Triethylamine → 4-(6-Methoxy-[1,5]naphthyridin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

HRID 456581

Reaktionsgleichung

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:51][O:52][C:53]1[N:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[N:59]=[CH:58][CH:57]=[C:56]2[NH2:63]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17](=[O:19])[NH:63][C:56]2[C:55]3[C:60](=[CH:61][CH:62]=[C:53]([O:52][CH3:51])[N:54]=3)[N:59]=[CH:58][CH:57]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A solution of acid (d) (7.9 g, 30 mmol) and triethylamine (4.2 ml, 3.03 g, 30 mmol) in N,N-dimethylformamide (50 ml) was treated with [O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate] (HATU) (9.5 g, 25 mmol). After 0.25 hours, amine (c) (3.5 g, 20 mmol) was added and the mixture heated at 50° C. overnight. Evaporation afforded an oil which was partitioned between ethyl acetate and dilute brine. Drying and evaporation afforded an oil (10 g) which was chromatographed on silica eluting with a 0–5% methanol in ethyl acetate gradient, affording an oil (6.0 g, 80%).

Aufarbeitung

customEvaporation
customafforded an oil which
customwas partitioned between ethyl acetate and dilute brine
customDrying
customevaporation

Quellen und Nachweise

ORD-Eintrag: ord-6a7f9a51ee624bff981dc1f03edc5955
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07186730B2

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