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

HRID 471101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471101
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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8f7bfaec7dc849ad80fcdca304713fb6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

Notizen zur Reaktion

Wird geladen…