Methanesulfonyl chloride → HCID 15428664, compound

HRID 1249690Notes

Reaction equation

HRID 1249690 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[N:10][N:11]([CH2:13][CH2:14]O)[CH:12]=2)=[CH:4][CH:3]=1.FC1C=CC(C2C=N[N:32]([CH2:40]CO)[C:33]=2C2C=CN=CC=2)=CC=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[N:10][N:11]([CH2:13][CH2:14][N:32]([CH3:40])[CH3:33])[CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 15428662HCID 15428662, compoundHCID 15908491HCID 15908491, compound

Product 1

HCID 15428664HCID 15428664, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-fluorophenyl)-3-(4-pyridinyl)-1H-pyrazole-1-ethanol (or 4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-pyrazole-1-ethanol) prepared as set forth in Example 11 (1.36 g) was dissolved in 30 mL pyridine and cooled to 0° C., whereupon methanesulfonyl chloride (0.6 mL) was added. After stirring at 0° C. for 12 hours, about 20 g of ice was added, and the mixture was extracted with toluene (300 ml). After evaporation, the residue was used directly without further purification. 0.7 g of the above obtained compound was dissolved in methanol (25 mL), and dimethylamine/THF solution (4M, 2 mL) was added. The reaction mixture was refluxed for 12 hours, then evaporates go dryness. The residue was purified by chromatography (methanol/dichloromethane 1:10). A mixture (0.59 g) of 4-(4-fluorophenyl)-N,N-dimethyl-3-(4-pyridinyl)-1H-pyrazole-1-ethanamine and 4-[(4-fluorophenyl)-N,N-dimethyl-5-(4-pyridinyl)-1H-pyrazole-1-ethanamine were obtained. 1H NMR: consistent with the assigned strucure. Mass spectrum, m/z: 311 (M+1). Anal. calc'd C18H19N4F.0.55 H2O: C, 67.50; H, 6.33; N, 17.49. Found: C, 67.21; H, 6.46; N, 17.14.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with toluene (300 ml)
  3. customAfter evaporation
  4. customthe residue was used directly without further purification
  5. dissolution0.7 g of the above obtained compound was dissolved in methanol (25 mL)
  6. additiondimethylamine/THF solution (4M, 2 mL) was added
  7. temperatureThe reaction mixture was refluxed for 12 hours
  8. customevaporates
  9. customThe residue was purified by chromatography (methanol/dichloromethane 1:10)

Sources & evidence

ORD record
ord-2be86a792d3f429c9e5557d682ac25b9
Source dataset
uspto-grants-2002_01
Patent number
US06335336B1

Reaction notes

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