Triethylamine → N-(5-{3-[(2-oxo-1-pyrrolidinyl)methyl]phenyl}-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

HRID 18431Notes

Reaction equation

HRID 18431 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Cl[CH2:33][CH2:34][CH2:35][C:36](Cl)=[O:37].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:37]=[C:36]1[CH2:35][CH2:34][CH2:33][N:1]1[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 11515729N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

Product 1

HCID 11683045N-(5-{3-[(2-oxo-1-pyrrolidinyl)methyl]phenyl}-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamideYield 19.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide (69 mg, 0.2 mmol) in dichloromethane (5 ml) was treated with triethylamine (40 mg, 0.4 mmol), followed by 4-chlorobutanoyl chloride (32 mg, 0.22 mmol) and the whole mix stirred at room temperature under argon for 1 h. The reaction mix was evaporated under reduced pressure to remove the dichloromethane and then dimethylformamide was added (5 ml) followed by potassium carbonate (60 mg, 0.43 mmol) and the mix stirred at 100° C. for 2 h. The reaction mix was cooled then partitioned between dichloromethane and 0.5M hydrochloric acid, and the organic layer was evaporated under reduced pressure to give a brown oil which was purified by column chromatography on a 1 g SCX column eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a beige solid (16 mg, 19%).

Workup

  1. additionthe whole mix
  2. additionThe reaction mix
  3. customwas evaporated under reduced pressure
  4. customto remove the dichloromethane
  5. additiondimethylformamide was added (5 ml)
  6. stirringthe mix stirred at 100° C. for 2 h
  7. additionThe reaction mix
  8. temperaturewas cooled
  9. customthen partitioned between dichloromethane and 0.5M hydrochloric acid
  10. customthe organic layer was evaporated under reduced pressure
  11. customto give a brown oil which
  12. customwas purified by column chromatography on a 1 g SCX column
  13. washeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-9a8a09a287e142e79aaaadf407bc6de2
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Reaction notes

Loading…