Guanidine Hydrochloride → HCID 178451238, compound

HRID 2289719Notes

Reaction equation

HRID 2289719 reaction equation
FC(F)(F)C(O)=O.[Cl:8]C1C2C(=CC(S(N(CC3C=CC=C(Cl)C=3)CC(O)=O)(=O)=O)=CC=2)C(NC(N)=N)=NC=1.Cl.[NH2:40][C:41]([NH2:43])=[NH:42].[C:44]([O:48][C:49](=[O:75])[CH2:50][N:51]([S:60]([C:63]1[CH:72]=[C:71]2[C:66]([C:67]([Cl:74])=[CH:68][N:69]=[C:70]2Cl)=[CH:65][CH:64]=1)(=[O:62])=[O:61])[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([Cl:59])[CH:54]=1)([CH3:47])([CH3:46])[CH3:45]>COCCOC.CCOCC>[ClH:8].[C:44]([O:48][C:49](=[O:75])[CH2:50][N:51]([S:60]([C:63]1[CH:72]=[C:71]2[C:66]([C:67]([Cl:74])=[CH:68][N:69]=[C:70]2[NH:42][C:41]([NH2:43])=[NH:40])=[CH:65][CH:64]=1)(=[O:61])=[O:62])[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([Cl:59])[CH:54]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 18698258HCID 18698258, compoundHCID 178512672HCID 178512672, compound

Product 1

HCID 178451238HCID 178451238, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(3-chlorobenzyl)glycine trifluoroacetate ##STR23## NaH (35 mg, 80% dispersion by wt in mineral oil, 1.16 mmol) was added in one portion to a suspension of guanidine hydrochloride (150 mg, 1.55 mmol) in DME (10 mL) and the mixture was heated at 60° C. under N2 for 30 min. N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-N-(3-chlorobenzyl)glycine t-butyl ester (185 mg, 0.36 mmol) was added and the mixture heated at 90° C. for 5 h. The cooled mixture was diluted with Et2O, washed with water, 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 precipitate. The solvents were evaporated in vacuo, and the white solid triturated with EtOAc and then dried to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(3-chlorobenzyl)glycine t-butyl ester hydrochloride (85 mg, 0.145 mmol).

Workup

  1. temperaturethe mixture heated at 90° C. for 5 h
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in Et2O
  6. additiona solution of HCl in Et2O (1 M) was added
  7. customto give a precipitate
  8. customThe solvents were evaporated in vacuo
  9. customthe white solid triturated with EtOAc
  10. customdried

Sources & evidence

ORD record
ord-e63166ae7aee47ae8c1dd3ad1ad86afb
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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