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p-Toluenesulfonic acid → 1-{[2-(Methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(3,3,3-trifluoropropyl)imidazolidin-2-one

HRID 1851713
ノート
印刷プレビュー

反応式

HRID 1851713 の反応式
[CH3:1][O:2][CH2:3][C:4]1[S:8][C:7]2=[N:9][C:10]([C:14]([F:17])([F:16])[F:15])=[C:11]([CH2:12]O)[N:6]2[N:5]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:29][C:30]([F:40])([F:39])[CH2:31][CH2:32][CH:33]1[CH2:37][NH:36][C:35](=[O:38])[NH:34]1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[S:8][C:7]2=[N:9][C:10]([C:14]([F:17])([F:16])[F:15])=[C:11]([CH2:12][N:36]3[CH2:37][CH:33]([CH2:32][CH2:31][C:30]([F:39])([F:40])[F:29])[NH:34][C:35]3=[O:38])[N:6]2[N:5]=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

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 70976689HCID 70976689、化合物HCID 86720187HCID 86720187、化合物

生成物 1

HCID 665716681-{[2-(Methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(3,3,3-trifluoropropyl)imidazolidin-2-one収率 64%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanol a3 (3.26 g, 0.122 mol, 1 eq) and p-toluenesulphonic acid (2.10 g, 0.122 mol, 1 eq) are successively added to a solution of 4-(3,3,3-trifluoropropyl)imidazolidin-2-one a10 (2.22 g, 0.122 mol, 1 eq) in toluene (450 ml). The mixture is heated at 110° C. overnight. The reaction is not complete and another portion of intermediate a10 (1 g, 5.49 mmol, 0.45 eq) is added. The mixture is heated at 110° C. overnight, then the solvent is evaporated under reduced pressure. Water is added to the residue, the mixture is extracted with CH2Cl2, the organic layer is dried over MgSO4, filtered and condensed under reduced pressure. The residue is purified by chromatography over silicagel (eluent: CH2Cl2/MeOH/NH4OH 98/2/0.2) to afford 336 mg of 1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(3,3,3-trifluoropropyl)imidazolidin-2-one 5 as a yellow oil.

後処理

  1. additionanother portion of intermediate a10 (1 g, 5.49 mmol, 0.45 eq) is added
  2. temperatureThe mixture is heated at 110° C. overnight
  3. customthe solvent is evaporated under reduced pressure
  4. additionWater is added to the residue
  5. extractionthe mixture is extracted with CH2Cl2
  6. dry with materialthe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. customcondensed under reduced pressure
  9. customThe residue is purified by chromatography over silicagel (eluent: CH2Cl2/MeOH/NH4OH 98/2/0.2)

出典と根拠

ORDレコード
ord-2e15e2b5319e40f59db3ff491547f2be
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08957218B2

反応ノート

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