Water → HCID 178512657, compound

HRID 1067225Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

NaH (13.6 mg, 80% dispersion by wt in mineral oil, 0.45 mmol) was added in one portion to a solution of guanidine hydrochloride (44 mg, 0.46 mmol) in DMSO (2 mL) and the mixture was heated at 80° C. under N2 for 10 min. 1,4-Dichloro-7-(phenylsulfanyl)isoquinoline (60 mg, 0.195 mmol) was added and the mixture heated at 80° C. for 1 h. The cooled mixture was poured into water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was extracted with hexanes-i-Pr2O and this organic solution was decanted, and then stirred with a solution of HCl in Et2O to give a precipitate. The white solid was collected by filtration and dried in vacuo to give 4-chloro-1-guanidino-7-(phenylsulphanyl)isoquinoline (51 mg, 0.13 mmol).

Workup

temperaturethe mixture heated at 80° C. for 1 h
extractionextracted with EtOAc (3×15 mL)
washThe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
customevaporated in vacuo
extractionThe residue was extracted with hexanes-i-Pr2O
customthis organic solution was decanted
customto give a precipitate
filtrationThe white solid was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-e4494183f67a434da14a35f026570523
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248738B1

Reaction notes

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