Sodium Iodide → HCID 86765192, compound

HRID 1056930Notes

Reaction equation

HRID 1056930 reaction equation
[I-].[Na+].Br[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[C:14](=[O:20])[N:13]([CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[C:12]1[C:30]3[CH:31]=[C:32]4[O:40][CH2:39][O:38][C:33]4=[CH:34][C:35]=3[C:36](=[O:37])[C:11]2=1.[CH2:41]([NH2:43])[CH3:42]>O1CCOCC1.C(Cl)(Cl)Cl>[CH2:41]([NH:43][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[C:14](=[O:20])[N:13]([CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[C:12]1[C:30]3[CH:31]=[C:32]4[O:40][CH2:39][O:38][C:33]4=[CH:34][C:35]=3[C:36](=[O:37])[C:11]2=1)[CH3:42]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6341EthylamineHCID 118453389HCID 118453389, compound

Product 1

HCID 86765192HCID 86765192, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium iodide (0.060 g, 0.408 mmol) and compound 19 (0.020 g, 0.034 mmol) were diluted with dioxane (8 mL), and ethylamine (0.020 mL, 0.408 mmol, 70 wt. % solution in water) was added dropwise. The mixture was stirred at reflux for 26 h. The mixture was diluted to a volume of 200 mL with CHCl3, washed with H2O (2×50 mL) and saturated aq NaCl (50 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography (SiO2, ˜40 g), eluting with a gradient of 0.5% MeOH in CHCl3, to yield the product 24 as a solid (0.009 g, 46%): mp 187-188° C. (dec). IR (film) 1648, 1553, 1392, 1254, 1116, 1033, 785 cm−1; 1H NMR (CDCl3) δ 7.53 (s, 1H), 7.24 (s, 1H), 6.90 (s, 1H), 6.60 (s, 1H), 5.89 (s, 2H), 4.06 (s, 2H), 3.85 (s, 6H), 3.72 (s, 3H), 3.49-3.38 (m, 4H), 3.19-3.12 (m, 9H), 2.25-2.19 (m, 4H); ESIMS m/z 550 (MH+); HRESIMS m/z 550.2553 (MH+), calcd for C30H36N3O7 550.2553; HPLC purity: 98.36% (C-18 reverse phase, MeOH—H2O, 80:20).

Workup

  1. additionwas added dropwise
  2. temperatureat reflux for 26 h
  3. washwashed with H2O (2×50 mL) and saturated aq NaCl (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (SiO2, ˜40 g)
  7. washeluting with a gradient of 0.5% MeOH in CHCl3

Sources & evidence

ORD record
ord-a994f17de19b4a6e88d91f669b3444f2
Source dataset
uspto-grants-2016_07
Patent number
US09399660B2

Reaction notes

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