Pyridine → HCID 19799516, compound

HRID 2081284Notes

Reaction equation

HRID 2081284 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25](Cl)=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:28]([NH2:31])([CH3:30])[CH3:29].N1C=CC=CC=1>ClCCl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([NH:31][CH:28]([CH3:30])[CH3:29])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6363IsopropylamineHCID 19799508HCID 19799508, compound

Product 1

HCID 19799516HCID 19799516, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]pyrazole-3-carbonyl chloride (550 mg) in dichloromethane (5 ml) were added isopropylamine (0.2 ml) and pyridine (0.2 ml), and the mixture was stirred at room temperature for 0.5 hours. The mixture was then evaporated to dryness under reduced pressure, and the residue was shaken with a mixture of 0.1 N hydrochloric acid (50 ml), dichloromethane (15 ml), and ether (60 ml). The mixture was allowed to separate into layers. The organic layer was washed with an aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate, followed by evaporation of the solvent to give a light yellow syrup (550 mg, 98%).

Workup

  1. customThe mixture was then evaporated to dryness under reduced pressure
  2. stirringthe residue was shaken with a mixture of 0.1 N hydrochloric acid (50 ml), dichloromethane (15 ml), and ether (60 ml)
  3. customto separate into layers
  4. washThe organic layer was washed with an aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-84fb0fb8a16c4aef840e870d4257e087
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

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