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

HRID 393798Notes

Reaction equation

[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

Participants

Reactant 2

HCID 444972Fumaric Acid

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

Product 1

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

Procedure

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) δ3.18 (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.

Sources & evidence

ORD record: ord-3eacab04864c424aaa703a56809999b8
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809105B2

Reaction notes

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