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

HRID 18429

Reaction equation

HRID 18429 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.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([NH: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)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11515729N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

Product 1

HCID 11669000N-[5-(3-{[(methylsulfonyl)amino]methyl}phenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideYield 55%

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 methanesulfonyl chloride (25 mg, 0.22 mmol) and the wole mix stirred at room temperature under argon for 1 h. The reaction mix was washed with 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 yellow oil (46 mg, 55%).

Workup

  1. additionthe wole mix
  2. additionThe reaction mix
  3. washwas washed with 0.5M hydrochloric acid
  4. customthe organic layer was evaporated under reduced pressure
  5. customto give a brown oil which
  6. customwas purified by column chromatography on a 1 g SCX column
  7. washeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-8db9dd41d11c4b72a71329da174e1868
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Linked notes

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