Dichloromethane → HCID 86759565, compound

HRID 2416585Notes

Reaction equation

HRID 2416585 reaction equation
Br.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[CH:5][N:4]=1.[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH2:35]Cl)[CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:35][C@H:22]([NH:21][C:19]([O:18][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:20])[CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 22631312HCID 22631312, compoundHCID 86588383benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate

Product 1

HCID 86759565HCID 86759565, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

8.81 g (27 mmol) of 1-amino-7-hydroxyisoquinoline monohydrobromide was dissolved in 120 ml of DMF. 14.0 g (41 mmol) of benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate, 11.2 g (81.0 mmol) of potassium carbonate and 9.96 g (27 mmol) of tetrabutylammonium iodide were added to the obtained solution, and they were stirred at 70° C. for 3 days. After the treatment with dichloromethane as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-489b8aa5a3cf45859ffddb56a79f4d1e
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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