HCID 68947475, compound → HCID 25100874, compound

HRID 628645Notes

Reaction equation

HRID 628645 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1/[CH:13]=[CH:14]/[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][N:24]2C(=O)C3C(=CC=CC=3)C2=O)[CH:18]=[CH:19][CH:20]=1>CO>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1/[CH:13]=[CH:14]/[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][NH2:24])[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 68947475HCID 68947475, compound

Product 1

HCID 25100874HCID 25100874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-2-(3-(3-(2-(1-methoxynaphthalen-2-yl)vinyl)phenyl)propyl)isoindoline-1,3-dione was deprotected following the method used in Example 76 except that the reaction was conducted in MeOH at room temperature for 2 h. The reaction was concentrated under reduced pressure. The white solid was washed with diethyl ether and the decanted solution was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (1:10:89 NH4OH:MeOH:CH2Cl2) to give Example 92. Yield (0.020 g, 57%): 1H NMR (400 MHz, DMSO-d6) δ 8.07 (d, J=8.4 Hz, 1H), 7.91 (d, J=8.8 Hz, 2H), 7.71 (d, J=8.8 Hz, 1H), 7.46-7.57 (m, 5H), 7.38 (d, J=16.4 Hz, 1H), 7.31 (t, J=7.6 Hz, 1H), 7.13 (d, J=7.6 Hz, 1H), 3.91 (s, 3H), 2.62-2.66 (m, 2H), 2.57 (t, J=6.8 Hz, 2H), 1.64-1.72 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washThe white solid was washed with diethyl ether
  3. concentrationthe decanted solution was concentrated under reduced pressure
  4. customThe residue was purified by preparative thin layer chromatography on silica gel (1:10:89 NH4OH:MeOH:CH2Cl2)
  5. customto give Example 92
  6. customYield (0.020 g, 57%)

Sources & evidence

ORD record
ord-74fe45b458d440498c34c0fbc49ededf
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

Loading…