[ CAS No. 1232410-49-9 ] {[proInfo.proName]}

Name: 1232410-49-9|3-Amino-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide|98+%
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SKU: A312952
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2D 3D

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Quality Control of [ 1232410-49-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1232410-49-9 ]

SDS Specification

Alternatived Products of [ 1232410-49-9 ]

Product Details of [ 1232410-49-9 ]

CAS No. :	1232410-49-9	MDL No. :	MFCD19443686
Formula :	C₁₈H₁₆N₄O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DUIHHZKTCSNTGM-UHFFFAOYSA-N
M.W :	368.41	Pubchem ID :	51000408
Synonyms :	ATR Inhibitor IV

Calculated chemistry of [ 1232410-49-9 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.06
Num. rotatable bonds :	5
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	99.18
TPSA :	123.42 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	2.05
Log Po/w (WLOGP) :	3.28
Log Po/w (MLOGP) :	1.08
Log Po/w (SILICOS-IT) :	1.68
Consensus Log Po/w :	1.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.6
Solubility :	0.093 mg/ml ; 0.000252 mol/l
Class :	Soluble
Log S (Ali) :	-4.27
Solubility :	0.0198 mg/ml ; 0.0000537 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.59
Solubility :	0.0000951 mg/ml ; 0.000000258 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.89

Safety of [ 1232410-49-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1232410-49-9 ]

* 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.

Upstream synthesis route of [ 1232410-49-9 ]
Downstream synthetic route of [ 1232410-49-9 ]

[ 1232410-49-9 ] Synthesis Path-Upstream 1~5

1
[ 1232423-29-8 ]
[ 62-53-3 ]
[ 1232410-49-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With diethyl cyanophosphonate; triethylamine In 1,2-dimethoxyethane at 120℃; for 18 h;	A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.1 14 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μL, 5.1 14 mmol), aniline (476.2 mg, 465.9 μL, 5.1 14 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) were stirred in DME (18.75 mL) at 120 °C for 18 hours. After this time water was added and the resultant solid collected by filtration. The solid was triturated with acetone and dried to give the desired product (1.335g, 71percent Yield). 1H NMR (400.0 MHz, DMSO) d 3.28 (s, 3H), 7.18 (t, J = 7.3 Hz, I H), 7.41 (t, J = 7.8 Hz, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.89 (s, 2H), 8.01 (d, J = 8.4 Hz, 2H), 8.51 (d, J = 8.4 Hz, 2H), 9.04 (s, 1H) andlψ.47 (s, I H) ppm; MS (ES⁺) 369
71%	With diethyl cyanophosphonate; triethylamine In 1,2-dimethoxyethane at 120℃; for 18 h;	Step 4: 3-Amino-6-(4-(methylsulfonyl)phenyl)-iV-phenylpyrazine-2-carboxamide[00144] A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.114 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μ, 5.114 mmol), aniline (476.2 mg, 465.9 μ, 5.114 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) was stirred in DME (18.75 mL) at 120 °C for 18 hours. After this time water was added and the resultant solid collected by filtration and triturated with acetone to give the desired product (1.88g, 71percent Yield). 3/4 NMR (400.0 MHz, DMSO) δ 10.47 (s, 1H), 9.04 (s, 1H), 8.51 (d, J = 8.4 Hz, 2H), 8.01 (d, J = 8.4 Hz, 2H), 7.89 (s, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.41 (t, J = 7.8 Hz, 2H), 7.18 (t, J = 7.3 Hz, 1H) and 3.28 (s, 3H) ppm; MS (ES⁺) 369.0.

Reference： [1] Patent: WO2010/71837, 2010, A1, . Location in patent: Page/Page column 176
[2] Patent: WO2011/143425, 2011, A2, . Location in patent: Page/Page column 37; 39

2
[ 16298-03-6 ]
[ 1232410-49-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2320 - 2330

3
[ 6966-01-4 ]
[ 1232410-49-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2320 - 2330

4
[ 486424-37-7 ]
[ 1232410-49-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2320 - 2330

5
[ 1232423-27-6 ]
[ 1232410-49-9 ]

Reference： [1] Patent: WO2011/143425, 2011, A2,

[ 1232410-49-9 ] Synthesis Path-Downstream 1~10

1
[ 1232423-29-8 ]
[ 62-53-3 ]
[ 1232410-49-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With diethyl cyanophosphonate; triethylamine; In 1,2-dimethoxyethane; at 120℃; for 18h;	A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.1 14 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 muL, 5.1 14 mmol), aniline (476.2 mg, 465.9 muL, 5.1 14 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) were stirred in DME (18.75 mL) at 120 C for 18 hours. After this time water was added and the resultant solid collected by filtration. The solid was triturated with acetone and dried to give the desired product (1.335g, 71% Yield). 1H NMR (400.0 MHz, DMSO) d 3.28 (s, 3H), 7.18 (t, J = 7.3 Hz, I H), 7.41 (t, J = 7.8 Hz, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.89 (s, 2H), 8.01 (d, J = 8.4 Hz, 2H), 8.51 (d, J = 8.4 Hz, 2H), 9.04 (s, 1H) andltheta.47 (s, I H) ppm; MS (ES+) 369
71%	With diethyl cyanophosphonate; triethylamine; In 1,2-dimethoxyethane; at 120℃; for 18h;	Step 4: 3-Amino-6-(4-(methylsulfonyl)phenyl)-iV-phenylpyrazine-2-carboxamide[00144] A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.114 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 mu, 5.114 mmol), aniline (476.2 mg, 465.9 mu, 5.114 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) was stirred in DME (18.75 mL) at 120 C for 18 hours. After this time water was added and the resultant solid collected by filtration and triturated with acetone to give the desired product (1.88g, 71% Yield). ¾ NMR (400.0 MHz, DMSO) delta 10.47 (s, 1H), 9.04 (s, 1H), 8.51 (d, J = 8.4 Hz, 2H), 8.01 (d, J = 8.4 Hz, 2H), 7.89 (s, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.41 (t, J = 7.8 Hz, 2H), 7.18 (t, J = 7.3 Hz, 1H) and 3.28 (s, 3H) ppm; MS (ES+) 369.0.

