Morpholine → N-[5-(4,4-Dimethyl-2,5-dioxo-3-pyridin-4-ylmethyl-imidazolidin-1-yl)-2-trifluoromethoxy-phenyl]-2-morpholin-4-yl-acetamide

HRID 2356934Notes

Reaction equation

HRID 2356934 reaction equation
[CH3:1][C:2]1([CH3:32])[C:6](=[O:7])[N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:19][C:20]([F:23])([F:22])[F:21])=[C:12]([NH:14][C:15](=[O:18])[CH2:16]Cl)[CH:13]=2)[C:4](=[O:24])[N:3]1[CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[CH3:1][C:2]1([CH3:32])[C:6](=[O:7])[N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:19][C:20]([F:23])([F:22])[F:21])=[C:12]([NH:14][C:15](=[O:18])[CH2:16][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH:13]=2)[C:4](=[O:24])[N:3]1[CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 23110283N-[5-(4,4-Dimethyl-2,5-dioxo-3-pyridin-4-ylmethyl-imidazolidin-1-yl)-2-trifluoromethoxy-phenyl]-2-chloro-acetamide

Product 1

HCID 11642143N-[5-(4,4-Dimethyl-2,5-dioxo-3-pyridin-4-ylmethyl-imidazolidin-1-yl)-2-trifluoromethoxy-phenyl]-2-morpholin-4-yl-acetamide

Procedure

50 mg N-[5-(4,4-Dimethyl-2,5-dioxo-3-pyridin-4-ylmethyl-imidazolidin-1-yl)-2-trifluoromethoxy-phenyl]-2-chloro-acetamide (raw material, as described above) owere dissolved in 2 ml morpholine and heated for 1 h to 50° C. Subsequently, the mixture was poured on ice and extracted with ethylacetate. The combined organic phases were evaporated to dryness and the residue was purified by flash chromoatography (Silica gel, methylene chloride:methanol=1.98:22.95:5) Yield: 20 mg

Workup

  1. temperatureheated for 1 h to 50° C
  2. additionSubsequently, the mixture was poured on ice
  3. extractionextracted with ethylacetate
  4. customThe combined organic phases were evaporated to dryness
  5. customthe residue was purified by flash chromoatography (Silica gel, methylene chloride:methanol=1.98:22.95:5) Yield: 20 mg

Sources & evidence

ORD record
ord-7c4e906c3c6e4cc689578e9045b16fa1
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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