Triethylamine → Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoate

HRID 911869

Reaktionsgleichung

Reaktionsgleichung von HRID 911869
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[Br:11][C:12]1[CH:13]=[C:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]([NH:18][C:19]([NH2:21])=[S:20])=[N:16][CH:17]=1.C(N(CC)CC)C>C(O)C>[Br:11][C:12]1[CH:13]=[C:14]([O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]([NH:18][C:19]2[S:20][CH:2]=[C:3]([CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[N:21]=2)=[N:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9855825Methyl 5-bromo-4-oxopentanoateHCID 866314811-(5-Bromo-3-phenoxypyridin-2-yl)thiourea

Produkt 1

HCID 86631509Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-bromo-4-oxopentanoate (2.51 g, 12.0 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (3.00 g, 9.25 mmol), triethylamine (2.19 mL, 15.7 mmol), and ethanol (60 mL) was refluxed for 3 hours and then stirred at ambient temperature overnight. The solvent was removed to about one third original volume and partitioned between CH2Cl2 and water. The organics were concentrated and purified on silica gel eluting with 40% EtOAc/Hexanes to give the title compound (3.22 g, 80.1% yield).

Aufarbeitung

  1. temperaturewas refluxed for 3 hours
  2. customThe solvent was removed to about one third original volume
  3. custompartitioned between CH2Cl2 and water
  4. concentrationThe organics were concentrated
  5. custompurified on silica gel eluting with 40% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-16cb3420468b41fc98fb55df90cecb09
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022223B2

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