Benzenepropanoyl chloride → HCID 22172678, compound

HRID 989122Notes

Reaction equation

[C:1]([Cl:11])(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12][C:13]1[C:22]2[N:23]=[C:24]([CH2:29][CH2:30][CH2:31][CH3:32])[N:25]([CH2:26][CH2:27][NH2:28])[C:21]=2[C:20]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1>>[ClH:11].[NH2:12][C:13]1[C:22]2[N:23]=[C:24]([CH2:29][CH2:30][CH2:31][CH3:32])[N:25]([CH2:26][CH2:27][NH:28][C:1](=[O:10])[CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:21]=2[C:20]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

Reactant 2

HCID 64801Benzenepropanoyl chloride

HCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine

Product 1

HCID 22172678HCID 22172678, compoundYield 63.1%

Procedure

Using the general method of Example 92, hydrocinnamoyl chloride (0.1 g, 0.7 mmol) was reacted with 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine (0.2 g, 0.7 mmol). After one hour the reaction mixture was poured directly onto a silica gel column and eluted with dichloromethane at first, then 15% methanol/dichloromethane to provide 0.2 g of a solid. This solid was recrystallized from toluene to provide 0.2 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]([1,5]naphthyridin-1-yl)ethyl]-3-phenylpropanamide hydrochloride as a white powder, m.p. 183-185° C. Analysis: Calculated for C24H28N6O HCl: %C, 63.64; %H, 6.45; %N, 18.55; Found: %C, 63.68; %H, 6.43; %N, 18.55.

Workup

additionAfter one hour the reaction mixture was poured directly onto a silica gel column
washeluted with dichloromethane at first, then 15% methanol/dichloromethane

Sources & evidence

ORD record: ord-aed8922878054c31b89bd63982942279
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638944B2

Reaction notes

Loading…