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

HRID 471101Notes

Reaction equation

HRID 471101 reaction equation
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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8f7bfaec7dc849ad80fcdca304713fb6
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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