398491-59-3

Basic information

• Product Name: 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE
• Synonyms: 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE;TERT-BUTYL 3-AMINO-4,6-DIHYDROPYRROLO[3,4-C]PYRAZOLE-5(1H)-CARBOXYLATE;5-BOC-3-AMINO-4,6-DIHYDRO-PYRROLO[3,4-C]PYROZOLE;tert-butyl 3-aminopyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate;3-Amino-5-Boc-pyrrolo[3,4-c]pyrazole;tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-C]pyrozole-5-carboxylate;5-Boc-3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole;3-Amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester
• CAS NO: 398491-59-3
• Molecular Formula: C₁₀H₁₆N₄O₂
• Molecular Weight: 224.26
• Product Categories: CHIRAL CHEMICALS
• Mol File: 398491-59-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 167-169 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 433.038 °C at 760 mmHg
• Flash Point: 215.694 °C
• Appearance: /
• Density: 1.315 g/cm³
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 16.32±0.20(Predicted)
• CAS DataBase Reference: 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE(398491-59-3)
• EPA Substance Registry System: 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE(398491-59-3)

Safety Data

• Hazardous Substances Data: 398491-59-3(Hazardous Substances Data)

Usage

General Description

5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE is a chemical compound with the molecular formula C16H20N4O2. It is a pyrrolopyrazole derivative and is often used in the synthesis of pharmaceuticals and agrochemicals. 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE is notable for its BOC (tert-butyloxycarbonyl) protected amine group, which makes it useful in organic synthesis for protecting other functional groups while reactions are carried out. The compound is also known for its potential interactions with biological targets, making it a subject of interest in medicinal and pharmaceutical research. Overall, 5N-BOC-3-AMINO-4,6-DIHYDRO-1H-PYRROLO[3,4-C]PYROZOLE is a versatile chemical with potential applications in various fields.

InChI:InChI=1/C10H18N4O2/c1-10(2,3)16-9(15)14-4-6-7(5-14)12-13-8(6)11/h6-7,12H,4-5H2,1-3H3,(H2,11,13)

Upstream product

• 175463-32-8 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 266353-19-9 [tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester 
• 3088-42-4 N-(2-cyanoethyl)glycine 
• 44915-39-1 [(2-cyanoethyl)amino]acetic acid methyl ester 
• 14011-37-1 hydrazine dihydrochloride 
• 266353-18-8 N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester 
• 44981-94-4 N-cyanoethyl glycine ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 398495-65-3 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester 
• 761443-69-0 5-tert-butyl 1-ethyl 3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate 
• 916995-51-2 danusertib 
• 916995-51-2 PHA₇₃₉₃₅₈ 
• 827318-78-5 5-((R)-2-methoxy-2-phenylacetyl)-3-[4-(4-methylpiperazin-1-yl)benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 916995-48-7 5-(methoxy-phenyl-acetyl)-3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 916995-45-4 5-(fluoro-phenyl-acetyl)-3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 916995-46-5 3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5-(2-phenyl-propionyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 916995-47-6 3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5-(2-phenyl-propionyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 827318-96-7 5-[(2R)-2-hydroxy-2-phenylethanoyl]-3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate 

Relevant articles and documents

Dipeptidyl peptidase-IV inhibitor-aminotetrahydropyrane derivative

The invention provides a DPPIV inhibitor which has the structure shown as the formula (I) (please see the formula (I) in the description). Experiments show that the inhibitor can effectively inhibit the activity of dipeptidyl peptidase IV (DPPIV) and be used for preventing DPPIV-mediated diseases or delaying progress of the DPPIV-mediated diseases or treating the DPPIV-mediated diseases, particularly 2 type and 1 type diabetes, obesity, arthritis, osteoporosis and part of tumors. The invention further provides a preparation method of the inhibitor.

(R)- N - [5 - (2 - methoxy - 2 - phenyl-acetyl) - 1, 4, 5, 6 - tetrahydro-pyrrolo [3, 4 - c] pyrazole - 3 - yl] - 4 - (4 - methyl piperazine - 1 - yl) benzamide synthesis method

The invention belongs to the technical field of medicine and relates to a preparation method for PHA739358(Danusertib), i.e., (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide. According to the invention, altogether four reaction routes are designed, simple and easily available glycine is used as a raw material, reactions like addition, esterification, amino protection and cyclization are carried out so as to prepare (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide, yield of the route 1, 2 and 4 is more than 25%, respectively, and yield of the route 3 is more than 20%. The preparation method has the advantages of a few reaction steps, simple and convenient post-treatment operation, little time consumption, high yield and low total cost. Thus, a novel method is provided for preparation of the antitumor drug PHA739358.

Structure-activity-relationship of amide and sulfonamide analogs of omarigliptin

A series of novel substituted-[(3R)-amino-2-(2,5-difluorophenyl)]tetrahydro-2H-pyran analogs have been prepared and evaluated as potent, selective and orally active DPP-4 inhibitors. These efforts lead to the discovery of a long acting DPP-4 inhibitor, omarigliptin (MK-3102), which recently completed phase III clinical development and has been approved in Japan.