1,2-Dichloroethane → HCID 68815111, compound

HRID 1612472Notes

Reaction equation

HRID 1612472 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.[CH3:20][NH:21][CH2:22][CH2:23][CH3:24].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:10]=[C:6]([C:7]([N:21]([CH3:20])[CH2:22][CH2:23][CH3:24])=[O:9])[CH:5]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 12315N-MethylpropylamineHCID 757711-HydroxybenzotriazoleHCID 69358928HCID 69358928, compound

Product 1

HCID 68815111HCID 68815111, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2-Oxo-pyrrolidin-1-yl)-isophthalic acid monomethyl ester (D63) (1.0 g, 3.8 mmol) was dissolved in DMF (7 ml) and treated with N-methyl propylamine (0.42 g, 5.7 mmol), HOBt (0.62 g, 4.56 mmol) and EDC (1.02 g, 5.32 mmol) and the resulting solution was stirred overnight at room temperature. It was then evaporated to dryness and the residue was partitioned between EtOAc and dil.HCl. The organic phase was separated, washed with dil.HCl (×2), dil.NaHCO3 (×3) and brine (×1). It was dried (MgSO4) and evaporated to leave the crude product which was purified by silica chromatography eluting with DCM/MeOH to afford the pure title compound (D64) (0.40 g, 33%).

Workup

  1. customIt was then evaporated to dryness
  2. customthe residue was partitioned between EtOAc
  3. customThe organic phase was separated
  4. washwashed with dil
  5. dry with materialIt was dried (MgSO4)
  6. customevaporated
  7. customto leave the crude product which
  8. customwas purified by silica chromatography
  9. washeluting with DCM/MeOH

Sources & evidence

ORD record
ord-0cd4e0a975e74f07bc0bae74c70304ef
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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