Potassium Hydroxide → HCID 178524321, compound

HRID 368328Notes

Reaction equation

HRID 368328 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14][CH2:13]3)[N:4]=[CH:3]1.C([CH2:24][C:25]1[S:29][C:28]([CH:30]=[O:31])=[CH:27][CH:26]=1)(O)=O.[OH-:32].[K+]>CCO>[NH:2]1[CH:6]=[C:5]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[C:15](=[CH:24][C:25]2[S:29][C:28]([C:30]([OH:31])=[O:32])=[CH:27][CH:26]=2)[CH2:14][CH2:13]3)[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 186265125-Carboxymethyl-2-thiophene carboxaldehydeHCID 178479625HCID 178479625, compound

Product 1

HCID 178524321HCID 178524321, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the method of Example 34, 6-[2-(1H-imidazole-4-yl)-ethoxy]-3,4-dihydro-2H-naphthalen-1-one, monohydrochloride (0.220 g, 0.75 mmol) was reacted with 5-carboxymethyl-2-thiophene carboxaldehyde (0.191 g, 1.12 mmol) in 5 mL of 4% KOH in EtOH overnight, and the resulting solid was purified by preparative HPLC (C18, 0.1% TFA in H2O:0.1% TFA in AcCN; gradient 80:20 to 20:80) to afford 0.302 g (75%) of the title compound as a light tan powder, mp dec. >200° C.: APCI-MS m/e 395 (M+ +1).

Workup

  1. customthe resulting solid was purified by preparative HPLC (C18, 0.1% TFA in H2O:0.1% TFA in AcCN; gradient 80:20 to 20:80)

Sources & evidence

ORD record
ord-40a70ce756b24e629ec6ba5cebc1361a
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

Loading…