Diisopropylethylamine → 1-(4-{[5-(3-Chlorophenyl)-6-methoxypyridin-3-yl]methyl}phenyl)-3-(oxetan-3-yl)urea

HRID 578837

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][C:17]3[CH:25]=[CH:24][C:20](C(O)=O)=[CH:19][CH:18]=3)[CH:11]=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.C([N:29]([CH2:33]C)C(C)C)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1.Cl.[O:53]1[CH2:56][CH:55]([NH2:57])[CH2:54]1>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][C:17]3[CH:25]=[CH:24][C:20]([NH:29][C:33]([NH:57][CH:55]4[CH2:56][O:53][CH2:54]4)=[O:42])=[CH:19][CH:18]=3)[CH:11]=[N:12][C:13]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 4-((5-(3-chlorophenyl)-6-methoxypyridin-3-yl)methyl)benzoic acid (Example 21, 90 mg, 0.25 mmol) in toluene (5 mL) was added N,N-diisopropylethylamine (33 mg, 0.25 mmol) and diphenylphosphoryl azide (77 mg, 0.28 mmol). The mixture was stirred at 80° C. for 30 minutes. The LCMS confirmed the disappearance of the starting acid. A solution of oxetan-3-amine hydrochloride (41.5 mg, 0.38 mmol), N,N-diisopropylethylamine (49 mg, 0.38 mmol) and DCM (2 mL) was added to the reaction mixture and stirred at room temperature for 2 h. The LCMS confirmed the presence of the product. All solvents were removed under reduced pressure. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound (50 mg, 46%). 1H NMR (400 MHz, CD3OD) δ 7.99 (d, J=2.3 Hz, 1H), 7.49 (d, J=2.3 Hz, 2H), 7.41-7.24 (m, 5H), 7.14 (d, J=8.6 Hz, 2H), 4.87 (br s, 3H), 4.55 (s, 2H), 3.91 (s, 3H), 3.90 (s, 2H). [M+H]=424.20.

Aufarbeitung

stirringstirred at room temperature for 2 h
customAll solvents were removed under reduced pressure
customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag: ord-090ae0a1a97948648335d4bfb4d8fe96
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09040692B2

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