Methylamine → 5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,4-dimethyl-pent-3-enamide

HRID 918760Notes

Reaction equation

HRID 918760 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[C:15](/[CH3:25])=[CH:16]\[C:17](=[N:22]/[O:23][CH3:24])\[C:18]([O:20]C)=O)=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][NH2:27]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:25])=[CH:16][C:17](=[N:22][O:23][CH3:24])[C:18]([NH:27][CH3:26])=[O:20])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89661753methyl (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-4-methylpent-3-enoate

Product 1

HCID 1234254855-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,4-dimethyl-pent-3-enamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.68 g (1.87 mmol) methyl(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-4-methyl-pent-3-enoate and E-isomer from the previous reaction have been dissolved in 3.0 ml THF. 2.0 ml 40% aqueous methylamine have been added at ambient temperature with stirring which was continued over night. After removal of the solvent in vacuo the mixture was purified by chromatography on silica with a heptane/ethyl acetate gradient. 90 mg of the desired Z-isomer have been collected. 1H-NMR (CDCl3): δ=2.03 (s); 2.85 (d); 3.97 (s); 4.64 (s); 5.87 (s); 6.02 (d); 6.65 (br); 7.35 (d); 7.50 (d); 7.67 (d).

Workup

  1. waitwas continued over night
  2. customAfter removal of the solvent in vacuo the mixture
  3. customwas purified by chromatography on silica with a heptane/ethyl acetate gradient
  4. custom90 mg of the desired Z-isomer have been collected

Sources & evidence

ORD record
ord-02445459c6a74033bffeb3cffd807533
Source dataset
uspto-grants-2016_03
Patent number
US09271501B2

Reaction notes

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