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Potassium Carbonate → 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{2-pyridazin-4-yl-4-[6-(trifluoromethyl)pyridin-3-yl]phenoxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619668
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HRID 1619668 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)[CH:10]=[CH:9][C:8]=2[OH:23])=[CH:3][N:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[C:32](F)=[CH:33][C:34]([F:57])=[C:35]([S:37]([N:40]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=2[O:55][CH3:56])[C:41]2[S:42][CH:43]=[N:44][N:45]=2)(=[O:39])=[O:38])[CH:36]=1>CS(C)=O>[Cl:30][C:31]1[C:32]([O:23][C:8]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[N:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)=[CH:12][C:7]=2[C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)=[CH:33][C:34]([F:57])=[C:35]([S:37]([N:40]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=2[O:55][CH3:56])[C:41]2[S:42][CH:43]=[N:44][N:45]=2)(=[O:38])=[O:39])[CH:36]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 136200884HCID 136200884, 화합물

생성물 1

HCID 580423105-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{2-pyridazin-4-yl-4-[6-(trifluoromethyl)pyridin-3-yl]phenoxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide수율 58.2%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

2-(Pyridazin-4-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)phenol (Preparation 59, 360 mg, 1.134 mmol) was dissolved in DMSO (6 mL) and potassium carbonate (313 mg, 2.27 mmol) was added followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 16, 524 mg, 1.134 mmol). The reaction was stirred at room temperature for 18 hours and then partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage (20% to 100% EtOAc in heptane over 20 CV) to give the title compound (501 mg, 58%) as yellow foam.

후처리

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by Biotage (20% to 100% EtOAc in heptane over 20 CV)

출처 및 근거

ORD 기록
ord-d2f7121394b54870b87b9eb8984f48df
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772293B2

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