Triethylamine → 3-(3-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)propoxy)benzaldehyde

HRID 471221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471221
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=1)(=O)=O.FC(F)(F)C(O)=O.[CH3:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([N:33]2[CH2:38][C:37]3([CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[O:36][CH2:35][CH2:34]2)=[O:32])[N:30]=1.C(N(CC)CC)C>C(#N)C>[CH3:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([N:33]2[CH2:38][C:37]3([CH2:43][CH2:42][N:41]([CH2:6][CH2:7][CH2:8][O:9][C:10]4[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=4)[CH:16]=[O:17])[CH2:40][CH2:39]3)[O:36][CH2:35][CH2:34]2)=[O:32])[N:30]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 579891193-(3-Formylphenoxy)propyl methanesulfonateHCID 66964121(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

Produkt 1

HCID 579889423-(3-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)propoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 3-(3-formylphenoxy)propyl methanesulfonate (example 95, step a) (0.209 g) and (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 4, step h) (0.32 g) and triethylamine (0.282 mL) in acetonitrile (10 mL) were heated at 65° C. for 18 hours. The solvent was evaporated off under reduced pressure and the residue partitioned between ethyl acetate and brine. 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 2% methanol and 1% triethylamine in dichloromethane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.157 g.

Aufarbeitung

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  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-7c40511e2d324a6598805b0669adcaa4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

Notizen zur Reaktion

Wird geladen…