Triethylamine → HCID 58827266, compound

HRID 448443Notes

Reaction equation

HRID 448443 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:22])[N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13].[N:23]1[CH:28]=[CH:27][N:26]=[CH:25][C:24]=1[C:29](Cl)=[O:30].C(N(CC)CC)C>C1COCC1>[O:21]=[C:15]1[CH:14]([N:7]2[C:6](=[O:22])[C:5]3[C:9](=[CH:10][CH:11]=[CH:12][C:4]=3[CH2:3][NH:2][C:29]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][N:23]=3)=[O:30])[C:8]2=[O:13])[CH2:19][CH2:18][C:17](=[O:20])[NH:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88279Pyrazinecarbonyl chlorideHCID 219885254-(aminomethyl)-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

Product 1

HCID 58827266HCID 58827266, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-aminomethyl-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione hydrochloride (0.63 g, 1.9 mmol), 2-pyrazinecarbonylchloride (0.25 g, 1.9 mmol) and triethylamine (0.61 g, 6.0 mmol) in THF (30 mL) was stirred at ambient temperature under nitrogen for 18 hours. The mixture was evaporated, and the residue was chromatographed using a methylene chloride-methanol gradient, eluting the product with 95:5 methylene chloride-methanol. This material dissolved in 4 mL acetonitrile, and this solution was poured into 50 mL of water, resulting in precipitation of the product, which was filtered, washed with additional water (20 mL), and dried, providing 0.46 g (61% yield): mp>260° C.; 1H NMR (DMSO-d6) δ 2.06-2.10 (m, 1H), 2.54-2.65 (m, 2H), 2.84-2.91 (m, 1H), 4.97 (d, J=6.3 Hz, 2H), 5.18 (dd, J=12.0 Hz, d=5.4 Hz, 1H), 7.69-7.83 (m, 3H), 8.29 (t, J=1.9 Hz, 1H), 8.91 (d, J=2.5 Hz, 1H), 9.21 (d, J=1.4 Hz, 1H), 9.61 (t, J=6.3 Hz, 1H), 11.15 (s, 1H); 13C NMR (DMSO-d6) δ 22.0, 30.9, 38.3, 48.9, 121.9, 127.2, 131.2, 131.6, 133.0, 134.7, 143.5, 143.6, 144.5, 147.7, 163.4, 167.0, 167.6, 169.8, 172.8; Anal. calcd for C19H15N5O5.0.5H2O: C, 56.71; H, 4.01; N, 17.41. Found: C, 56.64; H, 3.75; N, 17.28.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was chromatographed
  3. washeluting the product with 95:5 methylene chloride-methanol
  4. dissolutionThis material dissolved in 4 mL acetonitrile
  5. additionthis solution was poured into 50 mL of water
  6. customresulting in precipitation of the product, which
  7. filtrationwas filtered
  8. washwashed with additional water (20 mL)
  9. customdried
  10. customproviding 0.46 g (61% yield)

Sources & evidence

ORD record
ord-b51729c121e64bb8a62964bdf9538cbb
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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