Morpholine → HCID 44155427, compound

HRID 1694651Notes

Reaction equation

HRID 1694651 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:24][C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)[C:28]([OH:30])=[O:29])=[CH:18][CH:19]=3)[O:14][CH:13]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:34]([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH3:35].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=[O:45].N1CCOCC1.CN(C1C=CC=CN=1)C>C1COCC1.O>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:24][C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)[C:28]([O:30][CH2:35][CH2:34][N:36]4[CH2:39][CH2:40][O:45][CH2:38][CH2:37]4)=[O:29])=[CH:18][CH:19]=3)[O:14][CH:13]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

8

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 23661666CVT-10216

Product 1

HCID 44155427HCID 44155427, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL round bottomed flask 3-[(3-{4-[(methylsulfonyl)amino]phenyl}-4-oxochromen-7-yloxy)methyl]benzoic acid (315.0 mg, 0.677 mmol) was treated with triethylamine (137.0 mg, 1.354 mmol, 2.0 equiv) and 2,4,6-trichlorobenzoyl chloride (198.2 mg, 0.812 mmol, 1.2 equiv) in THF (6 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 1 hour. To the mixture were added a solution of 4-hydroxyethyl)morpholine (133.2 mg, 1.016 mmol, 1.5 equiv) in THF (3 mL) and dimethylaminopyridine (82.7 mg, 0.677 mmol, 1.0 equiv). Again, the mixture was stirred at room temperature for 1 hour. To the mixture were added H2O (50 mL) and the whole was extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (50 mL) and dried with Na2SO4. The solvent was removed under a reduced pressure to give a crude mixture. The crude mixture was purified by a column-chromatography (SiO2=80 g, 2.5% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2) to give 2-morpholinoethyl 3-((3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yloxy)methyl)benzoate as a colorless solid.

Workup

  1. stirringAgain, the mixture was stirred at room temperature for 1 hour
  2. extractionthe whole was extracted with EtOAc (50 mL×3)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under a reduced pressure
  6. customto give a crude mixture
  7. customThe crude mixture was purified by a column-chromatography (SiO2=80 g, 2.5% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1eb55ad4ad2f49958f63c449a9c6c86d
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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