Triethylamine → (9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(trifluoromethyl)thiazol-4-yl)methanone

HRID 471024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471024
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(O)=O.[O:19]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][N:22]([C:30]([C:32]2[N:33]=[C:34]([C:37]([F:40])([F:39])[F:38])[S:35][CH:36]=2)=[O:31])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(#N)C>[OH:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:27]1[CH2:28][CH2:29][C:24]2([O:19][CH2:20][CH2:21][N:22]([C:30]([C:32]3[N:33]=[C:34]([C:37]([F:38])([F:39])[F:40])[S:35][CH:36]=3)=[O:31])[CH2:23]2)[CH2:25][CH2:26]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 866367511-Oxa-4,9-diazaspiro[5,5]undecan-4-yl(2-(trifluoromethyl)thiazol-4-yl)methanone trifluoroacetate

Produkt 1

HCID 57989285(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(trifluoromethyl)thiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

2-(3-(Bromomethyl)phenyl)ethanol (example 6, step a) (0.354 g) was added to a solution of 1-oxa-4,9-diazaspiro[5.5]undecan-4-yl(2-(trifluoromethyl)thiazol-4-yl)methanone trifluoroacetate (example 25, step a) (0.74 g) and triethylamine (0.689 mL) in acetonitrile (15 mL) and the mixture stirred at 20° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution, the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 1% triethylamine and 3% methanol in dichloromethane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.640 g.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1fe860fdfd634c2b9fc5ec183803ce2f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

Notizen zur Reaktion

Wird geladen…