Morpholine → HCID 10433849, compound

HRID 2376867Notes

Reaction equation

HRID 2376867 reaction equation
[CH:1]1([NH:6][C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([N:25]([C:35]([O:37]C5C=CC=CC=5)=O)C(=O)OC5C=CC=CC=5)[CH:20]=4)=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>CN(C)C=O>[CH:1]1([NH:6][C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:35]([N:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)=[O:37])[CH:20]=4)=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 21949107HCID 21949107, compound

Product 1

HCID 10433849HCID 10433849, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl N-(4-(1-cyclopentylaminocarbonyl-1H-indol-5-yloxy)-2-pyridyl)-N-(phenoxycarbonyl)carbamate (200 mg, 0.35 mmol) was dissolved in N,N-dimethylformamide (1.5 ml) and morpholine (0.15 ml, 1.73 mmol); and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia BW-300; ethyl acetate, ethyl acetate:methanol=10:1 in this order); the obtained colorless oil was crystallized by addition of diethyl ether; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound as colorless crystals (140 mg, 0.31 mmol, 90%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washand the organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Fuji Silysia BW-300
  6. customthe obtained colorless oil was crystallized by addition of diethyl ether
  7. filtrationand the crystals were filtered off
  8. washwashed with diethyl ether
  9. customdried under aeration

Sources & evidence

ORD record
ord-f0e4ce72241744e8b46f3249e2e7dbaf
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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