Phosgene → 3-Benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione

HRID 2270235ノート

反応式

HRID 2270235 の反応式
[CH2:1]([O:8][NH:9][C:10](=[O:23])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([Cl:18])=[CH:13][C:12]=1[NH:19][CH:20]1[CH2:22][CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](Cl)(Cl)=[O:25]>O1CCOCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][N:9]1[C:10](=[O:23])[C:11]2[C:12](=[CH:13][C:14]([Cl:18])=[C:15]([F:17])[CH:16]=2)[N:19]([CH:20]2[CH2:21][CH2:22]2)[C:24]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 6371PhosgeneHCID 22632989N-Benzyloxy-4-chloro-2-cyclopropylamino-5-fluoro-benzamide

生成物 1

HCID 226328893-Benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione収率 46.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of N-benzyloxy-4-chloro-2-cyclopropylamino-5-fluoro-benzamide (Example D-3, 3.00 g, 8.96 mmol) in 1,4-dioxane (50 mL) was reacted with a 20% solution of phosgene (7.00 mL, 9.86 mmol) in toluene in a sealed tube. The mixture was heated to reflux for 24 hours, then cooled and quenched with H2O. The mixture was extracted three times with ethyl acetate, the organic layers combined, dried with sodium sulfate, and concentrated. The residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 1.5 g of the title compound as a solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperaturecooled
  4. customquenched with H2O
  5. extractionThe mixture was extracted three times with ethyl acetate
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-6f75bdf9195f4c478c4436a1a2f00b79
出典データセット
uspto-grants-2001_12
特許番号
US06331538B1

反応ノート

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