Water → HCID 178431816, compound

HRID 1582225Notes

Reaction equation

HRID 1582225 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].N1C=CC=CC=1.[S:15]([OH:35])([O:18][C:19]1[C:20]([CH3:34])=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[C:23]([C:29](OCC)=[O:30])=[CH:22]2)(=[O:17])=[O:16].O>CN(C)C=O>[S:15]([OH:35])([O:18][C:19]1[C:20]([CH3:34])=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[C:23]([C:29]([NH:7][C:6]([NH2:8])=[NH:5])=[O:30])=[CH:22]2)(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 22719997HCID 22719997, compound

Product 1

HCID 178431816HCID 178431816, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of sodium methoxide (4.28 g, 79.2 mmol), guanidine hydrochloride (7.58 g, 79.3 mmol) and N,N-dimethylformamide (70 ml) was stirred at room temperature for 1 hour, and then the insoluble material was filtered off. A solution of 2-ethoxycarbonyl-1,4-dimethyl-1H-indole-5-yl hydrogen sulfate pyridine salt (3.11 g, 7.92 mmol) in N,N-dimethylformamide (10 ml) was added to the filtrate, and the resulting mixture was stirred at room temperature for 7.5 hours. Water was added to the reaction mixture, followed by washing with chloroform. Subsequently, chloroform and then 2N hydrochloric acid were added and the solid thus precipitated was collected by filtration and washed with methanol to obtain 2.12 g of 2-[[[amino(imino)-methyl]amino]carbonyl]-1,4-dimethyl-1H-indol-5-yl hydrogen sulfate.

Workup

  1. filtrationthe insoluble material was filtered off
  2. stirringthe resulting mixture was stirred at room temperature for 7.5 hours
  3. washby washing with chloroform
  4. additionSubsequently, chloroform and then 2N hydrochloric acid were added
  5. customthe solid thus precipitated
  6. filtrationwas collected by filtration
  7. washwashed with methanol

Sources & evidence

ORD record
ord-037b4ad781624dda99ca11115e5c1d23
Source dataset
uspto-grants-2004_05
Patent number
US06734205B2

Reaction notes

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