3-Aminophenol → 1-(3-(2-Fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea

HRID 1917727ノート

反応式

HRID 1917727 の反応式
[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[O:7][N:6]=1)([CH3:4])[CH3:3].[NH2:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1.CN(C1C=CC=CN=1)C>C1COCC1>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[O:19])[O:7][N:6]=1)([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 115683-AminophenolHCID 218852-DimethylaminopyridineHCID 66876626Phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate

生成物 1

HCID 668757701-(3-(2-Fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To THF (10 mL) was added phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate from the previous step (500 mg, 1.9 mmol), 3-aminophenol (207 mg, 1.9 mmol) and dimethylaminopyridine (60 mg, 0.5 mmol) and the mixture stirred overnight at room temperature. The mixture was concentrated in vacuo and purified by chromatography on silica gel (10-50% EtOAc/hexanes) to afford 1-(3-(2-fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea (390 mg, 1.4 mmol, 74%). LC-MS (ESI) m/z 280 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by chromatography on silica gel (10-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ae15f05d79d14012966f779a1b1a747b
出典データセット
uspto-grants-2013_12
特許番号
US08618289B2

反応ノート

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