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

HRID 871329ノート

反応式

HRID 871329 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-2b159d9fe51348ecb6e1096e215616f8
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

反応ノート

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