Preparation and application of 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride_Industrial additives

Preparation and application background and overview of 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride

4,5,6,7-Tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride is also called 4,5,6,7-tetrahydro-1H-imidazo[4,5 -c]pyridine, which can be obtained by ring closure of histamine dihydrochloride and paraformaldehyde. There are reports in the literature that it can be used to prepare factor Xa inhibitors and CDK inhibitors.

Preparation and application of 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride

Dissolve histamine dihydrochloride (3.68g; 20mmol; 1eq) and paraformaldehyde (1.20g; 40mmol; 2eq) in water (30ml). The mixture was heated to reflux for 4 hours. The volatiles were evaporated and the residue was dried under vacuum. The compound was used without further purification. Yield: quantitative; ESI-MS m/z: 124,1[M+H]+; HPLC (Gradient C): rt 1,25min (100%), ¹H-NMR, MHz, DMSO d6: δ2.95-2.98,3.42(t,2H,3J＝5.9Hz),4.28(s,2H),9.02(s,1H),10.13(br s,2H),14.83(br s,1H bias Lithium borate).

Preparation and application of 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride

Preparation and application of 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride Application 1.

4,5,6,7-Tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride can be used to prepare Factor Xa inhibitors with the following structure. Factor Xa is a member of the trypsin-like serine protease enzyme family. It is a key enzyme in the coagulation cascade. The one-to-one binding of factors Xa and Va to calcium ions and phospholipids converts prothrombin into thrombin. Thrombin plays an important role in the blood coagulation mechanism by converting soluble plasma proteins and fibrinogen into insoluble fibrin.

Preparation and application of 4,5,6,7-tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride Application 2.

4,5,6,7-Tetrahydro-3H-imidazo[4,5-C]pyridine hydrochloride can be used to prepare CDK inhibitors with the following structure. Cyclin-dependent kinase (CDK) belongs to the serine/threonine protein kinase family and is a key kinase involved in cell cycle regulation. It has been reported that 20 different CDKs combine with cyclins to form active heterodimers and participate in physiological processes such as transcription, metabolism, neural differentiation and development.

References

[1] [Invented in China] CN201780081990.8 Bacterial glutamine cyclase and its inhibitor for treating periodontitis

[2] From PCT Int. Appl., 2004054, 0 phenylboric acid 8 Jul 2004

[3] From PCT Int. Appl., 2020224568, 12 Nov 2020