Guanidine Hydrochloride → HCID 178512627, compound

HRID 1067222Notes

Reaction equation

HRID 1067222 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[H-].[Na+].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19](=[O:28])(=[O:27])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=2)[CH:12]=[CH:11][N:10]=1>CS(C)=O>[NH:4]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19](=[O:28])(=[O:27])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=2)[CH:12]=[CH:11][N:10]=1)[C:3]([NH2:5])=[NH:2]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 24758Sodium hydrideHCID 16658410HCID 16658410, compound

Product 1

HCID 178512627HCID 178512627, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Guanidine hydrochloride (100 mg, 1.05 mmol) was added in one portion to a suspension of sodium hydride (NaH) (30 mg, 80% dispersion by wt. in mineral oil, 1.0 mmol) in dimethylsulphoxide (DMSO) (3.5 mL) and the mixture was heated at 60° C. under nitrogen (N2) for 30 minutes. 1-Chloro-7-phenylsulphamoylisoquinoline (110 mg, 0.345 mmol) was added and the mixture was heated at 100° C. for 3 d. The solvents were evaporated in vacuo and the residue was purified by column chromatography (silica gel using CH2Cl2-methanol-0.880NH3 (97:3:0.3 to 90:10:1) as eluant) to give 1-guanidino-7-phenylsulphamoylisoquinoline (16 mg, 0.047 mmol) as an off-white solid.

Workup

  1. temperaturethe mixture was heated at 100° C. for 3 d
  2. customThe solvents were evaporated in vacuo
  3. customthe residue was purified by column chromatography (silica gel using CH2Cl2-methanol-0.880NH3 (97:3:0.3 to 90:10:1) as eluant)

Sources & evidence

ORD record
ord-0bd845c172874595b34a144f9d9b031a
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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