62009-47-6

Usage

Uses

Used in Chemical Synthesis:
2-aminopropanediamide is used as a reagent for the synthesis of imidazole derivatives. Imidazole derivatives are a class of compounds with a wide range of applications, including pharmaceuticals, agrochemicals, and materials science. The use of 2-aminopropanediamide in this context is due to its ability to act as a precursor, facilitating the formation of the desired imidazole structures.

InChI:InChI=1/C3H7N3O2/c4-1(2(5)7)3(6)8/h1H,4H2,(H2,5,7)(H2,6,8)

Synthetic route

aminomalonic acid diethyl ester (6829-40-9) → 2-aminopropanediamide (62009-47-6)

Conditions	Yield
With ammonia In methanol at 80℃;	100%
With ammonium chloride In water at 100℃; for 2h;	87%
With ammonia In methanol at 60℃; for 19h; Product distribution / selectivity; Inert atmosphere;	49%
With ethanol; ammonia

diethyl aminomalonate hydrochloride (13433-00-6) → 2-aminopropanediamide (62009-47-6)

Conditions	Yield
With ammonia In methanol at 20℃; for 20h; Autoclave;	95%
With ammonia In methanol for 1h;	91%
Stage #1: diethyl aminomalonate hydrochloride With sodium hydrogencarbonate In water pH=> 7; Stage #2: With ammonia In methanol at 80℃; High pressure;	73%

diethyl 2-chloromalonate (14064-10-9) → 2-aminopropanediamide (62009-47-6)

Conditions	Yield
With ethanol; ammonia

2-nitromalonamide (69645-51-8) → 2-aminopropanediamide (62009-47-6)

Conditions	Yield
With aluminium amalgam; ammonia

diethyl 2-chloromalonate (14064-10-9) + ammonia (7664-41-7) → 2-aminopropanediamide (62009-47-6)

aminomalonic acid ester hydrochloride → 2-aminopropanediamide (62009-47-6)

Conditions	Yield
With ammonia; water

isonitrosomalonamide → 2-aminopropanediamide (62009-47-6)

Conditions	Yield
With hydrogen iodide durch Reduktion;

2-aminopropanediamide (62009-47-6) + di-tert-butyl dicarbonate (24424-99-5) → C8H15N3O4

Conditions	Yield
Stage #1: 2-aminopropanediamide; di-tert-butyl dicarbonate In methanol at 0 - 4℃; for 1h; Stage #2: With triethylamine In methanol at 22 - 27℃; for 18h; pH=10-12;	94.78%

Glyoxal (131543-46-9) + 2-aminopropanediamide (62009-47-6) → sodium 2-carbamoylpyrazine-3-hydroxylate (1237524-82-1)

Conditions	Yield
With sodium hydroxide In water at -10 - 22℃; for 4.66667h;	92%
With lithium chloride; sodium hydroxide at 20℃; for 3.5h; Temperature;	88.2%

Glyoxal (131543-46-9) + 2-aminopropanediamide (62009-47-6) → 2-hydroxypyrazine-3-carboxamide (55321-99-8)

Conditions	Yield
With sodium hydroxide In water at -10 - 22℃; for 4.67h;	91.2%
Stage #1: Glyoxal; 2-aminopropanediamide In water at 90℃; for 3h; Stage #2: With ammonia; dihydrogen peroxide In water at 0 - 20℃;	63%
With phosphoric acid; sodium hydroxide In water at 20 - 30℃; for 1.5h;	118 g
With phosphoric acid; sodium hydroxide In aq. phosphate buffer; water at 20 - 30℃; for 1.5h;	118 mg

ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoate + 2-aminopropanediamide (62009-47-6) → ethyl 5-(aminocarbonyl)-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate (939807-27-9)

Conditions	Yield
With trifluoroacetic acid In acetic acid at 80℃;	83.7%

2-aminopropanediamide (62009-47-6) + 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide hydrochloride → 2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6- triamine (428854-24-4)

Conditions	Yield
Stage #1: 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide hydrochloride With sodium methylate In methanol Reflux; Stage #2: 2-aminopropanediamide In methanol at 65℃; for 2.5h; Temperature; Concentration; Reflux;	83%

2-aminopropanediamide (62009-47-6) + 2-oxopropanal (78-98-8) → 3-carboxamido-2-hydroxy-6-methylpyrazine (88394-05-2)

