3-Aminopiperidine-2,6-dione hydrochloride → HCID 25015139, compound

HRID 1690468Notes

Reaction equation

HRID 1690468 reaction equation
[F:1][C:2]1[C:10]2[CH:9]=[C:8]([CH2:11][O:12][C:13]3[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([OH:18])=O)[C:14]=3[C:22](O)=[O:23])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:26][CH:27]1[CH2:33][CH2:32][C:31](=[O:34])[NH:30][C:28]1=[O:29]>N1C=CC=CC=1>[O:29]=[C:28]1[CH:27]([N:26]2[C:22](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][C:13]=3[O:12][CH2:11][C:8]3[S:7][C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:10]=4[CH:9]=3)[C:16]2=[O:18])[CH2:33][CH2:32][C:31](=[O:34])[NH:30]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 66906306HCID 66906306, compound

Product 1

HCID 25015139HCID 25015139, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(4-fluoro-benzo[b]thiophen-2-ylmethoxy)-phthalic acid (1.2 g, 3.4 mmol), alpha-amino-glutarimide hydrochloride (0.58 g, 3.6 mmol) in pyridine was refluxed overnight. The mixture was evaporated and the residue was purified by flash column chromatography (methanol/methylene chloride) to give 2-(2,6-dioxo-piperidin-3-yl)-4-(4-fluoro-benzo[b]thiophen-2-ylmethoxy)-isoindole-1,3-dione as a white solid (0.66 g, 44% yield); HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 60/40 CH3CN/0.1% H3PO4, 3.08 min (97.5%); mp, 264-266° C.; 1H NMR (DMSO-d6) δ 2.01-2.08 (m, 1H, CHH), 2.54-2.95 (m, 2H, CHHCH2), 5.11 (dd, J=6, 12 Hz, 1H, CH), 5.73 (s, 2H, CH2), 7.18-7.88 (m, 7H, Ar), 11.12 (s, 1H, NH); 13C NMR (DMSO-d6) δ21.98, 30.95, 48.82, 65.85, 109.57, 109.81, 116.04, 116.91, 118.02, 119.02, 119.07, 120.37, 125.98, 126.08, 127.39, 127.65, 133.38, 137.02, 140.81, 141.98, 142.06, 154.81, 155.10, 158.41, 165.17, 166.71, 169.91, 172.78. Anal Calcd For C22H15N2O5SF: C, 60.27; H, 3.45; N, 6.39; S, 7.31; F, 4.33. Found: C, 60.40; H, 3.26; N, 6.29; S, 7.24; F, 4.32.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash column chromatography (methanol/methylene chloride)

Sources & evidence

ORD record
ord-cdf7831e30ec4decbd9583aae66ae79c
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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