Guanidine Hydrochloride → HCID 178451317, compound

HRID 2289702Notes

Reaction equation

HRID 2289702 reaction equation
FC(F)(F)C(O)=O.[Cl:8]C1N=C(NC(N)=N)C2C(C=1)=CC=C(S(NCC(O)=O)(=O)=O)C=2.Cl.[NH2:32][C:33]([NH2:35])=[NH:34].[C:36]([O:40][C:41](=[O:59])[CH2:42][NH:43][S:44]([C:47]1[CH:56]=[C:55]2[C:50]([C:51]([Cl:58])=[CH:52][N:53]=[C:54]2Cl)=[CH:49][CH:48]=1)(=[O:46])=[O:45])([CH3:39])([CH3:38])[CH3:37]>CS(C)=O.O>[ClH:8].[C:36]([O:40][C:41](=[O:59])[CH2:42][NH:43][S:44]([C:47]1[CH:56]=[C:55]2[C:50]([C:51]([Cl:58])=[CH:52][N:53]=[C:54]2[NH:34][C:33]([NH2:35])=[NH:32])=[CH:49][CH:48]=1)(=[O:45])=[O:46])([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 16658414HCID 16658414, compoundHCID 178512683HCID 178512683, compound

Product 1

HCID 178451317HCID 178451317, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-[(-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine trifluoroacetate ##STR13## NaH (29 mg, 80% dispersion by wt in mineral oil, 0.97 mmol) was added in one portion to a stirred solution of guanidine hydrochloride (146 mg, 1.52 mmol) in DMSO (2.0 mL) and the mixture was heated at 60° C. under N2 for 30 min. N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]glycine t-butyl ester (150 mg, 0.38 mmol) was added and the mixture heated at 90° C. for 9 h. The cooled mixture was diluted with water (30 mL), extracted with EtOAc (4×20 mL) and the combined organic extracts were washed with water, brine, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in Et2O and a solution of HCl in Et2O (1 M) was added to give a sticky precipitate. The Et2O was decanted and the residue triturated with EtOAc to give a white solid. Filtration with EtOAc and Et2O washing gave N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine t-butyl ester hydrochloride (68 mg, 0.14 mmol).

Workup

  1. temperaturethe mixture heated at 90° C. for 9 h
  2. extractionextracted with EtOAc (4×20 mL)
  3. washthe combined organic extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in Et2O
  7. additiona solution of HCl in Et2O (1 M) was added
  8. customto give a sticky precipitate
  9. customThe Et2O was decanted
  10. customthe residue triturated with EtOAc
  11. customto give a white solid
  12. filtrationFiltration with EtOAc and Et2O washing

Sources & evidence

ORD record
ord-480339ce65af456d8f3e7b23ad4caa82
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

Loading…