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

反応式

[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

参加物

反応物 2

HCID 444972Fumaric Acid

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

生成物 1

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

実験手順

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.

出典と根拠

ORDレコード: ord-2c4123f28f064d5195da0cc65ba6f823
出典データセット: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07598236B2

反応ノート

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