Hydrochloric Acid → HCID 86658249, 화합물

HRID 410538노트

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HRID 410538 반응식
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[C:7]([NH:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:8]=1.Cl[C:17]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=1.O>CS(C)=O>[Br:2][C:3]1[CH:4]=[C:5]([NH:15][C:17]2[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[CH:6]=[C:7]([NH:9][CH2:10][C:11]([F:13])([F:14])[F:12])[CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 58456392HCID 58456392, 화합물

생성물 1

HCID 86658249HCID 86658249, 화합물수율 50.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

Aqueous HCl (1.0 M, 1.5 mL, 1.5 mmol) was added to a stirred mixture of the product of Step 2 (0.80 g, 2.97 mmol) and 2-chloro-4-trifluoromethylpyrimidine (8.0 mL, 66.2 mmol) in DMSO and the mixture was stirred at 100° C. for 2 h. The mixture was cooled, water was added and the mixture was extracted with Et2O (3×). The combined organic fractions were washed with HCl, water, aqueous copper sulfate and brine, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (0-60% ethyl acetate in hexanes) to give 5-bromo-N-(2,2,2-trifluoroethyl)-N′-[4-(trifluoromethyl)-pyrimidin-2-yl]benzene-1,3-diamine (622 mg, 1.50 mmol, 50% yield) as a off-white solid. MS ESI: [M+H]+ m/z 416.9.

후처리

  1. temperatureThe mixture was cooled
  2. extractionthe mixture was extracted with Et2O (3×)
  3. washThe combined organic fractions were washed with HCl, water, aqueous copper sulfate and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (0-60% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-98d7e2a5ecf54386be9f3abc1d5cc38a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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