Water → 4-(2-Isopropylaminoethylamino)benzenesulfonic acid 2-(cyclopentanecarbonyl-amino)benzothiazol-6-yl ester

HRID 1867990Notes

Reaction equation

HRID 1867990 reaction equation
CO[CH2:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][S:17]([C:20]3[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5].[CH:27]([NH:30][CH2:31][CH2:32][NH2:33])([CH3:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[CH:3]1([C:4]([NH:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][S:17]([C:20]4[CH:21]=[CH:22][C:23]([NH:33][CH2:32][CH2:31][NH:30][CH:27]([CH3:29])[CH3:28])=[CH:24][CH:25]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:12][CH2:10][CH2:9][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 88098N-IsopropylethylenediamineHCID 579808544-Fluorobenzenesulfonic acid 2-(2-methoxy-acetylamino)benzothiazol-6-yl ester2×

Product 1

HCID 579808394-(2-Isopropylaminoethylamino)benzenesulfonic acid 2-(cyclopentanecarbonyl-amino)benzothiazol-6-yl esterYield 48.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-(2-methoxyacetylamino)-benzothiazol-6-yl ester (intermediate 68) (90 mg, 0.214 mmol), N-isopropylethylenediamine (65.6 mg, 0.642 mmol) and cesium carbonate (69.7 mg, 0.214 mmol) in 2 ml of dimethyl sulfoxide in a test tube, equipped with a magnetic bar, is stirred overnight at 80° C. 100 ml of water are added and the reaction medium is extracted with ethyl acetate. The organic phase is then washed with water, dried over magnesium sulfate and evaporated. The residue, purified by LC/MS, gives 26.2 mg of 4-(2-isopropylaminoethylamino)benzenesulfonic acid 2-(cyclopentanecarbonyl-amino)benzothiazol-6-yl ester (white powder) in a yield of 24%.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is then washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue, purified by LC/MS

Sources & evidence

ORD record
ord-5b5b3b01394f45129a079e55ce8a809f
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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