4-Toluenesulfonyl chloride → HCID 86599847, compound

HRID 2099026Notes

Reaction equation

HRID 2099026 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:30])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:22][CH2:21]1)[CH:14]=2.CCN(C(C)C)C(C)C.[S:40](Cl)([C:43]1[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=1)(=[O:42])=[O:41].C(=O)(O)[O-].[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:30])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][O:29][S:40]([C:43]3[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[CH2:22][CH2:21]1)[CH:14]=2

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86599848HCID 86599848, compound

Product 1

HCID 86599847HCID 86599847, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

70 mg (0.16 mmol) 3-Benzothiazol-2-yl-7-[4-(3-hydroxy-propyl)-piperazin-1-yl]-chromen-2-one are dissolved in 15 mL dichloromethane under argon. 0.083 mL Hünig base and 10 mg DMAP are added to the stirred solution, followed by 46 mg (1.5 eq.) tosyl chloride. The reaction mixture is stirred for 20 h at room temperature, poured onto ice, treated with 2 mL aqueous sodium bicarbonate solution and extracted (dichloromethane, saline). The organic phase is evaporated and the residue column chromatographed (silica gel, dichloromethane/EtOH 98:2) to yield after evaporation and drying under high vacuum 73 mg (78%) desired product as a light brownish powder.

Workup

  1. additionpoured onto ice
  2. extractionextracted (dichloromethane, saline)
  3. customThe organic phase is evaporated
  4. customthe residue column chromatographed (silica gel, dichloromethane/EtOH 98:2)
  5. customto yield
  6. customafter evaporation
  7. dry with materialdrying under high vacuum 73 mg (78%) desired product as a light brownish powder

Sources & evidence

ORD record
ord-7e3aa44568994649a2ef2db65678e6ec
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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