Dabco → HCID 123419027, compound

HRID 1807387Notes

Reaction equation

HRID 1807387 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:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C@@H:21]1[CH2:23][C@H:22]1[CH:24]([NH:26][O:27][CH3:28])[CH3:25].C1N2CCN(CC2)C1>C(#N)C>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C@@H:21]1[CH2:23][C@H:22]1[CH:24]([N:26]([O:27][CH3:28])[C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9])[CH3:25]

Participants

5

Reactant 3

HCID 9237DabcoHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 88851623HCID 88851623, compound

Product 1

HCID 123419027HCID 123419027, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (80 mg; 0.41 mmol) in acetonitrile (1 ml) was added dropwise to a stirred mixture of trans-N-{1-[2-(2,4-dichlorophenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine diastereomere B (88 mg; 0.34 mmol), prepared as described in example P13 and DABCO (54 mg; 0.48 mmol) in acetonitrile (1 ml) at ambient temperature. The reaction mixture was stirred for 16 hours at ambient temperature. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (10 g) (eluent: n-hexane/ethyl acetate 1:1).

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography over silica gel (10 g) (eluent: n-hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-1844a6185343419d9ba67cf3db2a3927
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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