Water → 4-(2-Isopropylaminoethylamino)benzenesulfonic acid 2-acetylaminobenzothiazol-6-yl ester

HRID 1867987Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([O:14][S:15]([C:18]3[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].[CH:25]([NH:28][CH2:29][CH2:30][NH2:31])([CH3:27])[CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([O:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:31][CH2:30][CH2:29][NH:28][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-acetylaminobenzothiazol-6-yl ester (intermediate 64) (66 mg, 0.180 mmol), N-isopropylethylenediamine (55.2 mg, 0.540 mmol) and cesium carbonate (58.6 mg, 0.180 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 43 mg of 4-(2-isopropylaminoethylamino)benzenesulfonic acid 2-acetylaminobenzothiazol-6-yl ester (white powder) in a yield of 53%.

Workup

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

Sources & evidence

ORD record: ord-337a1e80b41c441cb15c49afe1f533f2
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632952B2

Reaction notes

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