198989-07-0

Basic information

• Product Name: 2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: N-BOC-2,5-DIAZA-BICYCLO[2.2.1]HEPTANE;2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER;2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID;2-(tert-Butyloxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane;2-Boc-2,5-diazabicyclo[2.2.1]heptane
• CAS NO: 198989-07-0
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 198.26
• Mol File: 198989-07-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 75-77°C
• Boiling Point: 276℃
• Flash Point: 121℃
• Appearance: /
• Density: 1.104
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.74±0.20(Predicted)
• CAS DataBase Reference: 2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER(198989-07-0)
• EPA Substance Registry System: 2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER(198989-07-0)

Safety Data

• Hazardous Substances Data: 198989-07-0(Hazardous Substances Data)

Usage

General Description

2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester is a chemical compound with a molecular formula of C9H17NO2. It is a tert-butyl ester derivative of 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid, which is a heterocyclic compound. This chemical is used as a building block in the synthesis of pharmaceuticals and agrochemicals. It has the potential to act as a ligand for metal catalysts and has been studied for its potential biological activities. Additionally, it is used as a reagent for the preparation of various other chemicals and compounds in organic synthesis.

Synthetic route

2,5-diazabicyclo[2.2.1]heptane dihydrobromide + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0)

Conditions	Yield
With triethylamine In methanol at -30 - 25℃;	200 mg

1'-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro-[cyclopropane-1,3'-indoline]-6'-carboxylic acid + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(1'-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1,3-indolin]-6'-ylcarbonyl)-2,5-diazabicyclo-[2.2.1]heptane-2-carboxylate

Conditions	Yield
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 23℃; for 16h;	96.5%

Ethyl 4-bromobenzoate (5798-75-4) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(4-(ethoxycarbonyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 24h;	92%

trifluoroacetic anhydride (407-25-0) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl-2-(trifluoroacetyl)-2,5-diazabicyclo[2.2.1]heptane-5-carboxylate

Conditions	Yield
With triethylamine at 0 - 20℃; for 2.5 - 3.5h;	87.2%

2-chloropyridine (109-09-1) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
With methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II); sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Sealed tube; Inert atmosphere;	87%

6-chloronicotinonitrile (33252-28-7) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(5-cyanopyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h;	85%

3-(5-bromo-2-pyrimidinyl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (651340-91-9) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
With potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 60℃;	84%

9-ethyl-6,6-dimethyl-8-iodo-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → C31H34N4O3

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium hexamethyldisilazane In tetrahydrofuran; 1,4-dioxane at 60℃; Inert atmosphere;	59%

7-chlorothiazolo[5,4-d]pyrimidin-5-amine (1211527-74-0) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(5-aminothiazolo[5,4-d]pyrimidin-7-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1435954-40-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 3h;	55.5%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 3h;	55.5%

4-Fluoronitrobenzene (350-46-9) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → 5-(4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (877212-94-7)

Conditions	Yield
In acetonitrile at 100℃;	52%
Stage #1: 4-Fluoronitrobenzene With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate In dimethyl sulfoxide at 70℃; for 5h;

[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (1188374-41-5) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → 5-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1232028-17-9)

Conditions	Yield
Stage #1: [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate In N,N-dimethyl-formamide at 20℃;	51%

3-bromo-6-chloro-imidazo[1,2-b]pyridazine (13526-66-4) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1400874-04-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 130℃; for 4h;	49%

4-{[(2S,4R)-2-methyl-1-propionyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}benzoic acid + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(4-{[(2S,4R)-2-methyl-1-propionyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}benzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	49%

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) + 2,3-dimethylbenzoic acid (603-79-2) → 5-(2,3-dimethylbenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 17h;	42%

2-Fluoro-4-(trifluoromethyl)benzaldehyde (89763-93-9) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → t-butyl 5-(2-formyl-5-(trifluoromethyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃;	34%

para-diiodobenzene (624-38-4) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → tert-butyl 5-(4-iodophenyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate (1197294-09-9)

Conditions	Yield
With potassium phosphate; copper(l) iodide; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide at 80 - 90℃;	33%

3-fluoro-2-methylbenzoic acid (699-90-1) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → 5-(3-fluoro-2-methylbenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 17h;	31.62%

2-(3-((7-(3-chloropropoxy)quinazolin-4-yl)amino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide (722544-46-9) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → 5-(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1H-pyrazol-3-yl)amino)quinazolin-7-yl)oxy)propyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 60℃;	29%

1-Bromo-2-chloroethane (107-04-0) + tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198989-07-0) → 5-(2-chloroethyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 17h;	24.71%

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 920531-56-2 5-[1-(2-chloro-phenyl)-ethyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 877212-94-7 5-(4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 1197294-09-9 tert-butyl 5-(4-iodophenyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate 
• 1426669-28-4 6-{4-[5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]phenyl}-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid 
• 769099-80-1 C₁₂H₁₅FN₂ 

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