Cyclopropylamine → HCID 178471878, compound

HRID 1770110Notes

Reaction equation

HRID 1770110 reaction equation
[CH3:1][O:2][C:3]1[C:4]([F:23])=[C:5]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:6]([C:8](=[CH:14]OCC)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].[CH:24]1([NH2:27])[CH2:26][CH2:25]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([F:23])=[C:5]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:6]([C:8](=[CH:14][NH:27][CH:24]1[CH2:26][CH2:25]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 54548840Ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate

Product 1

HCID 178471878HCID 178471878, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-(3-methoxy-2,4,5-triflurobenzoyl)-3-ethoxyacrylate (590 mg, 1.8 mmol) in methylene chloride (15 mL) at 0° C. was added a solution of cyclopropylamine (114 mg, 1.98 mmol, 1.2 equiv) in methylene chloride (5 mL). The reaction mixture was warmed to room temperature and allowed to stir for 2 hours. The solvent was removed in vacuo and the crude concentrate was purified by flash chromatography on silica gel (methylene chloride/ethyl acetate 50:1 v/v) to provide 438 mg, 62% yield over two steps, of a viscous yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. concentrationthe crude concentrate
  3. customwas purified by flash chromatography on silica gel (methylene chloride/ethyl acetate 50:1 v/v)
  4. customto provide 438 mg, 62% yield over two steps

Sources & evidence

ORD record
ord-27d501a88f064ef29ddb9af5a39978a7
Source dataset
uspto-grants-1995_01
Patent number
US05385913

Reaction notes

Loading…