O-Phenylenediamine → HCID 49803415, compound

HRID 1020395Notes

Reaction equation

HRID 1020395 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1)[C:6]2=[O:15].[C:26]1([NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:33][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:17]([CH2:16][N:5]2[CH2:4][C:3]3[C:7](=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:2]=3[Br:1])[C:6]2=[O:15])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66688686HCID 66688686, compound

Product 1

HCID 49803415HCID 49803415, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-((4-Bromo-5,6-dimethoxy-1-oxoisoindolin-2-yl)methyl)benzoic acid (380 mg, 0.92 mmol) in the step 3, 1,2-phenylene diamine (199 mg, 1.84 mmol, 2 equiv.), and BOP (610 mg, 1.38 mmol, 1.5 equiv.) were dissolved in DMF (4 mL). Triethylamine (0.25 mL, 1.8 mmol, 2 equiv.) was added thereto, and stirred at room temperature for 1 night. The reaction proceeded until no starting material is detectable by TLC. The resulting mixture thus obtained was distilled under a reduced pressure to remove DMF. The resulting material was dissolved in methylene chloride and washed with saturated sodium bicarbonate solution. The isolated organic layer was collected, dried over anhydrous MgSO4, and distilled under a reduced pressure to remove solvent. The resulting residue was subjected to a silica gel column chromatography (EtOAc/hexane=9:1) to obtain the title compound (135 mg, 29%).

Workup

  1. customThe resulting mixture thus obtained
  2. distillationwas distilled under a reduced pressure
  3. customto remove DMF
  4. dissolutionThe resulting material was dissolved in methylene chloride
  5. washwashed with saturated sodium bicarbonate solution
  6. customThe isolated organic layer was collected
  7. dry with materialdried over anhydrous MgSO4
  8. distillationdistilled under a reduced pressure
  9. customto remove solvent

Sources & evidence

ORD record
ord-3066de29ddea4694b0c32ad0cba84042
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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