Triethylamine → HCID 44595678, compound

HRID 467971Notes

Reaction equation

HRID 467971 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[Cl:13][C:14]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:15]=1[CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][NH:18]1.C(N(CC)CC)C>ClCCl>[Cl:13][C:14]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:15]=1[CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4690000HCID 4690000, compoundHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride

Product 1

HCID 44595678HCID 44595678, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At a temperature of 0° C., a solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.97 g; 5.0 mmol) in dichloromethane (5 ml) was added dropwise to a stirred suspension of 2-(2,6-dichloro-benzyl)-pyrrolidine (1.20 g; 5.0 mmol), which was prepared as described in example P17, and triethylamine (1.5 g; 15.0 mmol) in dichloromethane (15 ml). The ice bath was removed and reaction mixture was allowed stirring for 15 hours. The reaction mixture was washed with 2M NaOH (20 ml), 2M HCl (20 ml) and saturated NaCl (20 ml) and then dried over Na2SO4. After removal of the solvent, the residue (1.9 g oil) was purified by flash chromatography over silica gel (eluent:cyclohexane/ethyl acetate 3:7). 1.53 g (78.8% of theory) of [2-(2,6-dichloro-benzyl)-pyrrolidin-1-yl]-(3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-methanone was obtained in form of an oil.

Workup

  1. customwas prepared
  2. customThe ice bath was removed
  3. customreaction mixture
  4. washThe reaction mixture was washed with 2M NaOH (20 ml), 2M HCl (20 ml) and saturated NaCl (20 ml)
  5. dry with materialdried over Na2SO4
  6. customAfter removal of the solvent
  7. customthe residue (1.9 g oil) was purified by flash chromatography over silica gel (eluent:cyclohexane/ethyl acetate 3:7)

Sources & evidence

ORD record
ord-da9bc896da384ca083bc7ac46410d1a4
Source dataset
uspto-grants-2014_01
Patent number
US08623902B2

Reaction notes

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