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Cesium carbonate → tert-Butyl-3-chloro-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

HRID 536545
ノート
印刷プレビュー

反応式

HRID 536545 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:23]([O:27][C:28](=[O:38])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35]Br)=[C:31]([Cl:37])[CH:30]=1)([CH3:26])([CH3:25])[CH3:24]>CC(C)=O.O>[C:23]([O:27][C:28](=[O:38])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:11]2[C:10](=[O:13])[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12]2)=[C:31]([Cl:37])[CH:30]=1)([CH3:26])([CH3:24])[CH3:25]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 19936776Tert-butyl-4-(bromomethyl)-3-chlorobenzoateHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

生成物 1

HCID 58460119tert-Butyl-3-chloro-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

試薬・触媒・溶媒 2

HCID 180Acetone溶媒
HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

An amount of 1.00 g (4.22 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one (preparation as per WO 2007/134862 Example 36A) and 2.07 g (6.37 mmol) of caesium carbonate were suspended in 15 ml of acetone and admixed with 1.69 g (5.52 mmol) of tert-butyl-4-(bromomethyl)-3-chlorobenzoate (preparation as per WO 2003/000692, Example 4b). The mixture was stirred at 50° C. for 18 h. The suspension was diluted with water. It was extracted with twice 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. Purification by flash chromatography over silica gel with elution with cyclohexane/ethyl acetate (gradient 9:1→3:2) gave 1.41 g (53% of theory) of the target compound in a purity of 74%.

後処理

  1. extractionIt was extracted with twice 15 ml of ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customfreed from the solvent on a rotary evaporator
  4. customPurification by flash chromatography over silica gel
  5. washwith elution with cyclohexane/ethyl acetate (gradient 9:1→3:2)
  6. customgave 1.41 g (53% of theory) of the target compound in a purity of 74%

出典と根拠

ORDレコード
ord-fac12883d60941e3a9b356802188bf9d
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859601B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート