Hydrochloric Acid → HCID 86658249、化合物

HRID 410538ノート

反応式

HRID 410538 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 58456392HCID 58456392、化合物

生成物 1

HCID 86658249HCID 86658249、化合物収率 50.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-98d7e2a5ecf54386be9f3abc1d5cc38a
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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