HCID 67044585, compound → HCID 67044819, compound

HRID 2367109Notes

Reaction equation

HRID 2367109 reaction equation
[CH3:1][C:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([OH:29])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[N:13]2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:8][C:7]=1[N+:30]([O-])=O)([CH3:4])[CH3:3]>[Pd]>[NH2:30][C:7]1[CH:8]=[C:9]([C:12]2([OH:29])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[N:13]2[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:10]=[CH:11][C:6]=1[NH:5][C:2]([CH3:4])([CH3:3])[CH3:1]

Participants

3

Reactant 1

HCID 67044585HCID 67044585, compound

Product 1

HCID 67044819HCID 67044819, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 3-{4-[(1,1-dimethylethyl)amino]-3-nitrophenyl}-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (1.8 mg, 4.17 mmol) in a mixture of terahydrofuran-ethyl acetate (1:1, 20 mL) was hydrogenated over 10% Pd—C (50 mg) at 40 psi for 18 h. The catalyst removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford 3-{3-amino-4-[(1,1-dimethylethyl)amino]phenyl}-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (950 mg, 57%). MS (EI) for C25H27N3O2: 402 (MH+).

Workup

  1. customThe catalyst removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-1aa7cb8b67e549f6b30f7c6d04bd3d9c
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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