PyBroP → Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate

HRID 1896834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896834
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11](O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:44][CH2:45][C:46]([NH:48][CH:49]1[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50]1)=[O:47]>O1CCOCC1>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11]([NH:44][CH2:45][C:46]([NH:48][CH:49]2[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50]2)=[O:47])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1

Komponenten

5

Edukt 3

HCID 2733179PyBroPHCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylateHCID 1785161332,6-Bis(trifluoromethyl)quinolin-4(1H)-one

Produkt 1

HCID 86660461Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of commercially available 2,6-bis(trifluoromethyl)quinolin-4-ol (291 mg, 1.04 mmol) in dry dioxane (5 mL) was treated sequentially with TEA (0.36 mL, 2.58 mmol) and PyBrOP (586 mg, 1.26 mmol). After stirring 1 hour at room temperature under argon, a solution of tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (352, 1.54 mmol), prepared as described in Example 1, Step E in dry dioxane (5 mL) was introduced and the reaction mixture was stirred overnight at room temperature. After concentration in vacuo, the residue was purified by flash chromatography (silica gel, 0-5% MeOH/ethyl acetate) to afford the product.

Aufarbeitung

  1. additionwas introduced
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, 0-5% MeOH/ethyl acetate)
  5. customto afford the product

Quellen und Nachweise

ORD-Eintrag
ord-eb44cbf949534acbac30b55cb8526b6e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518969B2

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