4-Toluenesulfonyl chloride → HCID 69146432, compound

HRID 2223904Notes

Reaction equation

HRID 2223904 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:20])[CH2:14][CH2:13]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.N12CCN(CC1)CC2.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>ClCCl>[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([NH:1][CH2:2][CH2:3][C:4]2([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([N:18]([C:26]4[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=4)[C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)=[O:20])[CH2:14][CH2:13]3)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)(=[O:49])=[O:48])=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 23109894HCID 23109894, compound

Product 1

HCID 69146432HCID 69146432, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-[2-[1-(2-aminoethyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (synthesized in Example 18) (228 mg) in dichloromethane (3 mL) were added 1,4-diazabicyclo[2.2.2]octane (108 mg) and p-toluenesulfonyl chloride (120 mg) successively. The solution was stirred at room temperature for 6 hours. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3 to 1:2)] to give the title compound (265 mg).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3 to 1:2)]

Sources & evidence

ORD record
ord-e21a2b21cd404e4eaeeef8e5ab0d29b9
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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