Reference： [1]Patent: WO2010/71837,2010,A1 .Location in patent: Page/Page column 176
[2]Patent: WO2011/143425,2011,A2 .Location in patent: Page/Page column 37; 39

2
[ 16298-03-6 ]
[ 1232410-49-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2320 - 2330

3
[ 6966-01-4 ]
[ 1232410-49-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2320 - 2330

4
[ 486424-37-7 ]
[ 1232410-49-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2320 - 2330

5
[ 36204-92-9 ]
4-(methylsulfonyl)phenyl boronic acid derivative [ No CAS ]
[ 1232410-49-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2320 - 2330

6
[ 1232410-49-9 ]
[ 1349198-24-8 ]

Yield	Reaction Conditions	Operation in experiment
48%		Step 5: 3-Hydroxy-6-(4-(methylsulfonyl)phenyl)-7V-phenylpyrazine-2-carboxamide[00145] A slurry of copper dibromide (151.6 mg, 0.6786 mmol) in DMF (1.125 mL) at 60C was treated with tert-butyl nitrite (139.9 mg, 161.4 mu, 1.357 mmol). A solution of 3- amino-6-(4-methylsulfonylphenyl)-N-phenyl-pyrazine-2-carboxamide (250 mg, 0.6786 mmol) in DMF (1.062 mL) was then added by dropwise addition and the mixture stirred for 1 hour at 60C for 48 hours. The reaction mixture was quenched into a precooled 10wt% HC1 (2.474 mL of 10 %w/v, 6.786 mmol) solution containing sulfamic acid (59.30 mg, 0.6107 mmol) and the resultant solid was isolated by filtration and washing with water (161mg, 48% Yield). ¾ NMR (400.0 MHz, DMSO) delta 3.26 (s, 3H), 7.16 (s, 1H), 7.38 (s, 2H), 7.74 - 7.77 (m, 2H), 8.02 - 8.06 (m, 3H) and 8.26 - 8.28 (m, 2H) ppm; MS (ES+) 369.95.

Reference： [1]Patent: WO2011/143425,2011,A2 .Location in patent: Page/Page column 37; 39-40

7
[ 1232410-49-9 ]
[ 1349198-25-9 ]

Reference： [1]Patent: WO2011/143425,2011,A2

8
[ 1232410-49-9 ]
[ 1349198-21-5 ]

Reference： [1]Patent: WO2011/143425,2011,A2

9
[ 1232423-27-6 ]
[ 1232410-49-9 ]

Reference： [1]Patent: WO2011/143425,2011,A2

10
[ 1232410-49-9 ]
6-(4-(methylsulfonyl)phenyl)-N-phenyl-3-(sulfamoylamino)pyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: A solution of <strong>[1232410-49-9]VE-821</strong> or <strong>[1232410-49-9]VE-822</strong> (0.54 mmol, 1.0 equiv.) and triethylamine (1.62 mmol, 3.0 equiv.) in 10 mL of methylene chloride was added to a mixture of chlorosulfonyl isocyanate (0.68 mmol, 1.2 equiv.) and tert-butanol (0.648 mmol, 1.2 equiv.) in 2 mL of methylene chloride. The mixture was stirred at room temperature for 1.0 h, diluted with ethyl acetate, and washed with water. The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by chromatography with a silica gel and methylene chloride methanol 98:2 as an eluent. This intermediate was thereafter diluted in a solution of trifluoro acetic acid in methylene chloride (20% vol.) and stirred at room temperature for 6 h. Next, the mixture was concentrated under vacuum and co-evaporated with diethyl ether multiple times to obtain the expected compound witha 58-65% yield.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 691 - 702

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P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P362	Take off contaminated clothing and wash before reuse.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H361d	Suspected of damaging the unborn child
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H370	Causes damage to organs
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1232410-49-9 ] {[proInfo.proName]}

Quality Control of [ 1232410-49-9 ]

Related Doc. of [ 1232410-49-9 ]

Product Details of [ 1232410-49-9 ]

Calculated chemistry of [ 1232410-49-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1232410-49-9 ]

Application In Synthesis of [ 1232410-49-9 ]

[ 1232410-49-9 ] Synthesis Path-Upstream 1~5

[ 1232410-49-9 ] Synthesis Path-Downstream 1~10

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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