HCID 58042271, compound → HCID 56601582, compound

HRID 1619611Notes

Reaction equation

HRID 1619611 reaction equation
[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([C:43]([F:46])([F:45])[F:44])[CH:37]=3)=[CH:32][C:31]=2[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=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>Cl.O1CCOCC1.CO>[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([C:43]([F:44])([F:45])[F:46])[CH:37]=3)=[CH:32][C:31]=2[C:47]2[CH:52]=[CH:51][N:50]=[N:49][CH:48]=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:9])=[O:10])[CH:7]=1

Participants

5

Reactant 1

HCID 58042271HCID 58042271, compound

Product 1

HCID 56601582HCID 56601582, compoundYield 68.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

5-Chloro-4-(4′-chloro-3-(pyridazin-4-yl)-3′-(trifluoromethyl)biphenyl-4-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 57, 135 mg, 0.17 mmol) was dissolved in a 4M solution of HCl in dioxane (5 mL), methanol (5 mL) added and the resulting mixture was stirred at 50° C. for 6 hours. The reaction mixture was evaporated and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate was separated, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica eluting with a gradient of dichloromethane:methanol:acetic acid 100:0:0 to 95:4:0.4 to give the title compound (75 mg, 68%) as a white solid.

Workup

  1. additionadded
  2. customThe reaction mixture was evaporated
  3. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. customThe ethyl acetate was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica eluting with a gradient of dichloromethane:methanol:acetic acid 100:0:0 to 95:4:0.4

Sources & evidence

ORD record
ord-5cb6e5ccd26c4208a7c481c6718cca83
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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