Imidazole → [2-(5-Amino-6-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-methyl-carbamic acid tert-butyl ester

HRID 929131Notes

Reaction equation

HRID 929131 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15].[C:16]([O:20][C:21](=[O:27])[N:22]([CH2:24][CH2:25]N)[CH3:23])([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1>O1CCOCC1>[C:16]([O:20][C:21](=[O:27])[N:22]([CH2:24][CH2:25][N:6]1[C:5](=[O:15])[C:4]2[C:8](=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([NH2:1])[CH:3]=2)[C:7]1=[O:14])[CH3:23])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 2756424N-Boc-N-methylethylenediamineHCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 66793628[2-(5-Amino-6-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-methyl-carbamic acid tert-butyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-amino-6-nitro-isoindole-1,3-dione (2.07 g, 10 mmol), (2-Amino-ethyl)-methyl-carbamic acid tert-butyl ester (3.485 g, 20 mmol), imidazole (1.36 g, 20 mmol) in dioxane (30 mL) was sealed in a ChemGlass heavy wall pressure flask. After it was heated at 140° C. for 38 h, the reaction mixture was evaporated to dryness at 95° C. (the bath temperature) under reduced pressure. The chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (500:10:1) afforded the title compound (3.39 g, 93%). 1H NMR (CDCl3) δ 1.08 (s, 9H), 2.78 (s, 3H), 3.42 (m, 2H), 3.68 (m, 2H), 7.48 (s, 1H), 8.34 (s, 1H), 8.42 (br s, 2H, NH).

Workup

  1. customwas sealed in a ChemGlass heavy wall pressure flask
  2. customthe reaction mixture was evaporated to dryness at 95° C. (the bath temperature) under reduced pressure

Sources & evidence

ORD record
ord-f2e79a822cb64a5da66d712f1d826eed
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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