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Diethyl Ether → 2'-Fluoro-5'-[7-(2-methylthiazol-5-yl)imidazo[1,2-alpha]pyrimidin-3-yl]biphenyl-2-carbonitrile

HRID 2183880
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HRID 2183880 반응식
[C:1]([C:4]1[CH:9]=[CH:8][N:7]2[C:10]([C:13]3[CH:14]=[CH:15][C:16]([F:27])=[C:17]([C:19]4[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:18]=3)=[CH:11][N:12]=[C:6]2[N:5]=1)(=O)[CH3:2].[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:49]([NH2:52])(=[S:51])[CH3:50].C(OCC)C>C(Cl)(Cl)Cl>[F:27][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[N:7]3[CH:8]=[CH:9][C:4]([C:1]4[S:51][C:49]([CH3:50])=[N:52][CH:2]=4)=[N:5][C:6]3=[N:12][CH:11]=2)=[CH:18][C:17]=1[C:19]1[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=1
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HCID 3283Diethyl EtherHCID 2723949ThioacetamideHCID 101551885'-(7-Acetylimidazo[1,2-alpha]pyrimidin-3-yl)-2'-fluorobiphenyl-2-carbonitrileHCID 21124087Pyridiniumtribromide

생성물 1

HCID 101585372'-Fluoro-5'-[7-(2-methylthiazol-5-yl)imidazo[1,2-alpha]pyrimidin-3-yl]biphenyl-2-carbonitrile수율 11%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
50 °C

실험 절차

5′-(7-Acetylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile (80 mg, 0.22 mmol) and pyridinium tribromide (110 mg, 0.34 mmol) in chloroform (5 ml) was stirred at 50° C. for 3 h. Thioacetamide (33 mg, 0.44 mmol) was then added and the reaction stirred at 50° C. for 16 h. The resulting mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was purified by preparative thin-layer chromatography eluting with dichloromethane containing 5% methanol and 1% conc. ammonia to give a foam. Trituration with diethyl ether afforded 2′-fluoro-5′-[7-(2-methylthiazol-5-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile as a yellow solid (10 mg, 11%): δH (400 MHz, DMSO) 2.75 (3H, s), 7.56-7.68 (5H, m), 7.81-7.92 (3H, m), 7.98-8.05 (2H, m), 8.40 (1H, s), 9.12 (1H, s); m/z (ES+) 412 (M++H).

후처리

  1. customThe resulting mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate solution
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by preparative thin-layer chromatography
  7. washeluting with dichloromethane containing 5% methanol and 1% conc. ammonia
  8. customto give a foam

출처 및 근거

ORD 기록
ord-2051d9ee8de04ca59ed2e54b227c71f6
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06900215B2

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