Hydrochloric Acid → HCID 57786237, 화합물

HRID 1399234노트

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HRID 1399234 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilane2회HCID 2724141Tetrabutylammonium Fluoride2회HCID 57786225HCID 57786225, 화합물

생성물 1

HCID 57786237HCID 57786237, 화합물수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8c780d15de8546c8a49d1c612cb36962
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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