Benzenesulfonamide → HCID 57584955, compound

HRID 2077506Notes

Reaction equation

HRID 2077506 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:14]1[N:19]=[C:18]([C:20]2[CH:32]=[CH:31][C:23]3[N:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[S:26][C:22]=3[CH:21]=2)[CH:17]=[CH:16][N:15]=1>CS(C)=O>[C:1]1([S:7]([NH:10][C:14]2[N:19]=[C:18]([C:20]3[CH:32]=[CH:31][C:23]4[N:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[S:26][C:22]=4[CH:21]=3)[CH:17]=[CH:16][N:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 57584955HCID 57584955, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Benzenesulfonamide (150 mg, 0.954 mmol) was dissolved in DMSO (1.5 mL) and NaH (56.1 mg, 1.40 mmol, 60% in mineral oil) was added, and the reaction mixture was stirred at RT for 1 hour. N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (50.2 mg, 0.165 mmol) was added, and the reaction flask was placed in a preheated oil bath (125° C.) and stirred under nitrogen. The reaction was stirred for 21 hours, and then cooled to RT and quenched with MeOH. The suspension was filtered through a pad of Celite® (diatomaceous earth), which was washed with DCM and MeOH, and the filtrate was concentrated, and purified on an HPLC system (10-95% MeCN/water with 0.1% TFA over 30 minutes) to provide N-(6-(2-(phenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (29 mg, 41%). MS (ESI pos. ion) m/z: 426 (MH+). Calculated exact mass for C19H5N5O3S2: 425. 1H NMR (400 MHz, DMSO-d6): 12.53 (s, 1H), 8.54-8.56 (m, 2H), 8.09 (d, J=9.0 Hz, 1H), 8.05 (d, J=7.5 Hz, 2H), 7.83 (d, J=8.5 Hz, 1H), 7.58-7.63 (m, 4H), 2.24 (s, 3H).

Workup

  1. customthe reaction flask was placed in a preheated oil bath
  2. stirring(125° C.) and stirred under nitrogen
  3. stirringThe reaction was stirred for 21 hours
  4. temperaturecooled to RT
  5. customquenched with MeOH
  6. filtrationThe suspension was filtered through a pad of Celite® (diatomaceous earth), which
  7. washwas washed with DCM and MeOH
  8. concentrationthe filtrate was concentrated
  9. custompurified on an HPLC system (10-95% MeCN/water with 0.1% TFA over 30 minutes)

Sources & evidence

ORD record
ord-761b7e5b1a0d43fe992aadfb7c6e0e66
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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