HCID 86709856, compound → HCID 86709855, compound

HRID 2277121Notes

Reaction equation

HRID 2277121 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:21][CH3:22])[C:14]=3[N+:18]([O-])=O)[C:9]2=[O:23])[CH2:6][CH2:5][C:4](=[O:24])[NH:3]1.[H][H]>[Pd].CN(C=O)C>[NH2:18][C:14]1[C:13]([O:21][CH3:22])=[CH:12][CH:11]=[C:10]2[C:15]=1[C:16](=[O:17])[N:8]([CH:7]1[CH2:6][CH2:5][C:4](=[O:24])[NH:3][C:2]1=[O:1])[C:9]2=[O:23]

Participants

5

Reactant 2

HCID 86709856HCID 86709856, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86709855HCID 86709855, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

In yet another embodiment, the process provided herein for preparing 4-amino-2-(2,6-dioxopiperidin-3-yl)-5-hydroxyisoindoline-1,3-dione, or an enantiomer or a mixture of enantiomers thereof; or a pharmaceutically acceptable salt, solvate, hydrate, or polymorph thereof; comprises the steps of (i) reducing 2-(2,6-dioxopiperidin-3-yl)-5-methoxy-4-nitroisoindoline-1,3-dione with hydrogen in the presence of (a) a catalyst, in one embodiment, Pd/C; in (b) a solvent, in one embodiment, DMF; to form 4-amino-2-(2,6-dioxopiperidin-3-yl)-5-methoxyisoindoline-1,3-dione; and (ii) reacting form 4-amino-2-(2,6-dioxopiperidin-3-yl)-5-methoxyisoindoline-1,3-dione with BBr3 to 4-amino-2-(2,6-dioxopiperidin-3-yl)-5-hydroxyisoindoline-1,3-dione.

Workup

  1. additionan enantiomer or a mixture of enantiomers

Sources & evidence

ORD record
ord-a9df61e9b3ac4916977da07760e834f8
Source dataset
uspto-grants-2015_09
Patent number
US09133161B2

Reaction notes

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