[ CAS No. 264600-78-4 ] {[proInfo.proName]}

Name: 264600-78-4|tert-Butyl pyrazin-2-ylcarbamate|95%
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SKU: A104633
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3d Animation Molecule Structure of 264600-78-4

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Quality Control of [ 264600-78-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 264600-78-4 ]

SDS Specification

Alternatived Products of [ 264600-78-4 ]

Product Details of [ 264600-78-4 ]

CAS No. :	264600-78-4	MDL No. :	MFCD16629882
Formula :	C₉H₁₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NAYPUKQOQAIRMP-UHFFFAOYSA-N
M.W :	195.22	Pubchem ID :	21992941
Synonyms :

Calculated chemistry of [ 264600-78-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.44
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.28
TPSA :	64.11 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	1.36
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	0.11
Log Po/w (SILICOS-IT) :	0.61
Consensus Log Po/w :	1.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	2.14 mg/ml ; 0.011 mol/l
Class :	Very soluble
Log S (Ali) :	-2.31
Solubility :	0.959 mg/ml ; 0.00491 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.61
Solubility :	0.483 mg/ml ; 0.00247 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.55

Safety of [ 264600-78-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 264600-78-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 264600-78-4 ]

[ 264600-78-4 ] Synthesis Path-Downstream 1~6

1
[ 768-66-1 ]
[ 264600-78-4 ]
[ 67-64-1 ]
[ 614732-04-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; water; ethyl acetate	260 2-Amino-3-[4-(2-fluorophenoxymethyl)piperidinolmethyl-pyrazine Example 260 2-Amino-3-[4-(2-fluorophenoxymethyl)piperidinolmethyl-pyrazine After adding 4 ml of n-butyllithium (2.46 M, n-hexane solution)to a solution of 1.384 g of 2,2,6,6-tetramethylpiperidine in tetrahydrofuran (15 ml) at -20° C. under a. nitrogen atmosphere, the mixture was stirred for 30 minutes while cooling on ice. The reaction mixture was cooled to -70° C., and then a solution of 800 mg of 2-(tert-butoxycarbonylamino)pyrazine in tetrahydrofuran (3 ml) was added dropwise, the mixture was stirred for 1 hour, 3 ml of N,N-dimethylformaldehyde was added, and stirring was continued for 30 minutes. After removing the cooling bath and stirring for 30 minutes, water was added and extraction was performed with ethyl acetate. The extract was dried and concentrated and then purified by silica gel column chromatography (solvent: ethyl acetate/n-hexane)to obtain 72 mg of crude 2-(tert-butoxycarbonylamino)pyrazine-3-carboxaldehyde.

Reference： [1]Current Patent Assignee: EISAI CO LTD - US2004/167224, 2004, A1

2
[ 264600-78-4 ]
[ 106-96-7 ]
[ 1448263-45-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;

Reference： [1]Chioua, Mourad; Soriano, Elena; Infantes, Lourdes; Jimeno, M. Luisa; Marco-Contelles, Jose; Samadi, Abdelouahid [European Journal of Organic Chemistry, 2013, # 1, p. 35 - 39]

3
[ 5049-61-6 ]
[ 24424-99-5 ]
[ 264600-78-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 2-Aminopyrazine; di-<i>tert</i>-butyl dicarbonate With dmap In tetrahydrofuran for 2h; Inert atmosphere; Stage #2: With triethylamine In tetrahydrofuran for 2h; Inert atmosphere; Stage #3: With sodium hydroxide In methanol at 20℃; for 2h;	GO (1544) 3-[(Pyrazin-2-yl)({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2- yl}methyl)amino]pyrazine-2-carboxamide To a stirred solution of pyrazin-2-amine (1 .902 g, 20 mmol) in THF (10 ml_) at rt under an argon atmosphere, was added DMAP (catalytic amount) followed by (B0C)20 (1 M solution in THF, 22 ml_, 22 mmol) dropwise. The reaction mixture was stirred for 2 h and then Et3N (2.024 g, 20 mmol) was added. After 1 h (BOC)20 (1 M solution in THF, 5 ml_, 5 mmol) was added dropwise and the reaction mixture stirred for a further 1 h. The reaction mixture was poured into 10% HCI solution (30 ml_) and extracted with CH2CI2 (30 ml_) twice. The combined organic fractions were dried over MgS04, filtered and the solvent removed by evaporation in vacuo. The crude product was dissolved in MeOH (30 ml_) and 1 M NaOH solution (20 ml_, 20 mmol) added. The reaction mixture was stirred for 2 h at rt and then neutralised using solid C02. Water (50 ml_) was added and the product extracted with CH2CI2 (50 ml_) twice. The combined organic fractions were dried over MgS04, filtered and the solvent removed by evaporation in vacuo. The product was dissolved in hexane/CH2CI2 treated with activated charcoal, filtered and the solvent removed by evaporation in vacuo to yield intermediate 1 as a white solid (3.18 g, 84%). (1547) 1H NMR (300 MHz, DMSO-cf6) d: 10.20 (br s, 1 H), 9.10 (d, J=1.5 Hz, 1 H), 8.36 (dd, J=2.5, 1.6 Hz, 1 H), 8.32 (d, J=2.6 Hz, 1 H), 1.54 (s, 9H).
67%	In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;

