Benzenesulfonyl chloride → HCID 21905219, compound

HRID 1247336Notes

Reaction equation

HRID 1247336 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]([CH2:7][NH:8][C:9](=[O:30])[CH:10]([C:13]2[CH:18]=[C:17]([O:19][CH2:20][CH3:21])[CH:16]=[C:15]([O:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:14]=2[F:29])[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C.CCOC(C)=O>C1COCC1>[C:33]1([S:39]([N:26]2[CH2:25][CH2:24][CH:23]([O:22][C:15]3[C:14]([F:29])=[C:13]([CH:10]([O:11][CH3:12])[C:9]([NH:8][CH2:7][C:6]4[CH:31]=[CH:32][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)=[O:30])[CH:18]=[C:17]([O:19][CH2:20][CH3:21])[CH:16]=3)[CH2:28][CH2:27]2)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21905696HCID 21905696, compound

Product 1

HCID 21905219HCID 21905219, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (RS)-N-(4-cyano-benzyl)-2-[5-ethoxy-2-fluoro-3-(piperidin-4-yloxy)-phenyl]-2-methoxy-acetamide (300 mg) in THF (3 ml) were added benzenesulfonyl chloride (127 mg) and triethylamine (138 mg). The mixture was stirred over the weekend. Ice-water and EtOAc were added and the pH of the aqueous phase was adjusted to 2. The mixture was extracted with EtOAc. The organic phase was washed with saturated NaHCO3 soln. and water, dried, filtered and evaporated to give (RS)-2-[3-(1-benzenesulfonyl-piperidin-4-yloxy)-5-ethoxy-2-fluoro-phenyl]-N-(4-cyano-benzyl)-2-methoxy-acetamide (396 mg) as an off-white solid. MS 582.2 ([M+H]+).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic phase was washed with saturated NaHCO3 soln
  3. dry with materialand water, dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b7149fe4cffa40b8ad2f092e57f4975f
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

Loading…