1H-Benzotriazole-1-methanol → 5-(2-(Methylamino)pyridin-4-yloxy)indole-1-carboxylic acid methylamide

HRID 2376899ノート

反応式

HRID 2376899 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)[CH:7]=[CH:6]1)=[O:4].N1(CO)C2C=CC=C[C:25]=2N=N1.[BH4-].[Na+]>C(O)C.CN(C)C=O>[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]([NH:21][CH3:25])[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4]

参加物

6

反応物 3

HCID 2241691H-Benzotriazole-1-methanolHCID 4311764Sodium borohydrideHCID 21949141N1-Methyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide

生成物 1

HCID 210548865-(2-(Methylamino)pyridin-4-yloxy)indole-1-carboxylic acid methylamide収率 20.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

N1-Methyl-5-(2-aminopyridin-4-yl)oxy-1H-1-indolecarboxamide (5.00 g, 17.7 mmol, Production example 5-1) was dissolved in ethanol (170 ml) and N,N-dimethylformamide (40 ml); 1H-benzotriazole-1-methanol (2.64 g, 17.7 mmol) was added thereto; and the reaction mixture was heated to reflux for 2 hours. After allowing to be cooled to room temperature, sodium borohydride (1.49 g, 35.4 mmol) was added to the reaction mixture; the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia BW-300, hexane-ethyl acetate-methanol system). The obtained crystals were suspended in acetone: diethyl ether =1:3, filtered off, washed with hexane, and dried to yield the title compound (1.05 g, 3.55 mmol, 20.1%) as pale yellow crystals.

後処理

  1. temperatureand the reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washand the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Fuji Silysia BW-300, hexane-ethyl acetate-methanol system)
  8. filtrationdiethyl ether =1:3, filtered off
  9. washwashed with hexane
  10. customdried

出典と根拠

ORDレコード
ord-afd3b4c437044e2483fa5196517ccebe
出典データセット
uspto-grants-2008_12
特許番号
US07468380B2

反応ノート

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