Citronellic acid → N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,7-dimethyl-6-octenamide

HRID 352523

Reaction equation

HRID 352523 reaction equation
[C:1]([OH:12])(=O)[CH2:2][CH:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:4].[NH2:13][C:14]1[C:23]2[N:24]=[C:25]([CH2:30][CH2:31][CH2:32][CH3:33])[N:26]([CH2:27][CH2:28][NH2:29])[C:22]=2[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1>>[NH2:13][C:14]1[C:23]2[N:24]=[C:25]([CH2:30][CH2:31][CH2:32][CH3:33])[N:26]([CH2:27][CH2:28][NH:29][C:1](=[O:12])[CH2:2][CH:3]([CH3:4])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])[C:22]=2[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

3

Reactant 2

HCID 10402Citronellic acidHCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine

Product 1

HCID 12112193N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,7-dimethyl-6-octenamideYield 67.4%

Procedure

Using the general method of Example 97 citronellic acid (0.3 g, 1.7 mmole) was reacted with 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine (0.5 g, 1.7 mmol) to provide 0.5 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,7-dimethyl-6-octenamide as a white whispy solid, m.p. 163-164° C. Analysis: Calculated for C25H36N6O: %C, 68.77; %H, 8.31; %N, 19.25; Found: %C, 68.84; %H, 8.14; %N, 19.58. HRMS (EI) calcd for C25H36N6O (M+) 436.2950 found 436.2952.

Sources & evidence

ORD record
ord-17f150586a3a4e1793dfab51adb16917
Source dataset
uspto-grants-2004_06
Patent number
US06747040B2

Linked notes

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