[ CAS No. 1224944-51-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 1224944-51-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1224944-51-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1224944-51-7 ]

SDS Specification

Alternatived Products of [ 1224944-51-7 ]

Product Details of [ 1224944-51-7 ]

CAS No. :	1224944-51-7	MDL No. :	MFCD22551533
Formula :	C₈H₆ClN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FDJUGKZMZUVEJD-UHFFFAOYSA-N
M.W :	211.61	Pubchem ID :	58063364
Synonyms :

Calculated chemistry of [ 1224944-51-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.28
TPSA :	56.49 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	1.14
Log Po/w (WLOGP) :	1.17
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.9
Consensus Log Po/w :	1.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.21
Solubility :	1.29 mg/ml ; 0.00611 mol/l
Class :	Soluble
Log S (Ali) :	-1.92
Solubility :	2.54 mg/ml ; 0.012 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.41
Solubility :	0.818 mg/ml ; 0.00386 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.97

Safety of [ 1224944-51-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1224944-51-7 ]

* 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 [ 1224944-51-7 ]

[ 1224944-51-7 ] Synthesis Path-Downstream 1~13

1
[ 100-82-3 ]
[ 1224944-51-7 ]
[ 1224939-90-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In ethanol; for 4h;Reflux; Inert atmosphere;	A solution of methyl 5-chloropyrazolo[l,5-alpha]pyrimidine-3-carboxylate (240 mg, 1.1 mM, 1.0 equiv), 3-fluorobenzylamine (200 uL, 2.0 mM, 2.0 equiv), 30 mL of ethanol and 400 uL of N,N-diisopropylethylamine (2.0 mM, 2 equiv) were combined and heated under reflux for 4 hours. The mixture was concentrated and the product collected by filtration and washed with cold ethanol to give 271 mg (80%) of methyl 5-(3- fluorobenzylamino)pyrazolo[l,5-alpha]pyrimidine-3-carboxylate LCMS (ESI) m+H = 301.2, 1H NMR (400 MHz, OMSO-d6) delta: 8.56 (d, 1 H), 8.41 (m 1 H), 8.17 (s, 1 H), 7.35 (m, 3 H), 7.08 (td, 1 H), 6.44 (d, 1 H), 4.61 (d, 2 H), 3.74 (s, 3 H).
80%	With N-ethyl-N,N-diisopropylamine; In ethanol; for 4h;Reflux; Inert atmosphere;	A solution of <strong>[1224944-51-7]methyl 5-chloropyrazolo[1,5-c]pyrimidine-3-carboxylate</strong> (240 mg, 1.1 mM, 1.0 equiv), 3-fluorobenzylamine (200 uL, 2.0 mM, 2.0 equiv), 30 mL of ethanol and 400 uL of N,N-diisopropylethylamine (2.0 mM, 2 equiv) were combined and heated under reflux for 4 hours. The mixture was concentrated and the product collected by filtration and washed with cold ethanol to give 271 mg (80%) of methyl 5-(3-fluorobenzylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate LCMS (ESI) m+H=301.2, 1H NMR (400 MHz, DMSO-d6) delta: 8.56 (d, 1H), 8.41 (m 1H), 8.17 (s, 1H), 7.35 (m, 3H), 7.08 (td, 1H), 6.44 (d, 1H), 4.61 (d, 2H), 3.74 (s, 3H).

Reference： [1]Patent: WO2010/51549,2010,A1 .Location in patent: Page/Page column 81-82
[2]Patent: US2012/22043,2012,A1 .Location in patent: Page/Page column 35

2
[ 67-56-1 ]
[ 1224944-47-1 ]
[ 1224944-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	for 0.5h;Inert atmosphere;	A mixture of 5-oxo-4,5-dihydropyrazolo[l,5-alpha]pyrimidine-3-carboxylic acid (151 mg, 0.84 mM, 1.0 equiv), phosphorus oxychloride (20 mL) and N,N- diisopropylethylamine (440 uL, 2.5 mM, 3.0 equiv), were heated under reflux for 2 hours. The reaction mixture was cooled to ambient temperature overnight then concentrated under reduced pressure. The residue was dissolved in 20 mL of methanol, stirred for 30 minutes and concentrated under vacuum. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered through a pad of silica gel and concentrated to give 160 mg (90%) of methyl 5-chloropyrazolo[l,5- alpha]pyrimidine-3-carboxylate LCMS (ESI) m+H = 212.2, 1H NMR (400 MHz, DMSO-^) delta: 9.34 (d, 1 H), 8.68 (s, 1 H), 7.42 (d, 1 H), 3.83 (s, 3 H).

