Benzenesulfonyl chloride → N-{5-[4-Methyl-5-(2-methyl-benzoyl)-thiazol-2-ylamino]-pentyl}-benzenesulfonamide

HRID 2119601Notes

Reaction equation

HRID 2119601 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[S:10][C:11]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[O:16])=[C:12]([CH3:14])[N:13]=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(CC)CC>C(O)C>[CH3:14][C:12]1[N:13]=[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2][S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])[S:10][C:11]=1[C:15](=[O:16])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 23442618HCID 23442618, compound

Product 1

HCID 23442564N-{5-[4-Methyl-5-(2-methyl-benzoyl)-thiazol-2-ylamino]-pentyl}-benzenesulfonamideYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 18 mg (0.05 mmol) [2-(5-Amino-pentylamino)-4-methyl-thiazol-5-yl]-o-tolyl-methanone hydrochloride in 1 ml ethanol was treated with 10.6 mg (0.06 mmol) benzenesulfonylchloride and 21 ml NEt3. The mixture was allowed to stir for 15 h at room temperature and afterwards subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. Evaporation of the product fractions yielded 12.6 mg (55%) of the title compound.

Workup

  1. customHPLC separation on reversed phase
  2. washeluting with an acetonitrile/water gradient
  3. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-a85e35dcc6b44509be9fe61d7b550cd9
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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