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

HRID 478626Notes

Reaction equation

HRID 478626 reaction equation
[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][CH3:30])[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]([CH2:29][CH3:30])[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]

Participants

5

Reactant 4

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

Product 1

HCID 10200838N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-ethyl-piperazin-1-yl)-benzamide

Procedure

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (0.9 mmol) 4-(4-ethyl-piperazin-1-yl)-benzoic acid hydrochloride (0.9 mmol), HOBT (0.9 mmol), WSCD (0.9 mmol) and triethylamine (0.9 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 purified by flash chromatography on silica gel with CH2Cl2/MeOH (with 3N NH3)=93:7 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 white powder is obtained.

Workup

  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 (with 3N NH3)=93:7 as mobile phase
  8. additionThe product containing fractions
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA white powder is obtained

Sources & evidence

ORD record
ord-380b1d8cec3d4a95970237783496ed68
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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