trans-Crotonyl chloride → N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-(E)-2-butenamide

HRID 1823394Notes

Reaction equation

HRID 1823394 reaction equation
[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:24][CH2:25][CH2:26][CH3:27])[N:20]([CH2:21][CH2:22][NH2:23])[C:16]=2[C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1>>[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:24][CH2:25][CH2:26][CH3:27])[N:20]([CH2:21][CH2:22][NH:23][C:1](=[O:5])/[CH:2]=[CH:3]/[CH3:4])[C:16]=2[C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 643131trans-Crotonyl chlorideHCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine

Product 1

HCID 22172724N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-(E)-2-butenamideYield 81.1%

Procedure

Using the general method of Example 92, crotonyl chloride (68 μL, 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) to provide 0.2 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-(E)-2-butenamide as a white powder, m.p. 198–200° C. Analysis: Calculated for C19H24N6O: % C, 64.75; % H, 6.86; % N, 23.85; Found: % C, 64.25; % H, 6.68; % N, 23.99. HRMS (EI) calcd for C19H24N6O (M+) 352.2011 found 352.1996.

Sources & evidence

ORD record
ord-10d3e9388981469bbd25314b740e2a20
Source dataset
uspto-grants-2006_05
Patent number
US07038051B2

Reaction notes

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