Morpholine → HCID 23144213, compound

HRID 1967759Notes

Reaction equation

HRID 1967759 reaction equation
[C:1]([C:4]1[S:8][C:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[O:11])=[N:6][C:5]=1[C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)([OH:3])=O.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[O:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[C:5]1[N:6]=[C:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[O:11])[S:8][C:4]=1[C:1]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:3]

Participants

8

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23144495HCID 23144495, compound

Product 1

HCID 23144213HCID 23144213, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 95 (410 mg, 1.30 mmol), morpholine (0.141 mL, 1.60 mmol), EDC hydrochloride (500 mg, 2.60 mmol), 1-hydroxybenzotriazole monohydrate (400 mg, 2.60 mmol) and triethylamine (0.36 mL, 2.60 mmol) were dissolved in DMF (5 mL), followed by stirring at room temperature for 3 hours. Water was added to the reaction mixture, followed by extraction with chloroform. 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 recrystallized from ethanol to afford the entitled Compound 96 (159 mg, 34%) as colorless crystals.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7a601133c6b54ac5a5caaf13bf3cea2b
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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