Methanol → HCID 56601581, compound

HRID 1619610Notes

Reaction equation

HRID 1619610 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]([C:48]([F:51])([F:50])[F:49])[CH:43]=3)=[C:32]([Cl:52])[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]([C:48]([F:51])([F:49])[F:50])[CH:43]=3)=[C:32]([Cl:52])[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 58042252HCID 58042252, compound

Product 1

HCID 56601581HCID 56601581, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-4-(2-chloro-5-(pyridazin-4-yl)-3′-(trifluoromethyl)biphenyl-4-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 53, 231 mg, 0.29 mmol) was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (1 mL) added. The resulting solution was stirred at room temperature for 18 hours. Methanol (2 mL) was added and the reaction was stirred for 10 minutes. The resulting mixture was evaporated and azeotroped with methanol (2×10 mL). The residue was partitioned between ethyl acetate (50 mL) and water (20 mL). The ethyl acetate was separated and dried over MgSO4 and evaporated. The residue was chromatographed on silica eluting with dichloromethane:methanol:acetic acid 100:0:0 to 95:5:0.5 in 1% stages of methanol. The column product was stirred in dichloromethane (10 mL) for 20 minutes, the solid filtered off, and stirred in dichloromethane (5 mL) at reflux for 10 minutes. The solid was filtered to give the title compound (45 mg, 25%) as a white solid.

Workup

  1. stirringthe reaction was stirred for 10 minutes
  2. customThe resulting mixture was evaporated
  3. customazeotroped with methanol (2×10 mL)
  4. customThe residue was partitioned between ethyl acetate (50 mL) and water (20 mL)
  5. customThe ethyl acetate was separated
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was chromatographed on silica eluting with dichloromethane:methanol:acetic acid 100:0:0 to 95:5:0.5 in 1% stages of methanol
  9. stirringThe column product was stirred in dichloromethane (10 mL) for 20 minutes
  10. filtrationthe solid filtered off
  11. stirringstirred in dichloromethane (5 mL)
  12. temperatureat reflux for 10 minutes
  13. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-75bb9948eaef4223b21739d655cec1a0
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

Loading…