Isoindoline → HCID 76902036, compound

HRID 1507027Notes

Reaction equation

HRID 1507027 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH:19]4[CH2:21][O:20]4)[CH:12]=3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[CH2:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][NH:23]1>CO>[CH2:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][N:23]1[CH2:21][CH:19]([OH:20])[CH2:18][O:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:4]=[CH:3][N:2]([CH3:1])[C:6]=3[CH:7]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 86729445HCID 86729445, compound

Product 1

HCID 76902036HCID 76902036, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-6-(3-(oxiran-2-ylmethoxy)phenyl)-1H-benzo[d]imidazole (500 mg, 1.78 mmol) in MeOH (5 mL) was added isoindoline (213 mg, 1.78 mmol) at 25° C., and the mixture was heated to reflux and stirred for 16 h. The reaction mixture was cooled, concentrated and purified by preparative HPLC purification. (80 mg, yield 11%) MS (ESI+) e/z: 400.2 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 8.22 (s, 1H), 7.87 (s, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.41-7.19 (m, 7H), 6.97-6.95 (m, 1H), 4.16-4.04 (m, 7H), 3.89 (s, 3H), 3.04-2.87 (m, 2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. custompurified by preparative HPLC purification

Sources & evidence

ORD record
ord-8dacf3df31c4467b8ae3d2e82c31f1fd
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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