Cesium carbonate → HCID 86612155, compound

HRID 1867999Notes

Reaction equation

HRID 1867999 reaction equation
[CH:1]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:25]=[CH:24][C:23](F)=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1.[CH3:27][C:28]1([CH3:38])[N:33]([O])[C:32]([CH3:36])([CH3:35])[CH2:31][CH:30]([NH2:37])[CH2:29]1.C(=O)([O-])[O-:40].[Cs+].[Cs+]>CS(C)=O.O>[CH:1]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:25]=[CH:24][C:23]([NH:37][CH:30]5[CH2:29][C:28]([CH3:38])([CH3:27])[N:33]([OH:40])[C:32]([CH3:36])([CH3:35])[CH2:31]5)=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5509421-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl-2×HCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

Product 1

HCID 86612155HCID 86612155, compoundYield 14.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester (example 7) (0.352 mmol, 138 mg), 4-amino-TEMPO (0.387 mmol, 66 mg) and cesium carbonate (0.352 mmol, 114 mg) in 3.5 ml of dimethylsulfoxide is stirred for 24 hours. 4-Amino-TEMPO is added twice (2 times 66 mg) after 24 and 48 hours. After 48 hours, the reaction is placed at room temperature for 48 hours. The solution is then diluted with water, extracted with ethyl acetate, washed with saturated sodium chloride solution and dried over sodium sulfate, and then evaporated to dryness, to give 258 mg of crude product. This product is purified by flash chromatography on a cartridge of 5 g of silica. The eluents used are, respectively, dichloromethane and then dichloromethane with 1% of 7M 0.01% ammoniacal methanol. 28 mg of 4-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-ylamino)benzenesulfonic acid 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester are obtained in a yield of 14%.

Workup

  1. waitthe reaction is placed at room temperature for 48 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customto give 258 mg of crude product
  7. customThis product is purified by flash chromatography on a cartridge of 5 g of silica

Sources & evidence

ORD record
ord-be5970782e66436c863d724f06c03243
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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