Conditions	Yield
With sodium hydroxide In water at 5℃; for 6h; Temperature;	78%
Stage #1: 2-oxopropanal With sodium hydrogensulfite; sodium hydroxide In water at 80℃; for 1h; Stage #2: 2-aminopropanediamide In water at 80℃; for 2h; Stage #3: With dihydrogen peroxide; sodium acetate In water at 20 - 65℃; for 1h;	61%
With sodium hydroxide monohydrate at 6℃; for 4h; Temperature;

2-aminopropanediamide (62009-47-6) + 1-phenyl-propane-1,2-dione-1-phenylhydrazone (27913-51-5) → 4-methyl-5-phenyl-1H-imidazole-2-carboxamide

Conditions	Yield
for 72h; Heating;	77%

2-aminopropanediamide (62009-47-6) + ethyl 2-(3-fluoro-4-nitrobenzoyl)-3-(dimethylamino)acrylate (939807-29-1) → ethyl 5-(aminocarbonyl)-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate (939807-30-4)

Conditions	Yield
Stage #1: 2-aminopropanediamide; ethyl 2-(3-fluoro-4-nitrobenzoyl)-3-(dimethylamino)acrylate In acetic acid at 80℃; for 2h; Stage #2: With trifluoroacetic acid at 60℃; for 4h;	76%

2-aminopropanediamide (62009-47-6) + 1-phenylhydrazono-1-(4-pyridinyl)-2-propanone → 4-methyl-5-(4-pyridinyl)-1H-imidazole-2-carboxamide

Conditions	Yield
In various solvent(s) for 72h; Mechanism; Heating; other 1,2-diketone monophenylhydrazones;	74%
for 72h; Heating;	74%

ethyl iminoethoxycarbonylacetate hydrochloride + 2-aminopropanediamide (62009-47-6) → ethyl 4-carbamoyl-5-hydroxy-1H-imidazole-2-acetate

Conditions	Yield
In methanol	72.7%

2-aminopropanediamide (62009-47-6) + benzil phenylhydrazone (6630-86-0) → 4,5-diphenyl-1H-imidazole-2-carboxamide (41270-78-4)

Conditions	Yield
for 72h; Heating;	71%

Ethyl imino α-carbamoylacetate hydrochloride (72727-87-8) + 2-aminopropanediamide (62009-47-6) → 4-carbamoyl-5-hydroxy-1H-imidazole-2-acetamide

Conditions	Yield
In methanol	70.3%

ethyl 2-(3-fluoro-4-nitrobenzoyl)-3-(dimethylamino)acrylate + 2-aminopropanediamide (62009-47-6) → ethyl 5-(aminocarbonyl)-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate (939807-30-4)

Conditions	Yield
In acetic acid at 80℃;	69%

Glyoxal (131543-46-9) + 2-aminopropanediamide (62009-47-6) → 3-oxo-3,4-dihydropyrazine-2-carboxamide (55321-99-8)

Conditions	Yield
Stage #1: Glyoxal; 2-aminopropanediamide In water at 90℃; for 3h; Inert atmosphere; Stage #2: With ammonium hydroxide; dihydrogen peroxide In water at 20℃; for 1h; pH=7; Inert atmosphere;	63%

2-aminopropanediamide (62009-47-6) + dimethylglyoxal (431-03-8) → 5,6-dimethyl-3-oxo-3,4-dihydropyrazine-2-carboxamide (90000-71-8)

Conditions	Yield
With water; sodium hydroxide at 10℃; for 0.333333h;	51%
With sodium hydroxide
With acetic acid; sodium hydroxide In water at 10℃; for 2.33333h; pH=6;	13.00 g

2-aminopropanediamide (62009-47-6) + phenyl-glyoxal-2-phenylhydrazone (5335-28-4) → 4-phenyl-1H-imidazole-2-carboxamide (41270-75-1)

Conditions	Yield
for 72h; Heating;	51%

2-aminopropanediamide (62009-47-6) + biacetyl phenylhydrazone (13732-32-6) → 4,5-dimethyl-1H-imidazole-2-carboxamide

Conditions	Yield
for 72h; Heating;	46%

2-aminopropanediamide (62009-47-6) + 1-(phenylhydrazono)-propan-2-one (5391-74-2) → 4-methyl-1H-imidazole-2-carboxamide

