302341-61-3

Basic information

• Product Name: tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate
• Synonyms: tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate;3-(BOC-AMINOMETHYL)-6-CYANOPYRIDINE;TERT-BUTYL ((6-CYANOPYRIDIN-3-YL)METHYL)CARBAMATE
• CAS NO: 302341-61-3
• Molecular Formula: C₁₂H₁₅N₃O₂
• Molecular Weight: 233.2664
• Mol File: 302341-61-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate(302341-61-3)
• EPA Substance Registry System: tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate(302341-61-3)

Safety Data

• Hazardous Substances Data: 302341-61-3(Hazardous Substances Data)

Upstream product

• 800412-55-9 tert-butyl[6-(aminocarbonyl)-3-pyridinyl]methylcarbamate 
• 67515-95-1 5-chlorocarbonyl-pyridine-2-carboxylic acid ethyl ester 
• 100-54-9 pyridine-3-carbonitrile 
• 65346-04-5 5-cyano-2-pyridinecarboxamide 
• 100-26-5 Pyridine-2,5-dicarboxylic acid 
• 17874-78-1 6-ethoxycarbonylpyridine-3-carboxylic acid 
• 41051-03-0 ethyl 5-cyano-2-pyridinecarboxylate 
• 557-21-1 dicyanozinc 
• 285119-72-4 (6-chloropyridin-3-ylmethyl)carbamic acid tert-butyl ester 
• 181130-13-2 5-(azidomethyl)pyridine-2-carbonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58553-48-3 5-(hydroxymethyl)pyridine-2-carbonitrile 
• 181130-14-3 5-(aminomethyl)pyridine-2-carbonitrile 
• 26218-78-0 methyl 6-bromonicotinate 

Downstream Products

• 182291-43-6 tert-butyl {(tert-butoxycarbonyl)[(1R)-2-[(2S)-2-({[(6-cyano-3-pyridinyl)methyl]amino}carbonyl)-2,5-dihydro-1H-pyrrol-1-yl]-1-(cyclohexylmethyl)-2-oxoethyl]amino}acetate 
• 182291-44-7 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-oxo-2-{2-[(6-thiocarbamoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-ethyl)-amino]-acetic acid tert-butyl ester 
• 788801-45-6 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-{2-[(6-methylsulfanylcarbonimidoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-2-oxo-ethyl)-amino]-acetic acid tert-butyl ester 
• 928649-09-6 tert-butyl N-[(6-hydroxymethyl-3-pyridyl)methyl]carbamate 
• 609345-79-1 5-(aminomethyl)pyridine-2-carboximidamide 

Relevant articles and documents

Improving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue

Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH2 sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-dLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors.

Technical scale synthesis of a new and highly potent thrombin inhibitor

In this account, we describe the development of an efficient and convergent process for the peptidomimetic thrombin inhibitor 1 on production plant scale. Starting from nicotinonitrile (13), (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2- pyrrolidinecarboxylic acid (5) and (2R)-2-amino-3-cyclohexylpropanoic acid (29) compound 1 was obtained in 16 chemical steps. New methods had been developed for the preparation of the key intermediate dehydroproline 22 and the transformation of nitriles into amidines. The thrombin inhibitor 1 was isolated by special techniques (nanofiltration and spray drying). Almost all salts of 1 are amorphous, however, a crystalline complex was obtained with 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Saccharin).

PHARMACEUTICAL COMBINATION

There is provided a combination product comprising: (1) a compound of claim 1 in WO 02/44145 or a compound of claim 20 in WO 02/44145 (or derivative thereof)or a pharmaceutically-acceptable derivative thereof; and (1) a compound as defined in claim 1 of WO 01/28992 or (2) a compound of Claim 34 of WO 01/28992 or (3) Compound A or B or C or D (or pharmaceutically-acceptable salts thereof) for use in treating arrhythmia or a coagulation controlled complication thereof.