Toluene → HCID 178471881, compound

HRID 477826Notes

Reaction equation

HRID 477826 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][N:9]([C:11]2[C:24]([F:25])=[CH:23][C:14]([C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[C:13]([F:26])[C:12]=2[F:27])[CH2:8][CH2:7][O:6]1)[CH3:3].CO[CH:30](OC)[N:31]([CH3:33])C.[C:36]1(C)C=CC=C[CH:37]=1>>[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][N:9]([C:11]2[C:24]([F:25])=[CH:23][C:14]([C:15]([C:17](=[CH:33][NH:31][CH:30]3[CH2:37][CH2:36]3)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[C:13]([F:26])[C:12]=2[F:27])[CH2:8][CH2:7][O:6]1)[CH3:3]

Participants

4

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 19834973Ethyl 4-[2-(dimethylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetate

Product 1

HCID 178471881HCID 178471881, compoundYield 89%

Procedure

A solution of 3.88 g of ethyl 4-[2-(dimethylaminomethyl)-morpholino]-2,3,5-trifluorobenzoylacetate and 1.85 g of dimethylformamide dimethylacetal in 20 ml of toluene is refluxed for 6 hours. The reaction mixture is concentrated under reduced pressure and to the obtained residue is added 20 ml of ethanol. After the addition of 0.94 g of cyclopropylamine under ice-cooling, the mixture is stirred at room temperature for 3 hours. The reaction mixture is concentrated under reduced pressure and the obtained residue is purified by chromatography on silica gel to give 4.06 g of ethyl 2-[4-[2-(dimethylaminomethyl)morpholino]-2,3,5-trifluorobenzoyl]-3-cyclopropylaminoacrylate in 89% yield as an oily substance.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure and to the obtained residue
  2. additionis added 20 ml of ethanol
  3. additionAfter the addition of 0.94 g of cyclopropylamine under ice-
  4. temperaturecooling
  5. concentrationThe reaction mixture is concentrated under reduced pressure
  6. customthe obtained residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7ef218a4df014769ba8e01f7cf25f87d
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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