4-Methoxybenzenesulfonyl chloride → 4-methoxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

HRID 1827528Notes

Reaction equation

HRID 1827528 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>C(Cl)Cl>[CH3:37][O:38][C:39]1[CH:40]=[CH:41][C:42]([S:45]([N:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:14][CH:13]=2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)=[CH:19][CH:18]=2)(=[O:47])=[O:46])=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 22137309[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 221374154-methoxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (1.40 g, 3.53 mmol) and triethylamine (1.48 mL, 10.59 mmol) in methylene chloride (35 mL) was added 4-methoxy-benzenesulfonyl chloride (1.46 g, 7.06 mmol) in three portions over 15 minutes. The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was quenched with saturated sodium bicarbonate and the aqueous solution was washed with methylene chloride. The combined organic solutions were dried (magnesium sulfate), filtered, and concentrated. Medium pressure chromatography using a solvent gradient (4% to 10% methanol/methylene chloride) afforded the title compound of Step A. MS 483.1 (M+1)+

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate
  2. washthe aqueous solution was washed with methylene chloride
  3. dry with materialThe combined organic solutions were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-68728c18ea05442bbb49fc9532698969
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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