Tetrahydrofuran → 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide

HRID 1773784Notes

Reaction equation

HRID 1773784 reaction equation
C([Mg]Cl)(C)C.C1COCC1.C(O[C:14]([C:16]1[N:17]([S:29](=[O:34])(=[O:33])[N:30]([CH3:32])[CH3:31])[N:18]=[C:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=1)=[O:15])C.Cl.[CH3:36][NH:37][O:38][CH3:39]>C(Cl)Cl.[NH4+].[Cl-]>[CH3:39][O:38][N:37]([CH3:36])[C:14]([C:16]1[N:17]([S:29](=[O:33])(=[O:34])[N:30]([CH3:31])[CH3:32])[N:18]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=1)=[O:15]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 67958277HCID 67958277, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 866738982-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amideYield 44%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A 2M solution of isopropylmagnesium chloride in THF (1.9 mL, 3.8 mmol) was added to a stirred suspension of 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.45 g, 1.27 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.16 g, 1.65 mmol) in DCM (6.5 mL) under nitrogen at −78° C. The mixture was slowly allowed to warm to room temperature and stirred for 16 hours. The mixture was diluted with a saturated solution of NH4Cl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide (0.2 g, 44% yield) as a colourless oil that solidified upon standing.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents were evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-9bff45c4aee146bb808263d83c064477
Source dataset
uspto-grants-2016_02
Patent number
US09255103B2

Reaction notes

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