Morpholine → HCID 59750801, compound

HRID 748751Notes

Reaction equation

HRID 748751 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:18]([C:21]1[CH:26]=[CH:25][C:24](F)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CN1CCCCC1>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:18]([C:21]1[CH:22]=[CH:23][C:24]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:25][CH:26]=1)(=[O:19])=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 12291N-MethylpiperidineHCID 59750771HCID 59750771, compound

Product 1

HCID 59750801HCID 59750801, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a dimethylsulfoxide (0.5 ml) solution of the 1,4-difluoro-2-[1-[(4-fluorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]benzene (40 mg, 0.095 mmol) obtained in Example 160 were successively added morpholine (0.012 ml, 0.14 mmol) and 1-methylpiperidine (0.017 ml, 0.14 mmol). The resulting mixture was allowed to stand at 80° C. for 24 hours. The reaction mixture was purified by preparative high performance liquid chromatography (using a mixed solvent of water/acetonitrile/formic acid). The resulting solid was washed with diethyl ether and collected by filtration, whereby the title compound (43 mg, 0.088 mmol, 92%) was obtained as a white powder.

Workup

  1. customThe reaction mixture was purified by preparative high performance liquid chromatography (
  2. washThe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-553f0d521928413a901029c2adee166b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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