16082-33-0

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Diamino-1H-pyrazole is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical sector, 3,5-Diamino-1H-pyrazole is utilized as a key intermediate, playing a crucial role in the production of agrochemicals that aid in crop protection and enhancement.
Used in Dye and Pigment Production:
3,5-Diamino-1H-pyrazole is used as a building block in the production of dyes and pigments, enabling the creation of a wide range of colors for various applications.
Used in Specialty Chemicals:
3,5-Diamino-1H-pyrazole is also employed in the synthesis of specialty chemicals, where its unique properties can be harnessed for specific industrial applications.

InChI:InChI=1/C3H6N4/c4-2-1-3(5)7-6-2/h1H,(H5,4,5,6,7)

Synthetic route

malononitrile (109-77-3) → 1H-pyrazole-3,5-diamine (16082-33-0)

Conditions	Yield
With ethanol; hydrazine hydrate

3.5-bis-ethoxycarbonylimino-pyrazolidine → 1H-pyrazole-3,5-diamine (16082-33-0)

Conditions	Yield
With barium dihydroxide

Malondiimidsaeure-diethylester (26315-24-2) → 1H-pyrazole-3,5-diamine (16082-33-0)

Conditions	Yield
With hydrazine In ethanol at 4℃; for 16.1667h;
Stage #1: Malondiimidsaeure-diethylester With potassium carbonate In diethyl ether at 0℃; Saturated solution; Stage #2: With hydrazine hydrate In ethanol Reflux;

1H-pyrazole-3,5-diamine (16082-33-0) + (E)-2-Benzoyl-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile → 2-Benzoyl-3-(3,4,5-trimethoxyphenyl)-3-(3,5-diaminopyrazol-4-yl)propionitril

Conditions	Yield
In ethanol at 40℃; for 0.333333h;	87%

1H-pyrazole-3,5-diamine (16082-33-0) + Ethyl 3-ethoxy-3-iminopropionate (27317-59-5) → 2,5-Diamino-pyrazolo<1,5-a>pyrimidin-7(4H)-on

Conditions	Yield
In ethanol Heating;	58.1%

1H-pyrazole-3,5-diamine (16082-33-0) + ethyl 3-oxo-3-phenylpropionate (94-02-0) + acetic acid (64-19-7) → C14H12N4O2 (934293-50-2)

Conditions	Yield
for 5h; Heating / reflux;	35%

1H-pyrazole-3,5-diamine (16082-33-0) + (4aS,6aS,6bR,13aR)-12-amino-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4-a-carbonyl chloride → (4aS,6aS,6bR,13aR)-12-amino-N-(3-amino-1H-pyrazol-5-yl)-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4-a-carboxamide

Conditions	Yield
In pyridine at 20℃;	25%

1H-pyrazole-3,5-diamine (16082-33-0) + (4aS,6aS,6bR,13aR)-12-amino-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4a-carbonyl chloride (1415383-28-6) → (4aS,6aS,6bR,13aR)-12-amino-N-(3-amino-1H-pyrazol-5-yl)-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4a-carboxamide (1415382-84-1)

Conditions	Yield
With pyridine In pyridine at 20℃;	25%

1H-pyrazole-3,5-diamine (16082-33-0) + potassium cyanate (590-28-3) → N,N''-(1H-pyrazole-3,5-diyl)-di-urea

Conditions	Yield
With hydrogenchloride

1H-pyrazole-3,5-diamine (16082-33-0) + benzoyl chloride (98-88-4) → N,N'-(1H-pyrazole-3,5-diyl)-bis-benzamide

Conditions	Yield
With sodium hydroxide

1H-pyrazole-3,5-diamine (16082-33-0) → 3,5-diamino-4-iodopyrazole

Conditions	Yield
With bis(pyridine)iodonium(I)tetrafluoroborate In dimethyl sulfoxide for 5h; Ambient temperature;

4-methyl-8-(morpholin-4-ylsulfonyl)-furo[3,4-c]quinoline-1,3-dione (753482-69-8) + 1H-pyrazole-3,5-diamine (16082-33-0) → 2-(5-amino-1H-pyrazol-3-yl)-4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-dione

Conditions	Yield
Stage #1: 4-methyl-8-(morpholin-4-ylsulfonyl)-furo[3,4-c]quinoline-1,3-dione; 1H-pyrazole-3,5-diamine With pyridine at 20℃; for 0.5h; Stage #2: With acetic anhydride for 3h; Heating;

1H-pyrazole-3,5-diamine (16082-33-0) + trifluoroacetic anhydride (407-25-0) → N-(5-amino-1H-pyrazol-3-yl)-2,2,2-trifluoro-acetamide (452913-45-0)

1H-pyrazole-3,5-diamine (16082-33-0) + 5-(2,3-difluoro-phenyl)-3-oxo-pentanoic acid ethyl ester (412950-62-0) + acetic acid (64-19-7) → N-{5-[2-(2,3-difluoro-phenyl)-ethyl]-7-hydroxy-pyrazolo[1,5-a]pyrimidin-2-yl}acetamide (1185908-04-6)

Conditions	Yield
at 100℃; for 18h;

1H-pyrazole-3,5-diamine (16082-33-0) + sodium (1,3-dioxopropan-2-ylidyne)azinate monohydrate → 5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine

Conditions	Yield
With acetic acid at 90℃; for 6h; Sealed tube;	0.91 g

1H-pyrazole-3,5-diamine (16082-33-0) + 1,3-dimethyluracil (874-14-6) → 2-amino-4H,5H-pyrazolo[1,5-a]pyrimidin-5-one

Conditions	Yield
With sodium ethanolate In ethanol at 80℃; for 15h;

1H-pyrazole-3,5-diamine (16082-33-0) + 1,3-dimethyluracil (874-14-6) → 2-aminopyrazolo[1,5-a]pyrimidin-5-ol

Conditions	Yield
With sodium ethanolate In ethanol at 80℃;

Upstream product

• 26315-24-2 Malondiimidsaeure-diethylester 
• 109-77-3 malononitrile 

Downstream Products

• 934293-50-2 C₁₄H₁₂N₄O₂ 
• 1185908-04-6 N-{5-[2-(2,3-difluoro-phenyl)-ethyl]-7-hydroxy-pyrazolo[1,5-a]pyrimidin-2-yl}acetamide 
• 1186608-97-8 5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine 

Relevant academic research and scientific papers

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The invention described herein relates to certain bicyclic heteroaromatic N-substituted glycine derivatives of formula (I) which are antagonists of HIF prolyl hydroxylases and are useful for treating diseases benefiting from the inhibition of this enzyme, anemia being one example.

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF CXCR2

The present invention relates to compounds of formula (I) wherein R1, R2, X, Y and Z are as defined in the specification.