Morpholine → HCID 23144522, compound

HRID 1967814Notes

Reaction equation

HRID 1967814 reaction equation
[CH:1]1([C:4]([C:6]2[S:10][C:9]([NH2:11])=[N:8][C:7]=2[C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[O:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:25][C:26](Br)=[O:27].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C1COCC1.O>[CH:1]1([C:4]([C:6]2[S:10][C:9]([NH:11][C:26](=[O:27])[CH2:25][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[N:8][C:7]=2[C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[O:5])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471Triethylamine2×HCID 61147Bromoacetyl bromideHCID 86060938HCID 86060938, compound

Product 1

HCID 23144522HCID 23144522, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 419 (192 mg, 0.824 mmol) and triethylamine (0.379 mL, 2.72 mmol) were dissolved in THF (4 mL), and bromoacetyl bromide (0.215 mL, 2.47 mmol) was added thereto at 0° C., followed by stirring at room temperature for 1 hour. At 0° C., a solution (2 mL) of morpholine (1.08 mL, 12.4 mmol) in THF and triethylamine (1.73 mL, 12.4 mmol) was added to the reaction mixture, followed by stirring at room temperature for 1 hour. 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 421 (229 mg, 77%).

Workup

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

Sources & evidence

ORD record
ord-deffaa29b4864c7c936084d392529213
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

Loading…