Potassium Carbonate → N-(3-Cyano-4-neopentyloxyphenyl)-5-methylpyrazole-4-carboxamide

HRID 1744576노트

반응식

HRID 1744576 반응식
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([OH:9])=O.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:19][CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:15]([CH:18]=1)[C:16]#[N:17].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]([C:15]1[CH:18]=[C:11]([NH:10][C:7]([C:3]2[CH:4]=[N:5][NH:6][C:2]=2[CH3:1])=[O:9])[CH:12]=[CH:13][C:14]=1[O:19][CH2:20][C:21]([CH3:23])([CH3:22])[CH3:24])#[N:17]

참가 물질

7

반응물 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5576005-methyl-1H-pyrazole-4-carboxylic acidHCID 178227345-Amino-2-neopentyloxybenzonitrile

생성물 1

HCID 22227878N-(3-Cyano-4-neopentyloxyphenyl)-5-methylpyrazole-4-carboxamide수율 16.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Methylpyrazole-4-carboxylic acid (2 g), 5-amino-2-neopentyloxybenzonitrile (3.2 g), 1-hydroxybenzotriazole (2.5 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (3.6 g) were added to dimethylformamide (110 ml) and the mixture was stirred at room temperature for 5 h. The reaction mixture was treated with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=100:1), and the obtained oily substance was recrystallized from a mixed solvent of toluene-n-hexane to give the title compound (0.8 g), melting point: 133–134° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=100:1)
  6. customthe obtained oily substance was recrystallized from a mixed solvent of toluene-n-hexane

출처 및 근거

ORD 기록
ord-5c5502e1e3d74bafba87b19509137c02
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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