3-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-3'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide → HCID 56600579, compound

HRID 1619585Notes

Reaction equation

HRID 1619585 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:32]([N:35](CC2C=CC(OC)=CC=2OC)[C:36]2[S:40][N:39]=[CH:38][N:37]=2)(=[O:34])=[O:33])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[CH:12][C:11]=1[C:26]1[CH:31]=[CH:30][N:29]=[N:28][CH:27]=1)#[N:2]>Cl.O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([S:32]([NH:35][C:36]2[S:40][N:39]=[CH:38][N:37]=2)(=[O:33])=[O:34])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)=[CH:12][C:11]=1[C:26]1[CH:31]=[CH:30][N:29]=[N:28][CH:27]=1)#[N:2]

Participants

4

Reactant 1

HCID 580422893-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-3'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 56600579HCID 56600579, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-3′-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 20, 386 mg, 0.52 mmol) was dissolved in a 4M solution of hydrogen chloride in 1,4-dioxane (13 mL) and stirred at room temperature for 18 hours. The reaction was concentrated in vacuo and purified using silica gel column chromatography (1% acetic acid in dichloromethane to 10% methanol and 1% acetic acid in dichloromethane gradient elution) followed by a second purification using silica gel column chromatography (0%-15% methanol in dichloromethane gradient elution) to afford the title compound (76 mg, 25%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified
  3. washsilica gel column chromatography (1% acetic acid in dichloromethane to 10% methanol and 1% acetic acid in dichloromethane gradient elution)
  4. customfollowed by a second purification
  5. washsilica gel column chromatography (0%-15% methanol in dichloromethane gradient elution)

Sources & evidence

ORD record
ord-620667272a504a9ca809b8df791b93c4
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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