Potassium Carbonate → HCID 90389133, compound

HRID 2203424Notes

Reaction equation

HRID 2203424 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]([C:19]1[S:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([C:44]2[N:49]3[CH:50]=[CH:51][N:52]=[C:48]3[N:47]=[CH:46][CH:45]=2)[CH:38]=1>CS(C)=O.C(OCC)(=O)C.O>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][C:13]2[C:14]([F:16])=[CH:15][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:3]=3[O:2][CH3:1])[C:19]3[S:23][N:22]=[CH:21][N:20]=3)(=[O:8])=[O:9])=[C:11]([F:18])[CH:12]=2)=[C:39]([C:44]2[N:49]3[CH:50]=[CH:51][N:52]=[C:48]3[N:47]=[CH:46][CH:45]=2)[CH:38]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 136508798HCID 136508798, compound

Product 1

HCID 90389133HCID 90389133, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.89 g, 2.0 mmol) and potassium carbonate (0.83 g, 6.0 mmol) in dimethylsulfoxide (15 mL) at ambient temperature was added 4-chloro-2-(imidazo[1,2-a]pyrimidin-5-yl)phenol (0.45 g, 2.0 mmol). The mixture was stirred at ambient temperature for 16 h and diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with a 80-100% gradient of ethyl acetate in hexanes to afford 4-(4-chloro-2-(imidazo[1,2-a]pyrimidin-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.47 g). This solid was dissolved in dichloromethane (15 mL) and trifluoroacetic acid (2 mL) was added. The mixture was stirred for 2 h at ambient temperature and concentrated in vacuo. The residue was triturated in a mixture of ethyl ether and ethyl acetate to afford 4-(4-chloro-2-(imidazo[1,2-a]pyrimidin-5-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a colorless solid in 53% yield (0.55 g): 1H NMR (300 MHz, DMSO-d6) δ8.94 (d, J=4.2 Hz, 1H), 8.52 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.07 (d, J=1.2 Hz, 1H), 7.91-7.69 (m, 3H), 7.61 (d, J=4.2 Hz, 1H), 7.56-7.47 (m, 1H), 7.43 (d, J=8.7 Hz, 1H); MS (ES+) m/z 520.7 (M+1), 522.7 (M+1).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with a 80-100% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-68679ee0ff8e4e548328004377bcbd74
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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