4-Methylmorpholine → HCID 15672436, compound

HRID 1645749Notes

Reaction equation

HRID 1645749 reaction equation
CN1CCOCC1.[C:8]([NH:12][C:13]([C:15]1[N:16]=[C:17]([O:23][CH3:24])[S:18][C:19]=1[C:20](O)=[O:21])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl>[C:8]([N:12]1[C:20](=[O:21])[C:19]2[S:18][C:17]([O:23][CH3:24])=[N:16][C:15]=2[C:13]1=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 79724-MethylmorpholineHCID 15672432HCID 15672432, compound

Product 1

HCID 15672436HCID 15672436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.75 g (37.1 mmol) of N-methylmorpholine, 1.20 g (10 mmol) of 4-N,N-dimethylaminopyridine and 8.70 g of a 50% strength solution (13.7 mmol) of propanephosphonic anhydride in CH2Cl2 were added in succession to a solution of 2.6 g (10 mmol) of 4-tert-butylaminocarbonyl-2-methoxythiazole-5-carboxylic acid in 100 ml of CH2Cl2 at -5° C. The mixture was refluxed for 6 hours, after which the solvent was removed and the residue was taken up with ethyl acetate. The solution was extracted twice with saturated sodium bicarbonate solution and once with 5% strength citric acid solution, washed with water and dried over MgSO4. After removal of the solvent, the crude product was purified by chromatography over silica gel (eluant: 1:1 cyclohexane/ethyl acetate) and 1.20 g (50%) of product of melting point 63°-66° C. were obtained in this manner (Active ingredient Example No. 4.014).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customafter which the solvent was removed
  3. extractionThe solution was extracted twice with saturated sodium bicarbonate solution and once with 5% strength citric acid solution
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent
  7. customthe crude product was purified by chromatography over silica gel (eluant: 1:1 cyclohexane/ethyl acetate) and 1.20 g (50%) of product of melting point 63°-66° C.

Sources & evidence

ORD record
ord-f8b366de7784497ead36fb48dfa8224c
Source dataset
uspto-grants-1993_01
Patent number
US05176739

Reaction notes

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