4-Methylmorpholine → 4-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide

HRID 403266Notes

Reaction equation

HRID 403266 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][N:5]([CH:7]([F:9])[F:8])[CH:6]=1.Cl.[CH3:14][NH:15][O:16][CH3:17].CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>ClCCl>[CH3:17][O:16][N:15]([CH3:14])[C:10]([C:3]1[C:2]([Cl:1])=[CH:6][N:5]([CH:7]([F:9])[F:8])[N:4]=1)=[O:12]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574758564-chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 580828434-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid (150 mg, 0.76 mmole) in dichloromethane (5 ml) was subsequently treated at 23° C. with N,O-dimethylhydroxylamine hydrochloride (78 mg, 0.80 mmole), N-methylmorpholine (0.09 ml, 0.8 mmole) and EDCI.HCl (154 mg, 0.8 mmole) and stirring was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H2O, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (2:1) to give the title compound (164 mg) as a colorless oil. MS: m/z=240.1 [M]+.

Workup

  1. washThe mixture was washed with 1 M aqueous HCl and H2O
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c4f9297f4f3045b0b2c2ed82ab177a6c
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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