Ammonia → HCID 136365320, compound

HRID 650081Notes

Reaction equation

HRID 650081 reaction equation
[Cl:1][C:2]1[C:10]([O:11]COC)=[CH:9][C:8]2[C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH2:19][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:21]([O:23]CC)=O.Cl.[NH2:27][C:28]([NH2:30])=N.C[O-].[Na+].[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[NH3:39]>O.C(O)(C)C.CN(C)C=O>[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[NH2:39][N:27]=[CH:28][NH:30][C:21]([C:5]1[N:6]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:8]3[CH:9]=[C:10]([OH:11])[C:2]([Cl:1])=[C:3]([CH:4]=1)[C:7]2=3)=[O:23]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 5742Guanidine HydrochlorideHCID 6395Methanesulfonic AcidHCID 10942334Sodium MethoxideHCID 21714298HCID 21714298, compound

Product 1

HCID 136365320HCID 136365320, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

Crude N-(aminoiminomethyl)-5,6,7,8-tetrahydro-11-chloro-10-methoxymethyloxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxamide was obtained by carrying out reaction according to the method described in Example 1, except for using ethyl 5,6,7,8-tetrahydro-11-chloro-10-methoxymethyloxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxylate (0.50 g, 1.36 mmol), guanidine hydrochloride (2.60 g, 27.2 mmol), sodium methoxide (1.47 g, 27.2 mmol) and N,N-dimethylformamide (50 ml). Subsequently, the crude product was added to a mixture of isopropanol (70 ml), water (20 ml) and methanesulfonic acid (0.50 g), and the resulting mixture was stirred at 65-70° C. for 6 hours. The reaction mixture was neutralized with 28% aqueous ammonia and extracted three times with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was dissolved in tetrahydrofuran (70 ml), after which methanesulfonic acid (0.26 g) was added and the solid precipitated was collected by filtration. The solid collected was recrystallized from a mixture of isopropanol (1 ml) and water (20 ml) to obtain 0.25 g of N-(aminoiminomethyl)-5,6,7,8-tetrahydro-11-chloro-10-hydroxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxamide methanesulfonate.

Workup

  1. customreaction
  2. extractionextracted three times with ethyl acetate
  3. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. dissolutionthe resulting residue was dissolved in tetrahydrofuran (70 ml)
  7. additionafter which methanesulfonic acid (0.26 g) was added
  8. customthe solid precipitated
  9. filtrationwas collected by filtration
  10. customThe solid collected
  11. customwas recrystallized from a mixture of isopropanol (1 ml) and water (20 ml)

Sources & evidence

ORD record
ord-d4e66b730b9a41c5b57bbc411270830f
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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