Phosphate → 4-Methyl-N-{3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-benzenesulfonamide

HRID 2119609Notes

Reaction equation

HRID 2119609 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[S:7][C:8]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[O:12])=[CH:9][N:10]=1.C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.P([O-])([O-])([O-])=O>ClCCl>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]2[S:7][C:8]([C:11](=[O:12])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[CH:9][N:10]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23442548[2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone

Product 1

HCID 234427514-Methyl-N-{3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone was dissolved in dichloromethane and triethylamine and toluene-4-sulfonyl chloride added. The mixture was stirred overnight at room temperature, poured into 1 M pH4 phosphate buffer (5 ml) and extracted with dichloromethane (3×10 ml). The combined organic phases were dried over magnesium sulfate and evaporated. The oily residue was purified by column chromatography on silica gel (13:7 hexane/acetone eluant), using a small amount of dichloromethane to apply the mixture to the column. The title compound was isolated as an off-white solid. MS (m/e): 428.3 (M−H, 100%).

Workup

  1. extractionextracted with dichloromethane (3×10 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customevaporated
  4. customThe oily residue was purified by column chromatography on silica gel (13:7 hexane/acetone eluant)

Sources & evidence

ORD record
ord-c086feba8a8542a4ad3785d7527d90cf
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

Loading…