2-(2-Bromoethoxy)tetrahydro-2H-pyran → HCID 71251922, compound

HRID 2411814Notes

Reaction equation

HRID 2411814 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1.Br[CH2:29][CH2:30][O:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH2:29][CH2:30][O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=2)=[O:16])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 39847681HCID 39847681, compound

Product 1

HCID 71251922HCID 71251922, compound

Procedure

Using N-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}methanesulfonamide (271 mg) described in Example 461 and 2-(2-bromoethoxy)tetrahydropyran (1.21 mL) and by the reaction and treatment in the same manner as in Example 36, N-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-N-[2-(tetrahydropyran-2-yloxy)ethyl]methanesulfonamide was obtained. The obtained N-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}-N-[2-(tetrahydropyran-2-yloxy)ethyl]methanesulfonamide was dissolved in methanol (5 mL), p-toluenesulfonic acid 1 hydrate (121 mg) was added, and the mixture was stirred at room temperature. To the reaction mixture was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (185 mg).

Sources & evidence

ORD record
ord-cdef8af45c83491eb633e9cafc7fd9b6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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