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

HRID 1817007

Reaktionsgleichung

Reaktionsgleichung von HRID 1817007
[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-2c4123f28f064d5195da0cc65ba6f823
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598236B2

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