Picolyl chloride → HCID 59511226, compound

HRID 1157318Notes

Reaction equation

HRID 1157318 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:13]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:12][NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1>CN(C=O)C>[C:3]1([C:9]2[C:13]([N:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)=[CH:12][N:11]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[N:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 178452251HCID 178452251, compound

Product 1

HCID 59511226HCID 59511226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To sodium hydride (0.1 g) taken in a dry 100 ml 3-necked round bottom flask cooled to 0° C. dry DMF (2 ml) was added under nitrogen. To the above mixture compound tert-butyl 4-(3-phenyl-1H-pyrazol-4-yl)piperazine-1-carboxylate (0.5 g) in DMF (2 ml) was slowly added and allowed to stir at 0° C. for 30 minutes. 2-Chloromethyl pyridine (300 mg) in DMF (1 ml) was slowly added to the above mixture at 0°C. The reaction mixture was allowed to stir at room temperature for overnight and quenched with ice. The product was extracted with ethyl acetate (3×10 ml). The combined organic layer was washed with water, brine, dried over sodiumsulphate and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 6% ethyl acetate in hexane, to afford tert-butyl 4-(3-phenyl-1-(pyridin-2-ylmethyl)-1H-pyrazol-4-yl)piperazine-1-carboxylate as half white solid.

Workup

  1. additionwas added under nitrogen
  2. stirringto stir at room temperature for overnight
  3. customquenched with ice
  4. extractionThe product was extracted with ethyl acetate (3×10 ml)
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over sodiumsulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-86f0204bf34c4798866068e50f00850a
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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