Triethylamine → HCID 57033160, compound

HRID 278986Notes

Reaction equation

HRID 278986 reaction equation
[CH2:1]([O:4][N:5]1[C:14](=[O:15])[C:13]2[C:16]([Cl:20])=[CH:17][C:18](Cl)=[C:11]3[C:12]=2[C:7](=[CH:8][CH:9]=[C:10]3[Cl:21])[C:6]1=[O:22])[CH:2]=[CH2:3].[C:23]([O:27][C:28](=[O:35])[NH:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C>C(#N)C>[C:23]([O:27][C:28](=[O:35])[NH:29][C@H:30]1[CH2:34][CH2:33][N:32]([C:18]2[CH:17]=[C:16]([Cl:20])[C:13]3[C:14](=[O:15])[N:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:6](=[O:22])[C:7]4[C:12]=3[C:11]=2[C:10]([Cl:21])=[CH:9][CH:8]=4)[CH2:31]1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 22623918HCID 22623918, compound

Product 1

HCID 57033160HCID 57033160, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-allyloxy-4,6,7-trichlorobenzo[de]isoquinoline-1,3-dione (0.44 g, 1.2 mmol, from Example I4), (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (0.3 g, 1.5 mmol), triethylamine (0.2 g, 2.0 mmol), and 20 mL of acetonitrile was stirred at room temperature for 6 hours. The solvent was removed in vacuo and the residue partitioned between water and dichloromethane. The organic layer was dried and evaporated in vacuo. The residue was chromatographed on silica gel (ICN 230-400 mesh) eluting with dicholromethane/ethyl acetate (80:20) to give 0.35 g of the title compound, mp 123-125° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water and dichloromethane
  3. customThe organic layer was dried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (ICN 230-400 mesh)
  6. washeluting with dicholromethane/ethyl acetate (80:20)

Sources & evidence

ORD record
ord-7f7342dab9b44a1a86fcafcf3b309657
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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