Dimethylamine, hydrochloride → N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

HRID 467633노트

반응식

HRID 467633 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.[CH3:13][N:14](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:15].[B-](F)(F)(F)F.Cl.CNC.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:13][N:14]([CH3:15])[C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]

참가 물질

6

반응물 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 67076071N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid (500 mg, 2.92 mmol) in DMF (5 ml) under inert gas atmosphere was treated with TBTU (1030 mg, 3.2 mmol), dimethylamine hydrochloride (262 mg, 3.2 mmol) and N,N-diisopropylethylamine (2.0 ml, 11.7 mmol) and stirring was continued for 4 h. All volatiles were removed and the crude product was extracted with water and ethyl acetate. The organic phase was washed with sodium bicarbonate and the aqueous phases were back-extracted with ethyl acetate and dichloromethane. The combined organic phases were dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a dichloromethane/methanol gradient as white solid (230 mg, 40%).

후처리

  1. customAll volatiles were removed
  2. extractionthe crude product was extracted with water and ethyl acetate
  3. washThe organic phase was washed with sodium bicarbonate
  4. extractionthe aqueous phases were back-extracted with ethyl acetate and dichloromethane
  5. customThe combined organic phases were dried
  6. customthe solvent was evaporated
  7. customThe product was obtained
  8. customafter purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-803839c5a5684682adf59b8aa530745e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623866B2

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