Reference： [1]Current Patent Assignee: KARUS THERAPEUTICS LIMITED - WO2019/166824, 2019, A1 Location in patent: Page/Page column 191; 192
[2]Régnier, Sophie; Bechara, William S.; Charette, André B. [Journal of Organic Chemistry, 2016, vol. 81, # 21, p. 10348 - 10356]

4
[ 264600-78-4 ]
C₁₆H₂₄N₄O₂⁽²⁺⁾*2CF₃O₃S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: 2-methoxypyridine / dichloromethane / 0.5 h / -78 - 20 °C / Inert atmosphere

Reference： [1]Régnier, Sophie; Bechara, William S.; Charette, André B. [Journal of Organic Chemistry, 2016, vol. 81, # 21, p. 10348 - 10356]

5
[ 618-42-8 ]
[ 264600-78-4 ]
tert-butyl (2-oxo-2-(piperidin-1-yl)ethyl)(pyrazin-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: tert-butyl pyrazin-2-ylcarbamate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-piperidin-1-yl-ethanone In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;

Reference： [1]Régnier, Sophie; Bechara, William S.; Charette, André B. [Journal of Organic Chemistry, 2016, vol. 81, # 21, p. 10348 - 10356]

6
[ 264600-78-4 ]
[ 134135-41-4 ]
C₁₅H₁₆N₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		To a stirred solution of intermediate 1 (0.975 g, 5 mmol) in DMF (20 ml_) under an argon atmosphere at rt was added NaH (60% dispersion in oil, 0.22 g, 5.5 mmol) in a single portion. The reaction mixture was stirred for 30 min and the cooled to 0C. <strong>[134135-41-4]5-(Bromomethyl)thiophene-2-carbonitrile</strong> (1.01 g, 5 mmol) was added as a solution in DMF (5 ml_). The reaction mixture was allowed to warm to rt and then stirred for a further 1 h before being poured into Na2C03 solution (20 ml_) and extracted with CH2CI2 (20 ml_) twice. The combined organic fractions were dried over MgS04, filtered and the solvent removed by evaporation in vacuo. Purification by silica gel column chromatography, 5% EtOAc/CH2CI2 elution, yielded intermediate 2 (1.236 g, 78%). (1549) LCMS (ESI): Found 317.0 [M+Hf.

Reference： [1]Patent: WO2019/166824,2019,A1 .Location in patent: Page/Page column 191; 192

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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acyl Group Substitution • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complex Metal Hydride Reductions • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Enamine Formation • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitrosation of Amines • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Synthesis of 2-Amino Nitriles • Ugi Reaction

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[ 264600-78-4 ]

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[ CAS No. 264600-78-4 ] {[proInfo.proName]}

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Calculated chemistry of [ 264600-78-4 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 264600-78-4 ]

Application In Synthesis of [ 264600-78-4 ]

[ 264600-78-4 ] Synthesis Path-Downstream 1~6

Technical Information

Related Functional Groups of [ 264600-78-4 ]

Amides

Amines

Related Parent Nucleus of [ 264600-78-4 ]

Pyrazines

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[ 264600-78-4 ]

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[ 264600-78-4 ]