Triethylamine → HCID 76283885, compound

HRID 1480366Notes

Reaction equation

HRID 1480366 reaction equation
CO[C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1[O:7][CH3:8].C(N(CC)CC)C.[CH3:18][NH:19][CH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=2)=[O:29])[CH2:24][CH2:23]1>CO>[CH3:8][O:7][C:6]1[C:5](=[O:9])[C:4](=[O:10])[C:3]=1[N:19]([CH3:18])[CH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=2)=[O:29])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 86722625HCID 86722625, compound

Product 1

HCID 76283885HCID 76283885, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,4-dimethoxycyclobut-3-ene-1,2-dione (20.58 mg, 0.145 mmol) and triethylamine (81 μl, 0.579 mmol) in MeOH (483 μl) was warmed to 45° C. for 30 mins. 3,5-Dichlorobenzyl 4-(2-(methylamino)ethyl)piperidine-1-carboxylate (Example 1, step 3) (50 mg, 0.145 mmol) was added drop wise and the reaction mixture was stirred at room temperature for 18 hours. The resulting mixture was concentrated under reduced pressure and the crude oily product was dissolved in water and extracted with EtOAc. The organic portion was dried over MgSO4, filtered and solvent concentrated under reduced pressure. The crude product was suspended in MeOH and sonicated. The resulting white solid was filtered and dried to afford the title compound;

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. dissolutionthe crude oily product was dissolved in water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationsolvent concentrated under reduced pressure
  7. customsonicated
  8. filtrationThe resulting white solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-c3cc0f5edc934d0280bdfc1f44c2dbe9
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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