Diisopropylethylamine → (E)-2'-(methylamino)-5-((1-(pent-2-enoyl)azetidin-3-yl)amino)-[3,4'-bipyridin]-6(1H)-one

HRID 2283479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283479
Br.Br.[NH:3]1[CH2:6][CH:5]([NH:7][C:8]2[C:13](=[O:14])[NH:12][CH:11]=[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[CH:16]=3)[CH:9]=2)[CH2:4]1.[C:23](O)(=[O:28])/[CH:24]=[CH:25]/[CH2:26][CH3:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:22][NH:21][C:17]1[CH:16]=[C:15]([C:10]2[CH:9]=[C:8]([NH:7][CH:5]3[CH2:6][N:3]([C:23](=[O:28])/[CH:24]=[CH:25]/[CH2:26][CH3:27])[CH2:4]3)[C:13](=[O:14])[NH:12][CH:11]=2)[CH:20]=[CH:19][N:18]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 638122trans-2-Pentenoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1182509885-(azetidin-3-ylamino)-2'-(methylamino)-[3,4'-bipyridin]-6(1H)-one di-hydrobromide

Produkt 1

HCID 118251020(E)-2'-(methylamino)-5-((1-(pent-2-enoyl)azetidin-3-yl)amino)-[3,4'-bipyridin]-6(1H)-oneAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(azetidin-3-ylamino)-2′-(methylamino)-[3,4′-bipyridin]-6(1H)-one di-hydrobromide (Example 14, Step 4, 80 mg, 0.19 mmol), in DMF (1 mL) was added (E)-pent-2-enoic acid (28 mg 0.28 mmol), HATU (105 mg, 0.277 mmol), and DIPEA (120 mg, 0.923 mmol). The reaction mixture was stirred at RT under nitrogen for 16 h. The residue was purified by Prep. HPLC to afford (E)-2′-(methylamino)-5-((1-(pent-2-enoyl)azetidin-3-yl)amino)-[3,4′-bipyridin]-6(1H)-one (34 mg, 42%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 12.02 (s, 1H), 8.10 (d, J=5.3 Hz, 1H), 7.11 (d, J=2.1 Hz, 1H), 6.97 (dt, J=15.3, 6.4 Hz, 1H), 6.62 (dd, J=5.3, 1.6 Hz, 1H), 6.38 (d, J=1.8 Hz, 2H), 5.85 (dt, J=15.3, 1.7 Hz, 1H), 5.48 (d, J=6.6 Hz, 1H), 4.80 (d, J=5.5 Hz, 1H), 4.60 (t, J=7.9 Hz, 1H), 4.55-4.46 (m, 1H), 4.33 (dt, J=12.5, 6.3 Hz, 1H), 4.07 (m, 2H), 2.97 (d, J=4.9 Hz, 3H), 2.22 (m, 2H), 1.06 (t, J=7.4 Hz, 3H); MS (ES) m/z 354 (M+H).

Aufarbeitung

  1. customThe residue was purified by Prep

Quellen und Nachweise

ORD-Eintrag
ord-2f6e1fbff18942829efc91f4dda6b2da
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145393B2

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