(Trifluoromethyl)trimethylsilane → HCID 89934088, 화합물

HRID 921900

반응식

HRID 921900 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]([Si](C)(C)C)([F:22])[F:21].[Cl:27][C:28]1[C:33]([CH:34]=[O:35])=[CH:32][C:31]([C:36]#[N:37])=[CH:30][C:29]=1[NH:38][C:39]1[N:44]=[C:43]([NH:45][CH:46]2[CH2:48][CH2:47]2)[C:42]2=[N:49][CH:50]=[C:51]([C:52]#[N:53])[N:41]2[N:40]=1>C1COCC1>[Cl:27][C:28]1[C:33]([CH:34]([OH:35])[C:20]([F:22])([F:21])[F:19])=[CH:32][C:31]([C:36]#[N:37])=[CH:30][C:29]=1[NH:38][C:39]1[N:44]=[C:43]([NH:45][CH:46]2[CH2:48][CH2:47]2)[C:42]2=[N:49][CH:50]=[C:51]([C:52]#[N:53])[N:41]2[N:40]=1

참가 물질

5

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 867086482-((2-Chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

생성물 1

HCID 89934088HCID 89934088, 화합물수율 17.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

TBAF (1 M in THF, 0.026 mL, 0.026 mmol) was added to a suspension of (trifluoromethyl)trimethylsilane (2 M solution in THF, 0.079 mL, 0.16 mmol) and 2-((2-chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (20 mg, 0.053 mmol) in dry THF (1 mL) under nitrogen in an ice bath. The bath was removed and the reaction was left stirring at room temperature overnight. Aqueous 1 N HCl was added and the reaction was left stirring for 20 min. This was neutralized with 1.3 N potassium phosphate buffer and extracted three times with EtOAc. The organic extracts were washed with brine and dried with sodium sulfate. Radial silica gel chromatography eluting with DCM containing 0 to 15% EtOAc afforded the title compound (4.1 mg) as oil.

후처리

  1. customThe bath was removed
  2. waitthe reaction was left
  3. additionAqueous 1 N HCl was added
  4. waitthe reaction was left
  5. stirringstirring for 20 min
  6. extractionextracted three times with EtOAc
  7. washThe organic extracts were washed with brine
  8. dry with materialdried with sodium sulfate
  9. washRadial silica gel chromatography eluting with DCM containing 0 to 15% EtOAc

출처 및 근거

ORD 기록
ord-b23867537013472ebed78883b6eab118
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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