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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
ノート
印刷プレビュー

反応式

HRID 2183880 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 2723949ThioacetamideHCID 101551885'-(7-Acetylimidazo[1,2-alpha]pyrimidin-3-yl)-2'-fluorobiphenyl-2-carbonitrileHCID 21124087Pyridiniumtribromide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2051d9ee8de04ca59ed2e54b227c71f6
出典データセット
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06900215B2

反応ノート

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