Sodium Bicarbonate → HCID 178478923, compound

HRID 1018712Notes

Reaction equation

HRID 1018712 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([NH:15][C:16]([C:18]3[N:19]([CH3:26])[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=3)=[O:17])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:28](O)=[O:29].[ClH:31].Cl.[NH2:33][CH2:34][CH2:35][NH:36][C:37]([NH2:39])=[NH:38].O.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[ClH:31].[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([NH:15][C:16]([C:18]3[N:19]([CH3:26])[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=3)=[O:17])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:28]([NH:33][CH2:34][CH2:35][NH:36][C:37]([NH2:39])=[NH:38])=[O:29]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 11729362HCID 11729362, compoundHCID 178478821HCID 178478821, compound

Product 1

HCID 178478923HCID 178478923, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-methyl-4[1-methyl-4[1-methyl-4-nitropyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxylic acid (590 mg) (prepared as reported in Tetrahedron 34,2389-2391,1978) in 20 ml of DMF, 2-aminoethylguanidine dihydrochloride (500 mg), 1-hydroxybenzotriazole hydrate (350 mg), dicycloexylcarbodiimide (880 mg), and sodium bicarbonate (385 mg) was stirred at 70° C. for 4 hours. The solution obtained after filtration was evaporated in vacuo and the residue purified by flash chromatography (methylene chloride/methanol: 8/2) to yield 800 mg of 2-[1-methyl-4[1-methyl-4[1-methyl-4-nitropyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]ethylguanidine hydrochloride, which was dissolved in methanol (100 ml), added with 1N hydrochloric acid solution (2 ml) and reduced over Pd catalyst (100 on charcoal) in hydrogen atmosphere (50 psi) in a Parr apparatus. The solution obtained after filtration of the catalyst was evaporated in vacuo and the solid residue washed with dry ethanol to yield 750 mg of the intermediate as a brown powder.

Workup

  1. customThe solution obtained
  2. filtrationafter filtration
  3. customwas evaporated in vacuo
  4. customthe residue purified by flash chromatography (methylene chloride/methanol: 8/2)

Sources & evidence

ORD record
ord-abb45d6eeb164f3fa3c4acd57d5fff80
Source dataset
uspto-grants-2002_11
Patent number
US06482920B1

Reaction notes

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