Morpholine → 9-{2-Methoxy-5-[6-(morpholin-4-ylcarbonyl)pyridin-2-yl]phenyl}-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

HRID 873516Notes

Reaction equation

HRID 873516 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[CH:24]1[C:37]2[C:36](=[O:38])[CH2:35][C:34]([CH3:40])([CH3:39])[CH2:33][C:32]=2[O:31][C:30]2[CH2:29][C:28]([CH3:42])([CH3:41])[CH2:27][C:26](=[O:43])[C:25]1=2.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C:21]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:22])[N:20]=2)=[CH:11][C:10]=1[CH:24]1[C:25]2[C:26](=[O:43])[CH2:27][C:28]([CH3:41])([CH3:42])[CH2:29][C:30]=2[O:31][C:32]2[CH2:33][C:34]([CH3:40])([CH3:39])[CH2:35][C:36](=[O:38])[C:37]1=2

Participants

7

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 117700629HCID 117700629, compound

Product 1

HCID 1177009089-{2-Methoxy-5-[6-(morpholin-4-ylcarbonyl)pyridin-2-yl]phenyl}-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dioneYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Morpholine (0.0625 ml, 0.72 mmol) was added to a solution of the 6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylic acid produced in Example 1-2 (180 mg, 0.36 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg, 0.72 mmol), and 1-hydroxybenzotriazole monohydrate (55.0 mg, 0.36 mmol) in DMF (4 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 24.5 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was washed with water, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (ethyl acetate). The solid thus obtained was washed with a mixed solution of diethyl ether and hexane, followed by collection by filtration and drying, to obtain the title compound (161 mg, yield: 79%).

Workup

  1. customthe mixture thus obtained
  2. extractionthe mixed solution was then extracted with ethyl acetate
  3. customThe organic layer thus obtained
  4. washwas washed with water
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue thus obtained
  8. customwas then purified by silica gel column chromatography (ethyl acetate)
  9. customThe solid thus obtained
  10. washwas washed with a mixed solution of diethyl ether and hexane
  11. filtrationfollowed by collection by filtration
  12. customdrying

Sources & evidence

ORD record
ord-4f19ced561fd4e1d805f0c7cba92db25
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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