Hydrochloric Acid → HCID 57786237、化合物

HRID 1628880ノート

反応式

HRID 1628880 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:23]=[O:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=3[CH3:22])[CH2:12][CH2:13][CH2:14][N:7]21.[F:25][C:26]([Si](C)(C)C)([F:28])[F:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([N:11]2[C:8]3=[N:9][C:10]4[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]([CH:23]([OH:24])[C:26]([F:28])([F:27])[F:25])[C:6]=4[N:7]3[CH2:14][CH2:13][CH2:12]2)=[C:16]([CH3:22])[CH:17]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilane2 回HCID 2724141Tetrabutylammonium Fluoride2 回HCID 57786225HCID 57786225、化合物

生成物 1

HCID 57786237HCID 57786237、化合物収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 9-chloro-1-(4-bromo-2-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (4.54 g, 11.2 mmol), trifluoromethyltrimethylsilane (4.97 mL, 33.7 mmol) in tetrahydrofuran (150 mL) was added tetrabutylammonium fluoride (1M solution in tetrahydrofuran 1.12 mL, 1.12 mmol), and the mixture was stirred at 0° C. for 15 min. To the reaction mixture was added tetrabutylammonium fluoride (1M solution in tetrahydrofuran 1.12 mL, 1.12 mmol), and the mixture was stirred at 0° C. for 15 min. To the reaction mixture was added trimethyl(trifluoromethyl)silane (4.97 mL, 33.7 mmol), and the mixture was stirred at 0° C. for 30 min. 1N hydrochloric acid (20 mL 20 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 10 min. The reaction mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-60% ethyl acetate/n-hexane gradient mixture. The desired fractions were concentrated in vacuo to give the title compound as a colorless powder (3.24 g, 6.83 mmol, 61%).

後処理

  1. stirringthe mixture was stirred at 0° C. for 15 min
  2. stirringthe mixture was stirred at 0° C. for 30 min
  3. stirringthe mixture was stirred at room temperature for 10 min
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-60% ethyl acetate/n-hexane gradient mixture
  10. concentrationThe desired fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-7123de28721c4cc3a6ea2f55b9ef8810
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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