Triethylamine → HCID 178454277, compound

HRID 1067217Notes

Reaction equation

HRID 1067217 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:12]([O:16][C:17]([NH:19][C:20](=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])SC)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl.[Hg](Cl)Cl>[C:27]([O:26][C:24]([NH:23][C:20](=[N:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[NH:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 311869Isoquinolin-3-AmineHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 178454277HCID 178454277, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Mercury (II) chloride (192 mg, 0.707 mmol) was added in one portion to a stirred mixture of 3-aminoisoquinoline (84.5 mg, 0.586 mmol), N,N′-di-t-butoxycarbonyl-S-methylisothiourea (Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700-1703) (204 mg, 0.703 mmol), and triethylamine (250 μL, 1.79 mmol) in CH2Cl2 (3.0 mL) under N2 at 23° C. The mixture was stirred for 26 hours and then directly purified by column chromatography upon silica gel using hexanes-EtOAc (98:2 to 95:5) as eluant to give 3-(N′,N″-di-t-butoxycarbonyl-N-guanidinyl)isoquinoline (189.4 mg, 0.492 mmol) as a white solid.

Workup

  1. customdirectly purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-4afb8dccad0843ffa82217885c220f41
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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