Ethyl chloroformate → ethyl N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate

HRID 47488Notes

Reaction equation

HRID 47488 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:26][CH2:27][CH2:28][CH3:29])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])[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]([CH2:26][CH2:27][CH2:28][CH3:29])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:2](=[O:3])[O:4][CH2:5][CH3:6])[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 10928Ethyl chloroformateHCID 129926164-(4-amino-2-butyl 1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butaneamine

Product 1

HCID 12987865ethyl N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamateYield 81.3%

Procedure

Using the general method of Example 55, ethyl chloroformate (46 μL, 0.48 mmol) was reacted with 4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butaneamine (0.15 g, 0.48 mmol) to provide 0.15 g of ethyl N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate as a white powder. Analysis: Calculated for C20H28N6O2: %C, 62.48; %H, 7.34; %N, 21.86. Found: %C, 61.73; %H, 7.28; %N, 21.62.

Sources & evidence

ORD record
ord-e01767377a7f4e5599ce3b4c8ca4b507
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Reaction notes

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