Pyridine → HCID 57464483, compound

HRID 1821704Notes

Reaction equation

HRID 1821704 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[C:4]([OH:19])[CH:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Cl)(Cl)=[O:27].C1(C)C=CC=CC=1.N1CCCC1>O.C1(C)C=CC=CC=1>[N:20]1([C:21]([O:19][C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=2[O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 31268PyrrolidineHCID 19083224Phosgen tolueneHCID 178424441HCID 178424441, compound

Product 1

HCID 57464483HCID 57464483, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

200 mg (0.722 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was mixed with toluene (3 mL) and the mixture was ice-cooled. To the mixture were added 60 L (0.742 mmol) of pyridine, then 0.67 mL (0.724 mmol) of 1.08 mol/L phosgene-toluene solution under nitrogen atmosphere with stirring, and the resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was ice-cooled, 60 L (0.722 mmol) of pyridine, then 60 L (0.719 mmol) of pyrrolidine were added to the mixture, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 4 plates were used, developed by hexane:ethyl acetate=2:1) to obtain 190 mg (0.508 mmol, Yield: 70.7%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 1-pyrrolidinecarboxylate (Compound No. 1937).

Workup

  1. temperaturecooled
  2. temperaturecooled
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 4 plates were used, developed by hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-61aa36ca8dee46b39de5fd3e4ff038a2
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

Loading…