1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Hydrochloride Chemical Properties

Melting point:

247-249oC

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White

InChI

InChI=1S/C14H12FN5.ClH/c15-11-6-2-1-4-9(11)8-20-14-10(5-3-7-18-14)12(19-20)13(16)17;/h1-7H,8H2,(H3,16,17);1H

InChIKey

DQASIYVADJWVLY-UHFFFAOYSA-N

SMILES

C(C1C=CC=CC=1F)N1N=C(C(N)=N)C2C=CC=NC1=2.Cl

1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Hydrochloride Usage And Synthesis

Uses

1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Hydrochloride is a key intermediate in the synthesis of Riociguat, a potent, oral stimulator of soluble guanylate cyclase for the treatment of pulmonary hypertension.

Synthesis

In a 10 L four-necked flask, 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile 919.7 g (3.646 mol, 10 eq), MeOH 7 L was added, and MeONa 295 g (5.469 mol, 1.5 eq) was added with stirring, and stirred at room temperature for 2 h. Has disappeared, completely converted to the intermediate (7), added CH 3 C0 2 H 329 g (5.469 mol, 1.5 eq), NH 4 C1 293 g (5.469 mol, 1.5 eq), heated to reflux overnight, TLC monitoring reaction completely The temperature was lowered, a large amount of solid was precipitated, filtered, and washed with DCM to give 981 g of white solid as 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide (8), which was used directly in the next step. The compound 8 981.0 g (3.646 mol, lO eq) was added to 5 L of methyl tert-butyl ether, stirred, suspended as a suspension, passed through HC1 gas for about 2.5 h, filtered, washed with DCM, and dried by filtration. 1103.7 g of white solid 1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Hydrochloride. Total yield in two steps: 99.0%. Purity: 99%.

1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide Hydrochloride(256499-19-1)Related Product Information

• BENZENEAZOMALONONITRILE
• 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile
• methyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b] pyridin-3-yl)pyrimidin-5-yl)(ethyl)carbamate
• 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dimethyl-7,9-dihydro-8H-purin-8-one
• 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid
• 1-(3-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide
• 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dihydro-8H-purin-8-one
• 2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-N5,N5- dimethylpyrimidine-4,5,6-triamine
• isopropyl(4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b] pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate
• 1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxaMide
• 6-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl) -7-methyl-7,9-dihydro-8H-purin-8-one
• Riociguat
• 4,6-PyriMidinediaMine, 2-[1-[(2-fluorophenyl)Methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-(phenylazo)-
• 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyriMidine-4,5,6-triaMine
• Methyl [4,6-diaMino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyriMidin-5-yl]carbaMate