Dimethylformamide → N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-[4-(2-methoxy-ethyl)-piperazin-1-yl]-benzamide

HRID 478638ノート

反応式

HRID 478638 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].Cl.[CH3:15][O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=2C(O)=O)[CH2:21][CH2:20]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CN([CH:54]=[O:55])C>>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:54](=[O:55])[C:31]2[CH:30]=[CH:26][C:25]([N:22]3[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][O:16][CH3:15])[CH2:24][CH2:23]3)=[CH:33][CH:32]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amideHCID 69130178[4-(2-Methoxy-ethyl)-piperazin-1-yl]-benzoic acid hydrochloride

生成物 1

HCID 10296139N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-[4-(2-methoxy-ethyl)-piperazin-1-yl]-benzamide

実験手順

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (1.0 mmol), [4-(2-methoxy-ethyl)-piperazin-1-yl]-benzoic acid hydrochloride (1.0 mmol), HOBT (1.0 mmol), WSCD (1.0 mmol) and triethylamine (1.0 mmol) are dissolved in DMF (4 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 purified by flash chromatography on silica gel with CH2Cl2/MeOH=92.5:7.5 as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale powder with mp. 166-168° C., Rf=0.37 (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. customThe residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH=92.5:7.5 as mobile phase
  8. additionThe product containing fractions
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA pale powder with mp. 166-168° C., Rf=0.37 (CH2Cl2/MeOH=9:1) is obtained

出典と根拠

ORDレコード
ord-75be2bca7afa4d01a498f8e027f5fc61
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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