Piperidine → HCID 58312939, compound

HRID 1751190Notes

Reaction equation

Br[C:2]1[N:7]=[C:6](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CS(C)=O>[N:25]1([C:2]2[N:7]=[C:6](/[CH:8]=[C:9]3/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/3)[CH:5]=[CH:4][CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 110 °C

Procedure

A 2 dram round-bottomed vial was charged with (Z)-5-((6-bromopyridin-2-yl)methylene)thiazolidine-2,4-dione (60 mg, 0.210 mmol, 1 equiv.), DMSO (1 mL, 0.08 M), diisopropylethylamine (34 μL, 0.2 mmol, 1 equiv.), and piperidine (21 μL, 0.21 mmol, 1 equiv.), and the reaction was heated with shaking at 110° C. for 24 h. The solvent was removed under reduced pressure (Genvac HT-4) and the crude residue was purified using reverse phase HPLC (MS-triggered fraction collection) with an acetonitrile/water gradient and trifluoroacetic acid as a modifier. The pure fractions were then concentrated under reduced pressure (Genevac HT-4) to provide (Z)-5-((6-(piperidin-1-yl)pyridin-2-yl)methylene)thiazolidine-2,4-dione (7.9 mg, 60.9 mg theoretical, 12.9%). LC-MS m/z 290.1 (M+1).

Workup

temperaturethe reaction was heated
customThe solvent was removed under reduced pressure (Genvac HT-4)
customthe crude residue was purified
customphase HPLC (MS-triggered fraction collection) with an acetonitrile/water gradient and trifluoroacetic acid as a modifier
concentrationThe pure fractions were then concentrated under reduced pressure (Genevac HT-4)

Sources & evidence

ORD record: ord-5710d7ca84304bb6b0d85d85920448d2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09157077B2

Reaction notes

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