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

HRID 1744561

反応式

HRID 1744561 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:27][CH:28]([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:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:12]=2[CH3:13])=[O:16])[CH:19]=[CH:20][C:21]=1[O:26][CH2:27][CH:28]([CH3:29])[CH3:30])#[N:24]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 42702631-(4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acidHCID 193660285-Amino-2-isobutoxybenzonitrile

生成物 1

HCID 9821873N-(3-Cyano-4-isobutoxyphenyl)-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide収率 34.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

1-(4-Fluorophenyl)-5-methylpyrazole-4-carboxylic acid (2 g), 5-amino-2-isobutoxybenzonitrile (1.7 g), triethylamine (2.7 g) and diethyl cyanophosphate (2.2 g) were added to dimethylformamide (20 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. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (1.2 g), melting point: 177–178° C.

後処理

  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. additionDiisopropyl ether was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-b2fd98bfe31741838dc65fa990f303a6
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

関連ノート

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