HCID 68941765, compound → HCID 25100719, compound

HRID 628644Notes

Reaction equation

HRID 628644 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH:11]=[CH:12][CH:13]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][NH2:17])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 68941765HCID 68941765, compound

Product 1

HCID 25100719HCID 25100719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-2-(3-(3-(3-Methoxystyryl)phenyl)propyl)isoindoline-1,3-dione was deprotected following the method used in Example 90 except that the reaction mixture was stirred overnight in methanol. Purification by preparative thin layer chromatography on silica gel gave Example 97. Yield (0.010 g, 16%): 1H NMR (400 MHz, DMSO-d6) δ 7.42 (s, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.25-7.29 (m, 2H), 7.21 (d, J=4.0 Hz, 2H), 7.15-7.16 (m, 2H), 7.09 (d, J=7.2 Hz, 1H), 6.82-6.83 (m, 1H), 3.77 (s, 3H), 2.53-2.63 (m, 4H), 1.65-1.72 (m, 2H).

Workup

  1. customPurification by preparative thin layer chromatography on silica gel
  2. customgave Example 97
  3. customYield (0.010 g, 16%)

Sources & evidence

ORD record
ord-1cf7d2a34f8a462f8a89fca0c45e5e8d
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

Loading…