Fumaric Acid → (cis)-6-(3-Pyridinyl)-3,6-diazabicyclo[3.2.0]heptane fumarate

HRID 1642177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1642177
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:13][C@@H:12]3[C@H:8]2[CH2:9][NH:10][CH2:11]3)[CH:2]=1.[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18]>>[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:13][C@@H:12]3[C@H:8]2[CH2:9][NH:10][CH2:11]3)[CH:2]=1

Komponenten

3

Edukt 2

HCID 444972Fumaric AcidHCID 9855608(1R,5S)-6-(3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane

Produkt 1

HCID 23636030(cis)-6-(3-Pyridinyl)-3,6-diazabicyclo[3.2.0]heptane fumarate

Versuchsvorschrift

The product (100 mg, 0.57 mmol) of Example 52F was treated with fumaric acid according to the procedure of Example 40D. The title compound was obtained as white solid (120 mg, 73% yield). 1H NMR (MeOH-d4, 300 MHz) δ 3.18 (dd, J=12.6, 3.4 Hz, 1H), 3.35 (m, 1H), 3.46 (m, 1H), 3.75 (m, 3H), 4.04 (t, J=7.8 Hz, 1H), 4.90 (m, 1H), 6.58 (s, 2H), 7.04 (ddd, J=8.2, 2.7, 1.3 Hz, 1H), 7.27 (dd, J=8.2, 4.8 Hz, 1H), 7.87 (d, 2.7 Hz, 1H), 7.95 (dd, J=4.8, 1.1 Hz, 1H); m/z 176 (M+H)+; Anal. calculated for C11H14ClN3.1.25C4H4O4.0.3H2O: C, 55.31; H, 5.76. Found: C, 54.97; H, 5.47.

Quellen und Nachweise

ORD-Eintrag
ord-a939862640384a158ed28efe9c7bc3da
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119635B2

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