Pyridine → HCID 22181912, compound

HRID 1690695Notes

Reaction equation

HRID 1690695 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl.O1CCCC1.C(OCC)(=O)C>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 3128905-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 22181912HCID 22181912, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A sample of 5-Amino-indan-1-one (100 mg, 0.68 mmol) is treated with a solution pyridine (59 mg, 0.75 mmol) in a mixture of dichloromethane (1.5 mL) and tetrahydrofuran (1.5 mL). The reaction is then cooled in an ice bath. A solution of methanesulfonyl chloride (86 mg, 0.75 mmol) in tetrahydrofuran (1.5 mL) is added dropwise and the reaction is allowed to stir for 2 hours at ice bath temperature and overnight at room temperature. The reaction is diluted with ethyl acetate and extracted twice with 1 M HCl. The organics are dried over MgSO4 and the solvent is removed to afford the title material (64 mg, 42% yield) which is not purified but carried on as is: LC/MS calculated for [M+H]+ C10H11NO3S: 226.0, found: 226.0.

Workup

  1. temperatureThe reaction is then cooled in an ice bath
  2. extractionextracted twice with 1 M HCl
  3. dry with materialThe organics are dried over MgSO4
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-5ee10a6bf0c8427d9ed7b5056fd4c939
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

Loading…