Methanol → 5-Chloro-4-[(6-chloro-4'-fluoro-4-pyridazin-4-ylbiphenyl-3-yl)oxy]-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619617노트

반응식

HRID 1619617 반응식
[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:31]=[C:32]([C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[C:33]([Cl:42])=[CH:34][C:35]=2[C:36]2[CH:41]=[CH:40][N:39]=[N:38][CH:37]=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.CO>Cl.O1CCOCC1>[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:31]=[C:32]([C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[C:33]([Cl:42])=[CH:34][C:35]=2[C:36]2[CH:41]=[CH:40][N:39]=[N:38][CH:37]=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

참가 물질

5

반응물 2

HCID 887MethanolHCID 580422795-Chloro-4-(6-chloro-4'-fluoro-4-(pyridazin-4-yl)biphenyl-3-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

생성물 1

HCID 566019835-Chloro-4-[(6-chloro-4'-fluoro-4-pyridazin-4-ylbiphenyl-3-yl)oxy]-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide수율 60%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

5-Chloro-4-(6-chloro-4′-fluoro-4-(pyridazin-4-yl)biphenyl-3-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 101, 100 mg, 0.13 mmol) was dissolved in a 4M solution of HCl in dioxane (10 mL). The reaction mixture was stirred for 18 hours at room temperature. Methanol (50 mL) was added to the reaction mixture and the suspension was concentrated in vacuo. The crude residue was purified by reverse phase semi preparative HPLC (solvent A: 0.05% formic acid in acetonitrile, solvent B: 0.05% formic acid in water; flow rate: 12.5 ml/min; gradient: 0 min 10% A, 2.5 min 10% A, 32.5 min 95% A, 37.5 min 95% A then return to initial conditions) to afford the title compound (46 mg, 60%) as a solid.

후처리

  1. concentrationthe suspension was concentrated in vacuo
  2. customThe crude residue was purified by reverse phase semi preparative HPLC (solvent A
  3. custom0 min 10% A, 2.5 min 10% A, 32.5 min 95% A, 37.5 min 95% A

출처 및 근거

ORD 기록
ord-392c3a6992e540e099b4921346626338
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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