and dichloromethane (30 mL) was added methanesulfonyl chloride (0.46 mL, 5.95 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 1 h. The mixture was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4, and concentrated under reduced pressure. The residue was treated with potassium cyanide (1.76 g, 27.0 mmol), N,N-dimethylformamide (25 mL) and water (5 mL) at 65° C. for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and toluene (2:1) and washed with water. The organic fraction was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with hexane/ethyl acetate (6:1) to afford 0.63 g (41%) of the title compound: MS (ESI) m/z 289 [M+H]+, 287 [M−H]−, 1H-NMR (CDCl3) δ 8.39-8.38 (1H, m), 7.94 (1H, d, J=8.6 Hz), 7.79-7.76 (1H, m), 7.46-7.29 (5H, m), 3.77 (2H, s), 2.61 (3H, s), 2.31 (3H, s).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. temperatureAfter cooling to room temperature
  5. washwashed with water
  6. dry with materialThe organic fraction was dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica-gel column chromatography
  9. washeluting with hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-c0d8e3f6e12743f48adf0204a7ec9968
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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