Guanidine Hydrochloride → HCID 178512626, compound

HRID 1067220Notes

Reaction equation

HRID 1067220 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]([NH2:22])(=[O:21])=[O:20])[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:21])(=[O:20])[NH2:22])[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 16658630HCID 16658630, compound

Product 1

HCID 178512626HCID 178512626, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Guanidine hydrochloride (42 mg, 0.44 mmol) was added in one portion to a suspension of NaH (13 mg, 80% dispersion by wt in mineral oil, 0.43 mmol) in DMSO (1.5 mL) and the mixture was heated at 60° C. under N2 for 30 min. 1-Chloro-7-isoquinolinesulphonamide (37 mg, 0.152 mmol) was added and the mixture heated at 100° C. for 24 h. The solvents were evaporated in vacuo and the residue was purified by column chromatography upon silica gel using CH2Cl2—MeOH-0.880NH3 (97:3:0.3 to 90:10:1) as eluant to give the title compound (34 mg, 0.13 mmol) as an off-white solid.

Workup

  1. temperaturethe mixture heated at 100° C. for 24 h
  2. customThe solvents were evaporated in vacuo
  3. customthe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-2358ba62b55b4d3d9ac394a769822248
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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