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

HRID 471101노트

반응식

HRID 471101 반응식
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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8f7bfaec7dc849ad80fcdca304713fb6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

반응 노트

불러오는 중…