Isonicotinic Acid → isonicotinic 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 411769

Reaction equation

HRID 411769 reaction equation
CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C.[N:22]1[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=1.O[CH2:32][N:33]1[C:37](=[O:38])[C:36]([C:39]2[C:47]3[C:42](=[CH:43][C:44]([N+:48]([O-:50])=[O:49])=[CH:45][CH:46]=3)[N:41]([CH3:51])[CH:40]=2)=[C:35]([C:52]2[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[N:54]([CH3:61])[CH:53]=2)[C:34]1=[O:62]>C(Cl)Cl>[CH3:61][N:54]1[C:55]2[C:60](=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:52]([C:35]2[C:34](=[O:62])[N:33]([CH2:32][O:29][C:28](=[O:30])[C:25]3[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=3)[C:37](=[O:38])[C:36]=2[C:39]2[C:47]3[C:42](=[CH:43][C:44]([N+:48]([O-:50])=[O:49])=[CH:45][CH:46]=3)[N:41]([CH3:51])[CH:40]=2)=[CH:53]1

Participants

6

Reactant 4

HCID 5922Isonicotinic AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 9871825isonicotinic 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 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethylaminopyridine (1.5 equivalents) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.5 equivalent) in CH2Cl2 was added 4-picolinic acid (1.2 equivalents) and the reaction mixture was stirred a few minutes. 1-Hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione, prepared as in example 1a, was added and the reaction mixture was stirred at room temperature for several hours. The mixture was diluted with dichloromethane, washed with aqueous HCL, saturated NaHCO3, water, dried over MgSO4 and evaporated. The residue was purified by column chromatography to afford isonicotinic 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 (yield—76%).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for several hours
  3. washwashed with aqueous HCL, saturated NaHCO3, water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-69835ae76d5144569ca28fdf7721c8a5
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Linked notes

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