HCID 178488447, compound → HCID 178488481, compound

HRID 1067219Notes

Reaction equation

HRID 1067219 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[C:5]([NH:20][C:21]([NH2:23])=[NH:22])=[N:4][CH:3]=1>[Pd].CO>[NH3:4].[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:8]2[CH:7]=[C:6]3[C:11]([CH:2]=[CH:3][N:4]=[C:5]3[NH:20][C:21]([NH2:23])=[NH:22])=[CH:10][CH:9]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 1

HCID 178488447HCID 178488447, compound

Product 2

HCID 222AmmoniaHCID 178488481HCID 178488481, compoundYield 160%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (4-bromo-7-(4-methoxyphenyl)isoquinolin-1-yl)guanidine (38 mg, 0.1 mmol) in industrial methylated spirits (2.0 mL) containing 5% Pd-C (10 mg) was stirred under an atmosphere of H2 (3.5 atmospheres) at 23° C. for 3 days. The mixture was filtered through Arbocel™ with ethanol rinsing, the filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:3:0.3) as eluant to give (7-(4-methoxyphenyl)isoquinolin-1-yl)guanidine (24 mg, 0.08 mmol) as a white solid.

Workup

  1. filtrationThe mixture was filtered through Arbocel™ with ethanol rinsing
  2. customthe filtrate was evaporated in vacuo
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-210958c296b449c3b0ff673db1899b96
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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