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Water → HCID 21310545, 화합물

HRID 583123
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HRID 583123 반응식
[H-].[Na+].[I-].C[S+](C)(C)=O.O=[C:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[N:22]=3)=[C:19]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:18]=[CH:17]2)[CH2:12][CH2:11]1.O.[CH2:37]1[CH2:41][O:40]CC1>CS(C)=O>[O:40]1[CH2:41][CH:37]1[CH:10]1[CH2:11][CH2:12][CH:13]([N:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[N:22]=3)=[C:19]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:18]=[CH:17]2)[CH2:14][CH2:15]1
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참가 물질

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반응물 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10090302HCID 10090302, 화합물

생성물 1

HCID 21310545HCID 21310545, 화합물수율 53%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

Added to a mixture of sodium hydride (0.05 g, 0.88 mmol) in DMSO (1 mL) was trimethyl sulfoxonium iodide (0.29 g, 1.3 mmol). After stirring the resultant mixture 1.5 h. (when gas evolution ceases), 1-(4-oxocyclohexyl)-4-(4-fluorophenyl)-5-[(2-methoxy)pyrimidin-4-yl]imidazole from example 1(j) (0.322 g, 0.88 mmol) suspended in dry THF (4 mL) was added and the mixture was stirred 4 h. The mixture was poured into H2O and extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated. The resulting residue was suspended in EtOAc/hexane (1:1) and filtered. The solid was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2) to afford the title compound as white crystals (0.18 g, 53% yield) 1H NMR (CDCl3): δ 8.35 (d, 1H), 7.85 (s, 1H), 7.43 (q, 2H), 7.02 (t, 2H), 6.80 (d, 1H), 4.86 (m, 1H), 4.09 (s, 3H), 2.76 (s, 2H), 226 (m, 2H), 2.20-2.02 (m, 4H), 1.43 (d, 2H).

후처리

  1. additionwas added
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customThe solid was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-023d925c6c3046ad99e777b80bff3782
출처 데이터셋
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05929076

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