Methanol → HCID 56601579, compound

HRID 1619608Notes

Reaction equation

HRID 1619608 reaction equation
[Cl:1][C:2]1[C:3]([O:29][C:30]2[C:35]([C:36]3[CH:41]=[CH:40][N:39]=[N:38][CH:37]=3)=[CH:34][C:33]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=3)=[C:32]([Cl:49])[CH:31]=2)=[CH:4][C:5]([F:28])=[C:6]([S:8]([N:11](CC2C=CC(OC)=CC=2OC)[C:12]2[S:13][CH:14]=[N:15][N:16]=2)(=[O:10])=[O:9])[CH:7]=1.FC(F)(F)C(O)=O.CO>ClCCl>[Cl:1][C:2]1[C:3]([O:29][C:30]2[C:35]([C:36]3[CH:41]=[CH:40][N:39]=[N:38][CH:37]=3)=[CH:34][C:33]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=3)=[C:32]([Cl:49])[CH:31]=2)=[CH:4][C:5]([F:28])=[C:6]([S:8]([NH:11][C:12]2[S:13][CH:14]=[N:15][N:16]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 58042338HCID 58042338, compound

Product 1

HCID 56601579HCID 56601579, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chloro-4-(2-chloro-3′-fluoro-5-(pyridazin-4-yl)biphenyl-4-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 66, 165 mg, 0.22 mmol) was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (1 mL) was added. The reaction was stirred at room temperature for 3 hours. Methanol (5 mL) was added to quench the reaction and the suspension stirred vigorously for 18 hours. The mixture was diluted with dichloromethane (5 mL) and the resulting precipitate was filtered through Celite™ and washed with dichloromethane (2×5 mL) and the filtrate concentrated in vacuo. The residue was dissolved in dichloromethane and methanol and passed through a short silica plug eluting with dichloromethane/methanol (98:2). The material obtained was further purified by silica gel column chromatography using (dichloromethane/methanol/acetic acid 97:3:0.5) to give the title compound (17 mg, 13%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. stirringthe suspension stirred vigorously for 18 hours
  4. filtrationthe resulting precipitate was filtered through Celite™
  5. washwashed with dichloromethane (2×5 mL)
  6. concentrationthe filtrate concentrated in vacuo
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washeluting with dichloromethane/methanol (98:2)
  9. customThe material obtained
  10. customwas further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40bb712fb13e4415b30048e4005497c6
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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