Hydrochloric Acid → HCID 59762125, compound

HRID 929134Notes

Reaction equation

HRID 929134 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].Cl.[CH3:17][N:18]([CH3:23])[CH:19]([CH3:22])[CH2:20]N.N1C=CN=C1.CCN(CC)CC>O1CCOCC1>[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])[N:6]([CH2:20][CH:19]([N:18]([CH3:23])[CH3:17])[CH3:22])[C:5]2=[O:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 8471TriethylamineHCID 892171,2-Propanediamine, N2,N2-dimethyl-HCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59762125HCID 59762125, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-amino-6-nitro-isoindole-1,3-dione (1.66 g, 8.0 mmol), HCl salt of 2-dimethylamino-propylamine (5.5 g, crude, <30 mmol), imidazole (1.36 g, 20 mmol) and Et3N (8.4 mL, 6.07 g, 60 mmol) in dioxane (80 mL) was sealed in a ChemGlass heavy wall pressure flask. After it was heated at 130° C. for 69 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 (240:10:1) afforded the title compound (360 mg, 15%). 1H NMR (DMSO-d6) δ 0.88 (d, J=6 Hz, 3H, CH3), 2.13 (s, 6H, 2CH3), 3.32 (m, 2H), 3.65 (m, 1H), 7.45 (s, 1H), 8.30 (s, 1H), 8.40 (br s, 2H, NH). ESI-MS m/z 293.3 (MH+).

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-30ef4b9ba7bf41d7b81a368385b69a4c
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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