e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

General method for the synthesis of selectively N-alkylated polyamines

…, MJ Payne, MA Balk, JL Gress, FD Harris…

Index: Nordlander, J. Eric; Payne, Mark J.; Balk, Michael A.; Gress, Julia L.; Harris, Frederick D.; et al. Journal of Organic Chemistry, 1984 , vol. 49, p. 133 - 138

Full Text: HTML

Citation Number: 25

Abstract

A versatile method is presented for the synthesis of linear polyamines-in particular, the naturally ubiquitous putrescine, spermidine, and spermine-regiospecifically N-alkylated or N- polyalkylated. The new approach is based on the acylation of amines with N-(trifluoroacety1) amino acid chlorides, optional alkylation followed by selective saponification of the (trifluoroacetylhnino function, analogous reacylation, and polyamide to polyamine ...

3-[(2,2,2-trifluoroacetyl)amino]propanoic acid Structure

3-[(2,2,2-trifl...

~%

N-benzyl-3-[(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[(2,...

N-trifluoroacetyl-β-alanyl chloride Structure

N-trifluoroacet...

Benzylamine Structure

~%

N-benzyl-3-[(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[(2,...

Piperidine Structure

N-(Trifluoroacetyl)-γ-aminobutyric Acid Chloride Structure

N-(Trifluoroace...

~%

2,2,2-trifluoro-N-(4-oxo-4-piperidin-1-ylbutyl)acetamide Structure

2,2,2-trifluoro...

N-(Trifluoroacetyl)-γ-aminobutyric Acid Chloride Structure

N-(Trifluoroace...

N-Ethylaniline Structure

~%

N-ethyl-N-phenyl-4-[(2,2,2-trifluoroacetyl)amino]butanamide Structure

N-ethyl-N-pheny...

N-(Trifluoroacetyl)-γ-aminobutyric Acid Chloride Structure

N-(Trifluoroace...

Dimethylamine Structure

~%

N,N-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]butanamide Structure

N,N-dimethyl-4-...

N-benzyl-3-[(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[(2,...

methyl iodide Structure

~65%

N-benzyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[met...

3-[(2,2,2-trifluoroacetyl)amino]propanoic acid Structure

3-[(2,2,2-trifl...

~%

N-benzyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[met...

N-trifluoroacetyl-β-alanyl chloride Structure

N-trifluoroacet...

~%

N-benzyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[met...

N-benzyl-2,2,2-trifluoro-N-(2-morpholino-2-oxoethyl)acetamide Structure

N-benzyl-2,2,2-...

~51%

2-(benzylamino)-1-morpholin-4-ylethanone Structure

2-(benzylamino)...

2,2,2-trifluoro-N-(2-morpholin-4-yl-2-oxoethyl)acetamide Structure

2,2,2-trifluoro...

~%

2-(benzylamino)-1-morpholin-4-ylethanone Structure

2-(benzylamino)...

N-benzyl-3-[methyl-(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[met...

~88%

N-benzyl-3-(methylamino)propanamide Structure

N-benzyl-3-(met...

N-benzyl-3-[(2,2,2-trifluoroacetyl)amino]propanamide Structure

N-benzyl-3-[(2,...

~%

N-benzyl-3-(methylamino)propanamide Structure

N-benzyl-3-(met...

2,2,2-trifluoro-N-(4-oxo-4-piperidin-1-ylbutyl)acetamide Structure

2,2,2-trifluoro...

~51%

4-amino-1-piperidin-1-ylbutan-1-one Structure

4-amino-1-piper...

Piperidine Structure

~%

4-amino-1-piperidin-1-ylbutan-1-one Structure

4-amino-1-piper...

2,2,2-trifluoro-N-(2-morpholin-4-yl-2-oxoethyl)acetamide Structure

2,2,2-trifluoro...

~%

benzyl[2-(morpholin-4-yl)ethyl]amine Structure

benzyl[2-(morph...

N-benzyl-2,2,2-trifluoro-N-(2-morpholino-2-oxoethyl)acetamide Structure

N-benzyl-2,2,2-...

~%

benzyl[2-(morpholin-4-yl)ethyl]amine Structure

benzyl[2-(morph...

2-(benzylamino)-1-morpholin-4-ylethanone Structure

2-(benzylamino)...

~%

benzyl[2-(morpholin-4-yl)ethyl]amine Structure

benzyl[2-(morph...

morpholine Structure

(2,2,2-Trifluoro-acetylamino)-acetyl chloride Structure

(2,2,2-Trifluor...

~%

2,2,2-trifluoro-N-(2-morpholin-4-yl-2-oxoethyl)acetamide Structure

2,2,2-trifluoro...

N,N-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]butanamide Structure

N,N-dimethyl-4-...

~%

4-amino-N,N-dimethylbutanamide(SALTDATA: HCl) Structure

4-amino-N,N-dim...

4-amino-N,N-dimethylbutanamide(SALTDATA: HCl) Structure

4-amino-N,N-dim...

~%

N-[3-[[4-(dimethylamino)-4-oxobutyl]amino]-3-oxopropyl]benzamide Structure

N-[3-[[4-(dimet...

N,N-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]butanamide Structure

N,N-dimethyl-4-...

~%

N-[3-[[4-(dimethylamino)-4-oxobutyl]amino]-3-oxopropyl]benzamide Structure

N-[3-[[4-(dimet...

N,N-dimethyl-4-(3-(2,2,2-trifluoroacetamido)propanamido)butanamide Structure

N,N-dimethyl-4-...

~%

N-[3-[[4-(dimethylamino)-4-oxobutyl]amino]-3-oxopropyl]benzamide Structure

N-[3-[[4-(dimet...