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5-(2-Aminopyridin-4-yloxy)-2,3-dihydro-1H-indole-1-carboxylic acid methylamide → N1-Methyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2215499
ノート
印刷プレビュー

反応式

HRID 2215499 の反応式
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>C(O)(=O)C.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4]
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

4

反応物 1

HCID 210548125-(2-Aminopyridin-4-yloxy)-2,3-dihydro-1H-indole-1-carboxylic acid methylamide

生成物 1

HCID 21949141N1-Methyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide収率 61%

試薬・触媒・溶媒 2

HCID 160554manganese(III) acetate dihydrate触媒2 回HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

5-(2-Aminopyridin-4-yloxy)-2,3-dihydro-1H-indole-1-carboxylic acid methylamide (40 mg, 0.14 mmol) was dissolved in acetic acid (0.9 ml), manganese (III) acetate (29 mg, 0.17 mmol) was added thereto and the reaction mixture was stirred at 70° C. for 3.5 hours. Manganese (III) acetate (29 mg, 0.17 mmol) was further added, and the reaction mixture was further stirred at 70° C. for 0.5 hours. After naturally cooled to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were suspended in diethyl ether:acetone=3:1, filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (24 mg, 0.085 mmol, 61%) as colorless crystals.

後処理

  1. stirringthe reaction mixture was further stirred at 70° C. for 0.5 hours
  2. temperatureAfter naturally cooled to room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationacetone=3:1, filtered off
  8. washwashed with diethyl ether
  9. customdried under aeration

出典と根拠

ORDレコード
ord-4b07983ee1fd4bac98c9723558b3773a
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109219B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート