Triethylamine → (9-(3-Chloro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 471101ノート

反応式

HRID 471101 の反応式
C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH:15]([C:18]1[S:19][CH:20]=[C:21]([C:23]([N:25]2[CH2:30][C:29]3([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[O:28][CH2:27][CH2:26]2)=[O:24])[N:22]=1)([CH3:17])[CH3:16].Br[CH2:37][C:38]1[CH:39]=[C:40]([CH2:45][CH2:46][OH:47])[CH:41]=[C:42]([Cl:44])[CH:43]=1>C(#N)C.ClCCl>[Cl:44][C:42]1[CH:43]=[C:38]([CH:39]=[C:40]([CH2:45][CH2:46][OH:47])[CH:41]=1)[CH2:37][N:33]1[CH2:32][CH2:31][C:29]2([O:28][CH2:27][CH2:26][N:25]([C:23]([C:21]3[N:22]=[C:18]([CH:15]([CH3:17])[CH3:16])[S:19][CH:20]=3)=[O:24])[CH2:30]2)[CH2:35][CH2:34]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 579892922-(3-(Bromomethyl)-5-chlorophenyl)ethanolHCID 66964182(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

生成物 1

HCID 57989350(9-(3-Chloro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (0.18 mL) was added to a suspension of (2-isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 22, step b) (0.217 g) and 2-(3-(bromomethyl)-5-chlorophenyl)ethanol (example 52, step b) (0.160 g) in acetonitrile (5 mL) and the resulting solution was stirred at room temperature overnight. The solution was then purified by flash chromatography on silica eluted with 1:5:94 triethylamine:methanol:dichloromethane to afford a gum. The gum was dissolved in dichloromethane and the solution was washed three times with water, dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the subtitled compound as a pale yellow foam. Yield 0.254 g.

後処理

  1. customThe solution was then purified by flash chromatography on silica
  2. washeluted with 1:5:94 triethylamine
  3. custommethanol:dichloromethane to afford a gum
  4. washthe solution was washed three times with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8f7bfaec7dc849ad80fcdca304713fb6
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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