N,N-Diethylethylenediamine → (2-dimethylamino-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester

HRID 411776

Reaction equation

HRID 411776 reaction equation
[OH:1][CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[C:5]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)[C:4]1=[O:32].[N+](C1C=C[C:39]([O:42]C(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.[CH2:55]([N:57]([CH2:60][CH2:61][NH2:62])[CH2:58]C)C>C1COCC1>[CH3:31][N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:5]2[C:4](=[O:32])[N:3]([CH2:2][O:1][C:39](=[O:42])[NH:62][CH2:61][CH2:60][N:57]([CH3:58])[CH3:55])[C:7](=[O:8])[C:6]=2[C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[CH:23]1

Participants

5

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 78756Bis(4-nitrophenyl) carbonateHCID 98673381-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Product 1

HCID 9893615(2-dimethylamino-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl esterYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (200 mg, 0.47 mmol), prepared as in example 1a, was dissolved in THF (10 mL). The resulting red solution was cooled in an ice bath. Lithium bis(trimethylsiliyl)amide (0.56 mL, 0.56 mmol, 1 M in THF) was added dropwise to the solution to give a red suspension. After 10 min, bis(p-nitrophenyl)carbonate (200 mg, 0.66 mmol) was added. The resulting solution was stirred at 0° C. for 20 min. Diethylaminoethylamine (90 mg, 0.78 mmol) in THF (2 mL) was added. Stirring was continued for 2 hrs. The mixture was evaporated and the residue was purified by flash chromatography to give (2-dimethylamino-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (124 mg 46%).

Workup

  1. temperatureThe resulting red solution was cooled in an ice bath
  2. customto give a red suspension
  3. stirringStirring
  4. waitwas continued for 2 hrs
  5. customThe mixture was evaporated
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1d1ee7fff9e34af1a5d27df8ceb736b7
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Linked notes

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