p-Bromobenzenesulfonyl chloride → 4-(4-Bromobenzenesulfonyl)-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinone

HRID 2214833Notes

Reaction equation

HRID 2214833 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12]([NH:14][C:15]1([CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][C:30]2=[O:35])[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=2)[CH2:17][CH2:16]1)=[O:13])[CH3:10].[Br:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:36][C:37]1[CH:42]=[CH:41][C:40]([S:43]([N:32]2[CH2:33][CH2:34][N:29]([CH2:28][C:15]3([NH:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH2:16][CH2:17][N:18]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=4)[CH2:19][CH2:20]3)[C:30](=[O:35])[CH2:31]2)(=[O:45])=[O:44])=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 21948312HCID 21948312, compound

Product 1

HCID 102106674-(4-Bromobenzenesulfonyl)-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinoneYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (400 mg) was added to a solution of 1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinone hydrochloride (440 mg) obtained in Reference Example 11 in dichloromethane (15 ml), 4-bromobenzenesulfonyl chloride (255 mg) was added at 0° C., and the mixture was stirred at room temperature for 1 hour. An aqueous sodium carbonate solution was added to the reaction solution, the material was extracted with dichloromethane, dried, concentrated, and purified by silica gel column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (403 mg) as colorless crystals.

Workup

  1. extractionthe material was extracted with dichloromethane
  2. customdried
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record
ord-a2eb2c7174664d53ad8e435e13acf648
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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