Ammonia → N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide

HRID 650073Notes

Reaction equation

HRID 650073 reaction equation
[OH:1][CH:2]1[C:11]2[C:6]3=[C:7]([CH:13]=[C:14]([C:15]([O:17]CC)=O)[N:5]3[CH2:4][CH2:3]1)[C:8]([CH3:12])=[CH:9][CH:10]=2.Cl.[NH2:21][C:22]([NH2:24])=N.C[O-].[Na+].[NH3:28].[CH:29](O)([CH3:31])[CH3:30]>CS(O)(=O)=O.CN(C)C=O>[NH2:28][N:21]=[CH:22][NH:24][C:15]([C:14]1[N:5]2[C:6]3[C:11]([CH:2]([O:1][CH:29]([CH3:31])[CH3:30])[CH2:3][CH2:4]2)=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=3[CH:13]=1)=[O:17]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 3776IsopropanolHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 21714278ethyl 5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo [3,2,1-ij]quinoline-2-carboxylate

Product 1

HCID 136365319N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Crude N-(aminoiminomethyl)-5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide was obtained by carrying out reaction according to the method described in Example 1, except for using ethyl 5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate (0.70 g, 2.70 mmol), guanidine hydrochloride (2.58 g, 27.0 mmol), sodium methoxide (1.46 g, 27.0 mmol) and N,N-dimethylformamide (40 ml). This compound was dissolved in a solution of methanesulfonic acid (1.0 g) in isopropanol (50 ml) and the resulting solution was stirred at 60° C. for 30 minutes. Subsequently, the reaction solution was poured into ice water, made basic with 28% aqueous ammonia and then extracted three times with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=97/3) to obtain 0.37 g of N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide. This compound was treated with methanesulfonic acid (0.29 g) in a mixed solvent of tetrahydrofuran and diethyl ether to obtain N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide methanesulfonate.

Workup

  1. customreaction
  2. extractionextracted three times with ethyl acetate
  3. washThe extract solution was washed with a 5% aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=97/3)

Sources & evidence

ORD record
ord-a6e5c4f1e4b04bb0a2c29c3093d21640
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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