Ammonium Chloride → HCID 178509252, 화합물

HRID 46264노트

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HRID 46264 반응식
[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=2[C:40]2[C:41]([N+:51]([O-])=O)=[N:42][N:43](C3CCCCO3)[CH:44]=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.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:51][C:41]1[C:40]([C:31]2[CH:32]=[C:33]([C:36]([F:37])([F:39])[F:38])[CH:34]=[CH:35][C:30]=2[O:29][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([NH:11][C:12]3[S:13][CH:14]=[N:15][N:16]=3)(=[O:10])=[O:9])=[C:5]([F:28])[CH:4]=2)=[CH:44][NH:43][N:42]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 669058755-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-(trifluoromethyl)phenoxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

생성물 1

HCID 178509252HCID 178509252, 화합물

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

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온도
80 °C

실험 절차

To a solution of 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-{2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-(trifluoromethyl)phenoxy}-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 867, 3.20 g, 4.00 mmol) in ethanol (200 mL) was added saturated aqueous ammonium chloride solution (50 mL) and iron (5.66 g, 101 mmol). The reaction solution was heated at 80° C. for 15 minutes. The solution was cooled, filtered and adjusted to pH=9 with saturated aqueous sodium bicarbonate solution. The mixture was filtered and then concentrated to remove most of the ethanol. The resulting slurry was extracted with dichloromethane (3×). The organic extracts were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. This provided the aminopyrazole as a yellow foam. To this was added an HCl (g) saturated methanol solution (200 mL) and the mixture heated at 60° C. for two hours. The reaction solution was cooled, concentrated, and purified by automated flash column chromatography using a 0-10% methanol/dichloromethane gradient. Additional purification by prep HPLC provided the TFA salt. The resulting white solid was redissolved in a HCl (g) saturated methanol solution and concentrated (3×) in order to isolate the HCl salt of the title compound (1.20 g, 53%) as a white solid.

후처리

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customto remove most of the ethanol
  6. extractionThe resulting slurry was extracted with dichloromethane (3×)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a56b2fb34d9b4a5b801b4d1e1d9caa42
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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