3-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-2'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide → HCID 56601185, compound

HRID 1619600Notes

Reaction equation

HRID 1619600 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]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[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]=[CH:18][C:17]=2[C:22]([F:25])([F:23])[F:24])=[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 580422833-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-2'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 56601185HCID 56601185, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-2′-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 21, 400 mg, 0.55 mmol) was dissolved in a 4M solution of HCl in 1,4-dioxane (9 mL). The mixture was stirred at room temperature for 2 hours and then concentrated in vacuo. The residue was purified by silica gel column chromatography (0%-15% methanol in dichloromethane gradient elution), followed by trituration in tert-butylmethyl ether. The residue was purified further by a silica plug column (0%-20% methanol in dichloromethane) to afford the title compound (73 mg, 23%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (0%-15% methanol in dichloromethane gradient elution)
  3. customThe residue was purified further by a silica plug column (0%-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-249bcadcdce8459a833f9bd488786f35
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

Loading…