Sodium Hydroxide → N-{3-Cyano-4-[4-(N-(2-hydroxyethyl)amino)piperidin-1-yl]phenyl}-1-(4-trifluoromethylphenyl)-5-methylpyrazole-4-carboxamide

HRID 1744626ノート

反応式

HRID 1744626 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[CH:11]=[N:10]2)=[CH:5][CH:4]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH2:34][CH2:33][CH:32]([N:35]([CH2:43][CH2:44][OH:45])C(OC(C)(C)C)=O)[CH2:31][CH2:30]2)=[C:25]([CH:28]=1)[C:26]#[N:27].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:26]([C:25]1[CH:28]=[C:21]([NH:20][C:15]([C:12]2[CH:11]=[N:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=3)[C:13]=2[CH3:14])=[O:17])[CH:22]=[CH:23][C:24]=1[N:29]1[CH2:30][CH2:31][CH:32]([NH:35][CH2:43][CH2:44][OH:45])[CH2:33][CH2:34]1)#[N:27]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 107784295-methyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acidHCID 222280265-amino-2-[4-(N-tert-butoxycarbonyl-2-hydroxyethylamino)piperidin-1-yl]benzonitrile

生成物 1

HCID 22228210N-{3-Cyano-4-[4-(N-(2-hydroxyethyl)amino)piperidin-1-yl]phenyl}-1-(4-trifluoromethylphenyl)-5-methylpyrazole-4-carboxamide収率 9.2%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

The reaction and treatment in the same manner as in Example 64 were conducted using 1-(4-trifluoromethylphenyl)-5-methylpyrazole-4-carboxylic acid (1.94 g) and 5-amino-2-[4-(N-tert-butoxycarbonyl-2-hydroxyethylamino)piperidin-1-yl]benzonitrile (2.59 g) and the resulting mixture was further stirred in trifluoroacetic acid (10 ml) under ice-cooling for 1 h. The reaction mixture was treated with aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from a mixed solvent of dimethylformamide-water to give the title compound (0.34 g), melting point: 202° C.

後処理

  1. customThe reaction and treatment in the same manner as in Example 64
  2. temperaturecooling for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of dimethylformamide-water

出典と根拠

ORDレコード
ord-9eeb5718510a45458bb1e8b1e7a62836
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

反応ノート

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