Morpholine → HCID 59191308, compound

HRID 626041Notes

Reaction equation

HRID 626041 reaction equation
[CH2:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]3=[O:20])=[CH:10][C:9]=2[F:21])=[C:5]([O:24][CH3:25])[CH:4]=1)[CH3:2].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(#N)C>[CH2:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:18](=[O:19])[CH2:17][CH2:16][C:15]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:20])=[CH:10][C:9]=2[F:21])=[C:5]([O:24][CH3:25])[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59191285HCID 59191285, compound

Product 1

HCID 59191308HCID 59191308, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To 1-[4-(4-ethyl-2-methoxyphenoxy)-3-fluorophenyl]pyrrolidine-2,5-dione (40.4 mg, 0.12 mmol) were added acetonitrile (120 μL) and morpholine (20 μL, 0.24 mmol). The reaction mixture was stirred at 30° C. for 3 days under argon, then concentrated, dissolved in ethyl acetate, washed with saturated NH4Cl and extracted with ethyl acetate. Combined organic phases were dried over Na2SO4, concentrated in vacuo, to give the title product (45.1 mg; 87%) after purification by preparative TLC (dichloromethane/methanol: 9/1).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with saturated NH4Cl
  4. extractionextracted with ethyl acetate
  5. dry with materialCombined organic phases were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-746034c1f6cc4e339c2121ce0b286556
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

Loading…