Ammonia → 1-[4-((1S,2S)-2-{[(2R)-2-methylpyrrolidin-1-yl]methyl}cyclopropyl)phenyl]azetidin-2-one

HRID 73316

Reaktionsgleichung

Reaktionsgleichung von HRID 73316
N1[NH:2][C:3](=[O:7])[CH:4]=[CH:5]C=1.Br[C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:17][C@@H:16]2[CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[CH3:24])=[CH:11][CH:10]=1.N>>[CH3:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[CH2:18][C@H:16]1[CH2:17][C@@H:15]1[C:12]1[CH:13]=[CH:14][C:9]([N:2]2[CH2:5][CH2:4][C:3]2=[O:7])=[CH:10][CH:11]=1

Komponenten

4

Edukt 3

HCID 222AmmoniaHCID 681533(2H)-PyridazinoneHCID 66796087(R)-1-(((1S,2S)-2-(4-bromophenyl)cyclopropyl)methyl)-2-methylpyrrolidine

Produkt 1

HCID 441973201-[4-((1S,2S)-2-{[(2R)-2-methylpyrrolidin-1-yl]methyl}cyclopropyl)phenyl]azetidin-2-one

Versuchsvorschrift

The title compound was prepared using the procedure described in Example 35B substituting azetidin-2-one for pyridazin-3(2H)-one and substituting the product from Example 35A for the product from Example 34F. 1H NMR (300 MHz, CD3OD) δ 0.98-1.04 (m, 1H), 1.08-1.15 (m, 1H), 1.34 (d, J=6 Hz, 3H), 1.35 (m, 1H), 1.59-1.72 (m, 1H), 1.94-2.04 (m, 3H), 2.18-2.29 (m, 1H), 2.75 (q, J=6 Hz, 1H), 2.98-3.07 (m, 1H), 3.08 (1, J=6 Hz, 2H), 3.16-3.26 (m, 1H), 3.32-3.36 (m, 1H), 3.52-3.62 (m, 1H), 3.65 (t, J=6 Hz, 2H), 7.11 (d, J=9 Hz, 2H), 7.30 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 299 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-57770974a94e4ea7bd970b30057edf74
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829041B2

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