Triethylamine → HCID 58786857, compound

HRID 1767126Notes

Reaction equation

HRID 1767126 reaction equation
[C:1]([C:3]1([CH3:26])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])#[N:2].CCN(CC)CC.[NH2:34][OH:35].Cl.[CH3:37][O:38][C:39]([C:41]#[C:42][C:43]([O:45][CH3:46])=[O:44])=[O:40]>CCO>[NH2:2]/[C:1](=[N:34]\[O:35]/[C:42](/[C:43]([O:45][CH3:46])=[O:44])=[CH:41]/[C:39]([O:38][CH3:37])=[O:40])/[C:3]1([CH3:26])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12980Dimethyl acetylenedicarboxylateHCID 443297Hydroxyamine hydrochlorideHCID 21098156HCID 21098156, compound

Product 1

HCID 58786857HCID 58786857, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 1-benzyl 4-tert-butyl 2-cyano-2-methylpiperazine-1,4-dicarboxylate (C-41) in EtOH was added to a solution of Et3N (3.2 eq) and NH2OH HCl (3 eq) in EtOH. The mixture was stirred 2 hr at 40° C. After evaporation of the solvent, the residue was diluted with AcOEt, washed with water, dried over Na2SO4, filtered and concentrated. The residue was further dissolved in chloroform and dimethylacetylenedicarboxylate (1.5 eq) added to the stirred solution. Reaction was refluxed over night. The mixture was evaporated and the residue was purified by flash chromatography on silica gel (petroleum ether/AcOEt, 65:35) affording (C-42).

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with AcOEt
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was further dissolved in chloroform
  8. customReaction
  9. temperaturewas refluxed over night
  10. customThe mixture was evaporated
  11. customthe residue was purified by flash chromatography on silica gel (petroleum ether/AcOEt, 65:35)
  12. customaffording (C-42)

Sources & evidence

ORD record
ord-5db248216d814ea7a901197ea16222e1
Source dataset
uspto-grants-2007_06
Patent number
US07232819B2

Reaction notes

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