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

HRID 2215574노트

반응식

HRID 2215574 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79a09a79ed054b66b7b22ac76a6da318
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109219B2

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