Triethylamine → N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)-5-methylpyrazole-3-carboxamide

HRID 1744570노트

반응식

HRID 1744570 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([OH:16])=O)=[N:9]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:22]([CH:25]=1)[C:23]#[N:24].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>O.CN(C)C=O>[C:23]([C:22]1[CH:25]=[C:18]([NH:17][C:14]([C:10]2[CH:11]=[C:12]([CH3:13])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=2)=[O:16])[CH:19]=[CH:20][C:21]=1[O:26][CH2:27][C:28]([CH3:30])([CH3:29])[CH3:31])#[N:24]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 178227345-Amino-2-neopentyloxybenzonitrileHCID 222279451-(4-fluorophenyl)-5-methyl-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 22227973N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)-5-methylpyrazole-3-carboxamide수율 49%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

1-(4-Fluorophenyl)-5-methylpyrazole-3-carboxylic acid (2.1 g), 5-amino-2-neopentyloxybenzonitrile (2.0 g), triethylamine (2.9 g) and diethyl cyanophosphate (2.3 g) were added to dimethylformamide (25 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was added into water 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. Methanol was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give the title compound (1.9 g), melting point: 146–147° 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. additionMethanol was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from hydrous methanol

출처 및 근거

ORD 기록
ord-c41a9799799842e39c78a06d82ec2bee
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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