Water → HCID 178512659, compound

HRID 1067226Notes

Reaction equation

HRID 1067226 reaction equation
[H-].[Na+].Cl.[NH2:4][C:5]([NH2:7])=[NH:6].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:17]=2)[C:12]([Cl:28])=[CH:11][N:10]=1.O>CS(C)=O>[Cl:28][C:12]1[C:13]2[C:18](=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:21])=[CH:15][CH:14]=2)[C:9]([NH:6][C:5]([NH2:7])=[NH:4])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 24758Sodium hydrideHCID 21192426HCID 21192426, compound

Product 1

HCID 178512659HCID 178512659, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

NaH (18 mg, 80% dispersion by wt in mineral oil, 0.60 mmol) was added in one portion to a solution of guanidine hydrochloride (90 mg, 0.94 mmol) in DMSO (2 mL) and the mixture was heated at 50° C. under N2 for 30 min. 1,4-Dichloro-7-(phenylsulfonyl)isoquinoline (80 mg, 0.236 mmol) was added and the mixture heated at 50-60 C. for 0.5 h. The cooled mixture was poured into water (30 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in EtOAc and a solution of HCl in Et2O (1 M) was added which gave a precipitate. The solvents were evaporated in vacuo and the residue triturated with EtOAc to give 4-chloro-1-guanidino-7-(phenylsulphonyl)isoquinoline (65 mg, 0.18 mmol) as a yellow solid.

Workup

  1. temperaturethe mixture heated at 50-60 C
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. additiona solution of HCl in Et2O (1 M) was added which
  8. customgave a precipitate
  9. customThe solvents were evaporated in vacuo
  10. customthe residue triturated with EtOAc

Sources & evidence

ORD record
ord-1a482d92753447dfa745a96005f0fd9c
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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