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Methanol → 1-{4-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-3-(3-trifluoromethyl-phenyl)-urea

HRID 1446729
ノート
印刷プレビュー

反応式

HRID 1446729 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]4[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[F:37][C:38]([F:49])([F:48])[C:39]1[CH:40]=[C:41]([N:45]=[C:46]=[O:47])[CH:42]=[CH:43][CH:44]=1.CO>CS(C)=O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]4[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:46]([NH:45][C:41]5[CH:42]=[CH:43][CH:44]=[C:39]([C:38]([F:37])([F:48])[F:49])[CH:40]=5)=[O:47])=[CH:22][CH:21]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]
参加物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 887MethanolHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 81531DiisopropylethylamineHCID 685461074-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzylamine

生成物 1

HCID 578634611-{4-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-3-(3-trifluoromethyl-phenyl)-urea収率 66%

試薬・触媒・溶媒

1
HCID 679Dimethyl Sulfoxide溶媒

実験手順

Dissolve 4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzylamine (2.37 g, 6.28 mmol) and diisopropylethylamine (2.44 g, 3.28 mL, 18.84 mmol) in dimethylsulfoxide under a nitrogen environment at room temperature. Add 3-trifluoromethylphenylisocyanate (1.17 g, 6.28 mmol) and stir the mixture for 2.5 hours. Pour the reaction contents onto a Varian SCX column (50 g) prewashed with methanol. Wash the column with dichloromethane, 1:1 methanol/dichloromethane and methanol (150 mL each). Elute the title compound with 2 N NH3/methanol (300 mL). Concentrate the methanolic solution to dryness and chromatograph on silica using 0→3→5→10% methanol/dichloromethane over 4, 15 and 30 minutes, respectively. Dissolve the product in heated CHCl3 (65 mL), followed by treatment with hexanes (5 mL) and cooling. Dry the resulting precipitate in vacuo to yield the product (2.33 g, 66%). MS(ES), m/z 565 (M+1).

後処理

  1. additionPour
  2. customthe reaction contents onto a Varian SCX column (50 g)
  3. washWash the column with dichloromethane, 1:1 methanol/dichloromethane and methanol (150 mL each)
  4. washElute the title compound with 2 N NH3/methanol (300 mL)
  5. concentrationConcentrate the methanolic solution to dryness and chromatograph on silica using 0→3→5→10% methanol/dichloromethane over 4, 15 and 30 minutes
  6. dissolutionDissolve the product in heated CHCl3 (65 mL)
  7. temperaturecooling
  8. customDry the resulting precipitate in vacuo

出典と根拠

ORDレコード
ord-8dd589494a32418aabdd969f6e7aecaf
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07666879B2

反応ノート

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