Methylamine → HCID 22267915, compound

HRID 2298027Notes

Reaction equation

HRID 2298027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][C:3]=1[N:11]1[C:15]([CH:16]2[CH2:18][CH2:17]2)=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[N:12]1.[CH3:24][NH2:25]>S(Cl)(Cl)=O.C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:25][CH3:24])=[O:10])=[CH:4][C:3]=1[N:11]1[C:15]([CH:16]2[CH2:17][CH2:18]2)=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[N:12]1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 22267774HCID 22267774, compound

Product 1

HCID 22267915HCID 22267915, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of ethyl 1-(2-chloro-5-hydroxycarbonylphenyl)-5-cyclopropyl-1H-pyrazole-4-carboxylate (1.32 g, 3.73 mmol) in thionyl chloride (7.5 mL) was heated at reflux for 2 h under a nitrogen atmosphere. The resulting solution was concentrated in vacuo. A solution of the residue in anhydrous CH2Cl2 (10 mL) under a nitrogen atmosphere was treated with methylamine (2 M solution in THF, 9.33 mL, 18.7 mmol) followed by a catalytic amount of 4-dimethylaminopyridine. The resulting mixture was stirred for 6 h and partitioned between ethyl acetate and HCl (1 M aq). The organic layer was washed with brine, NaHCO3 (sat aq sol), and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash 40M™ chromatography (75:25 ethyl acetate/hexanes) to afford 1.00 g (77% yield) of the title compound.

Workup

  1. temperatureat reflux for 2 h under a nitrogen atmosphere
  2. concentrationThe resulting solution was concentrated in vacuo
  3. custompartitioned between ethyl acetate and HCl (1 M aq)
  4. washThe organic layer was washed with brine, NaHCO3 (sat aq sol), and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash 40M™ chromatography (75:25 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a187dfcfb6bd4d70b34205bee411f74b
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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