Morpholine → HCID 23144481, compound

HRID 1967790Notes

Reaction equation

HRID 1967790 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[S:14][C:13]([NH2:15])=[N:12][C:11]=2[C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:29][C:30](Br)=[O:31].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C1COCC1.O>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:11]1[N:12]=[C:13]([NH:15][C:30](=[O:31])[CH2:29][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[S:14][C:10]=1[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:9]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471Triethylamine2×HCID 61147Bromoacetyl bromideHCID 23144459HCID 23144459, compound

Product 1

HCID 23144481HCID 23144481, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 286 (150 mg, 0.526 mmol) and triethylamine (0.367 mL, 2.63 mmol) were dissolved in THF (4 mL), and bromoacetyl bromide (0.206 mL 2.37 mmol) was added thereto at 0° C., followed by stirring for 1 hour at room temperature. Further, a solution (2 mL) of morpholine (0.689 mL, 7.89 mmol) and triethylamine (1.10 mL, 7.89 mmol) in THF was added thereto at 0° C., followed by stirring for 1 hour at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography to afford the entitled Compound 287 (150 mg, 69%).

Workup

  1. customat 0° C.
  2. customat 0° C.
  3. stirringby stirring for 1 hour at room temperature
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe resulting residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-95181e7dc95f4baca17b36167f4d59a7
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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