Methylamine → HCID 68701570、化合物

HRID 62006ノート

反応式

HRID 62006 の反応式
[CH3:1][NH2:2].O=[C:4]([C:11]1[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:34][C:35]1[CH:36]=[C:37]([C:52](=O)[CH2:53]Br)[CH:38]=[C:39]([N+:49]([O-:51])=[O:50])[C:40]=1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)C.C(O)(=O)C.CN(C)C=O>[CH2:27]([O:34][C:35]1[CH:36]=[C:37]([C:52]2[N:2]([CH3:1])[C:4]([C:11]3[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][CH:14]=[CH:15][CH:16]=3)=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:53]=2)[CH:38]=[C:39]([N+:49]([O-:51])=[O:50])[C:40]=1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

8

反応物 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 68702337HCID 68702337、化合物HCID 714457901-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2-bromoethan-1-one

生成物 1

HCID 68701570HCID 68701570、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of methylamine (0.63 mL, 33% EtOH solution, 5 mmol) in a mixture of ethanol (25 mL) and acetic acid (0.5 mL) at room temperature was added ethyl 3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoate (1.305 g, 5 mmol). The reaction mixture was heated at reflux for two hours whereupon the solvent was removed by evaporation under vacuum. To a solution of the crude product in dimethylformamide (25 mL) was added potassium carbonate (2.07 g, 15 mmol) in one portion followed by 1-(3,4-bis-benzyloxy-5-nitrophenyl)-2-bromo-ethanone (2.51 g, 5.50 mmol) and the mixture was then stirred at 100° C. Once no starting material was detectable, the reaction mixture was allowed to cool to room temperature and poured onto ice-cold 1 N aqueous hydrochloric acid (100 mL). The resulting precipitate was filtered off, washed with water and dried. The residue was chromatographed over silica gel. Homogeneous fractions were pooled and evaporated to give ethyl 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate, 2.492 g (79%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for two hours whereupon the solvent
  3. customwas removed by evaporation under vacuum
  4. temperatureto cool to room temperature
  5. additionpoured onto ice-cold 1 N aqueous hydrochloric acid (100 mL)
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customThe residue was chromatographed over silica gel
  10. customevaporated

出典と根拠

ORDレコード
ord-4bbcba62b55541e6a17091b2f8a8fad4
出典データセット
uspto-grants-2016_09
特許番号
US09446012B2

反応ノート

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