Dimethylformamide → N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-methyl-piperazin-1-yl)-benzamide

HRID 478623ノート

反応式

HRID 478623 の反応式
[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].[CH:14]1[CH:15]=[CH:16][C:17]2[N:22](O)N=N[C:18]=2[CH:19]=1.[CH2:24]([N:26]([CH2:29]C)[CH2:27][CH3:28])[CH3:25].CN([CH:34]=[O:35])C>>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:34](=[O:35])[C:14]2[CH:19]=[CH:18][C:17]([N:22]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:24][CH2:25]3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amide

生成物 1

HCID 10199981N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-methyl-piperazin-1-yl)-benzamide

実験手順

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (1.38 mmol) 4-(4-methyl-piperazin-1-yl)-benzoic acid hydrochloride (1.38 mmol), HOBT (1.38 mmol), WSCD (1.38 mmol) and triethylamine (1.38 mmol) are dissolved in DMF (5 ml) and stirred overnight at rt. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure slightly basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale powder with mp. 218-220° C., Rf=0.19 (CH2Cl2/MeOH=9:1) is obtained.

後処理

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in a mixture of water and sodium carbonate (
  3. extractionextracted three times with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA pale powder with mp. 218-220° C., Rf=0.19 (CH2Cl2/MeOH=9:1) is obtained

出典と根拠

ORDレコード
ord-cbac4d507b4b4d6cafa51a84defb4169
出典データセット
uspto-grants-2003_11
特許番号
US06642239B2

反応ノート

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