Potassium Carbonate → HCID 71557022, compound

HRID 2203428Notes

Reaction equation

HRID 2203428 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[N:14][C:13]=23)[CH:3]=1.COC1C=C(OC)C=CC=1C[N:23]([C:36]1[S:40][N:39]=[CH:38][N:37]=1)[S:24]([C:27]1[CH:32]=[C:31]([F:33])[C:30](F)=[CH:29][C:28]=1[F:35])(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:30]2[C:31]([F:33])=[CH:32][C:27]([S:24]([NH:23][C:36]3[S:40][N:39]=[CH:38][N:37]=3)(=[O:25])=[O:26])=[C:28]([F:35])[CH:29]=2)=[C:4]([C:9]2[CH:10]=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[N:14][C:13]=23)[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 89544255HCID 89544255, compound

Product 1

HCID 71557022HCID 71557022, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-chloro-2-(pyrazolo[1,5-a]pyrimidin-3-yl)phenol (0.150 g, 0.61 mmol) and N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.285 g, 0.64 mmol) in dimethylsulfoxide (5 mL) was added potassium carbonate (0.127 g, 0.92 mmol) and the mixture was stirred at ambient temperature for 4 h. The mixture was partitioned between ethyl acetate (100 mL) and water (20 mL). The organic phase was washed with brine (2×10 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue obtained was dissolved in dichloromethane (3 mL) and trifluoroacetic acid (3 mL). The reaction mixture was stirred for 3 h at ambient temperature and concentrated in vacuo. The residue was suspended in a mixture of dichloromethane and methanol (1:1, 50 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo and the residue that was triturated in ethyl acetate to afford 4-(4-chloro-2-(pyrazolo[1,5-a]pyrimidin-3-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a beige solid in 68% yield (0.233 g): 1H NMR (300 MHz, DMSO-d6) δ9.20 (d, J=6.6 Hz, 1H), 8.77-8.70 (m, 1H), 8.61-8.45 (m, 3H), 7.82 (dd, J=9.1, 6.3 Hz, 1H), 7.38 (dd, J=8.3, 2.1 Hz, 1H), 7.28 (d, J=8.7 Hz, 1H), 7.23-7.09 (m, 2H); MS (ES+) m/z 520.7 (M+1), 522.7 (M+1).

Workup

  1. customThe mixture was partitioned between ethyl acetate (100 mL) and water (20 mL)
  2. washThe organic phase was washed with brine (2×10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. stirringThe reaction mixture was stirred for 3 h at ambient temperature
  8. concentrationconcentrated in vacuo
  9. additionThe residue was suspended in a mixture of dichloromethane and methanol (1:1, 50 mL)
  10. filtrationfiltered through a pad of diatomaceous earth
  11. concentrationThe filtrate was concentrated in vacuo
  12. customthe residue that was triturated in ethyl acetate

Sources & evidence

ORD record
ord-2cd154837ac745fda10f758e85925b67
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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