Conditions	Yield
for 72h; Heating;	42%

2-aminopropanediamide (62009-47-6) + 2-oxopropanal (78-98-8) → 5-methyl-3-oxo-3,4-dihydropyrazine-2-carboxamide (88394-05-2)

Conditions	Yield
Stage #1: 2-oxopropanal With sodium hydrogensulfite; sodium hydroxide In water at 80℃; for 1h; Stage #2: 2-aminopropanediamide In water at 80℃; for 2h; Stage #3: With dihydrogen peroxide; sodium acetate In water at 20 - 65℃;	36%
With sodium hydroxide

2-aminopropanediamide (62009-47-6) + 2-oxopropanal (78-98-8) → 6-methyl-3-oxo-3,4-dihydro-pyrazine-2-carboxylic acid amide (88394-06-3)

Conditions	Yield
Stage #1: 2-aminopropanediamide; 2-oxopropanal With sodium hydroxide In water at -20 - 20℃; Stage #2: With hydrogenchloride In water at -20 - 20℃; for 48h;	28%

2-oxo-propionic acid ethyl ester (617-35-6) + 2-aminopropanediamide (62009-47-6) → 6-methyl-3,5-dioxo-2,3,4,5-tetrahydro-pyrazine-2-carboxylic acid amide

Conditions	Yield
With sodium methylate

dichloro-acetic acid (79-43-6) + 2-aminopropanediamide (62009-47-6) → (2,2-dichloro-acetylamino)-malonic acid diamide (98022-03-8)

formic acid (64-18-6) + 2-aminopropanediamide (62009-47-6) → formylamino-malonic acid diamide (10265-51-7)

Conditions	Yield
at 100℃;

formimidic acid ethyl ester (44234-35-7) + 2-aminopropanediamide (62009-47-6) → 5-oxo-4,5-dihydro-1H-imidazole-4-carboxylic acid amide (68543-34-0)

Conditions	Yield
With hydrogenchloride

N-acetyldithiocarbamic acid ethyl ester (6322-61-8) + 2-aminopropanediamide (62009-47-6) → (N'-acetyl-thioureido)-malonic acid diamide

Conditions	Yield
With ethanol

2-aminopropanediamide (62009-47-6) + phenylglyoxal hydrate (1074-12-0) → 3-oxo-6-phenyl-3,4-dihydro-pyrazine-2-carboxylic acid amide (67602-11-3)

Conditions	Yield
With sodium hydroxide

2-aminopropanediamide (62009-47-6) + O-ethyl N-benzoylthiocarbamidate (6958-78-7) → (O-ethyl-N'-benzoyl-isoureido)-malonic acid diamide

Conditions	Yield
With ethanol at 100℃;

Upstream product

• 69645-51-8 2-nitromalonamide 
• 14064-10-9 diethyl 2-chloromalonate 
• 7664-41-7 ammonia 
• 13433-00-6 diethyl aminomalonate hydrochloride 
• 6829-40-9 aminomalonic acid diethyl ester 

Downstream Products

• 55321-99-8 3-oxo-3,4-dihydropyrazine-2-carboxamide 
• 90000-71-8 5,6-dimethyl-3-oxo-3,4-dihydropyrazine-2-carboxamide 
• 41270-78-4 4,5-diphenyl-1H-imidazole-2-carboxamide 
• 939807-27-9 ethyl 5-(aminocarbonyl)-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate 
• 5181-05-5 2-aminomalononitrile 
• 88394-05-2 3-carboxamido-2-hydroxy-6-methylpyrazine 
• 428854-24-4 2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6- triamine 
• 1237524-82-1 3-hydroxy-2-carbamoylpyrazine sodium salt 
• 1131657-93-6 2-aminomalonamide benzenesulfonate 
• 56973-26-3 5-hydroxy-1H-imidazole-4-carboxamide 
• 939807-30-4 ethyl 5-(aminocarbonyl)-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate 
• 88394-06-3 2-Hydroxy-5-methyl-pyrazin-3-carbonsaeure-amid 
• 70180-49-3 2-(4-chloro-phenyl)-5-oxo-4,5-dihydro-1⁽³⁾H-imidazole-4-carboxylic acid amide 
• 70180-48-2 2-(4-fluoro-phenyl)-5-oxo-4,5-dihydro-1⁽³⁾H-imidazole-4-carboxylic acid amide 

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