HCID 68947475, compound → HCID 25100874, compound

HRID 1967707Notes

Reaction equation

HRID 1967707 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 preperative 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 preperative 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-364ca7c109e743cfaa27d1c61e0156f6
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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