Reference： [1]Patent: WO2010/51549,2010,A1 .Location in patent: Page/Page column 81

3
[ 67-56-1 ]
[ 1224944-46-0 ]
[ 1224944-51-7 ]

Yield	Reaction Conditions	Operation in experiment
90%		A mixture of 5-oxo-4,5-dihydropyrazolo[1,5-c]pyrimidine-3-carboxylic acid (151 mg, 0.84 mM, 1.0 equiv), phosphorus oxychloride (20 mL) and N,N-diisopropylethylamine (440 uL, 2.5 mM, 3.0 equiv), were heated under reflux for 2 hours. The reaction mixture was cooled to ambient temperature overnight then concentrated under reduced pressure. The residue was dissolved in 20 mL of methanol, stirred for 30 minutes and concentrated under vacuum. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered through a pad of silica gel and concentrated to give 160 mg (90%) of methyl 5-chloropyrazolo[1,5-c]pyrimidine-3-carboxylate LCMS (ESI) m+H=212.2, 1H NMR (400 MHz, DMSO-d6) delta: 9.34 (d, 1H), 8.68 (s, 1H), 7.42 (d, 1H), 3.83 (s, 3H).

Reference： [1]Patent: US2012/22043,2012,A1 .Location in patent: Page/Page column 35

4
[ 29274-22-4 ]
[ 1224944-51-7 ]

Reference： [1]Patent: US2012/22043,2012,A1

5
[ 1224944-44-8 ]
[ 1224944-51-7 ]

Reference： [1]Patent: US2012/22043,2012,A1

6
[ 1224944-45-9 ]
[ 1224944-51-7 ]

Reference： [1]Patent: US2012/22043,2012,A1

7
[ 1224944-43-7 ]
[ 1224944-51-7 ]

Reference： [1]Patent: US2012/22043,2012,A1

8
[ 1224944-51-7 ]
[ 365996-30-1 ]
methyl 5-[[(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl]amino]pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	at 90.0℃; for 0.5h;Sealed tube; Microwave irradiation;	A microwave vial was charged with <strong>[1224944-51-7]methyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate</strong> (500 mg, 2.36 mmol), tert-butyl N-[(1S,2R)-2-aminocyclohexyl]carbamate (506 mg, 2.36 mmol), and methanol (4.7 mL). The vial was sealed and stirred at 90 C for 30 min in the microwave, resulting in a suspension. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography (0-100% isopropyl acetate/heptane) to afford methyl 5- [[(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl]amino]pyrazolo[1,5-a]pyrimidine-3- carboxylate (420.2 mg, 1.08 mmol, 46% yield) as a white solid. MS: m/z = 390 (M+1).

Reference： [1]Patent: WO2017/108723,2017,A2 .Location in patent: Page/Page column 708; 709

9
[ 1224944-51-7 ]
[ 365996-30-1 ]
5-(((1R,2S)-2-((tert-butoxycarbonyl)amino)cyclohexyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/108723,2017,A2

10
[ 29274-22-4 ]
[ 1224944-51-7 ]

Reference： [1]Patent: CN106336413,2017,A

11
3-iodopyrazolo[1,5-a]pyrimidine-5-ol [ No CAS ]
[ 1224944-51-7 ]

Reference： [1]Patent: CN106336413,2017,A

12
5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester [ No CAS ]
[ 1224944-51-7 ]

Yield	Reaction Conditions	Operation in experiment
61.9%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; for 2h;	5-hydroxypyrazole [1,5-a] pyrimidine-3-carboxylate (0.028 g, 0.14 mmol)Phosphorus oxychloride (0.8 mL, 8 mmol) andN, N-diisopropylethylamine (0.01 mL, 0.06 mmol)In a toluene (2 mL) solution for 2 h.Cooling to room temperature, removing phosphorus oxychloride under reduced pressure,The residue was quenched with warm water (35 mL), extracted with dichloromethane (35 mL x 3), dried over anhydrous sodium sulfate, concentrated under reduced pressure,Column separation (dichloromethane / methanol (v / v) = 80/1) gave 19 mg of a white solid in 61.9% yield.

Reference： [1]Patent: CN106336413,2017,A .Location in patent: Paragraph 0811; 0812; 0813

13
[ 22987-10-6 ]
[ 1224944-51-7 ]
methyl 5-((3-propionamidophenyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.59%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110.0℃; for 6h;Inert atmosphere;	N2 protection,The 1,4-dioxane (8 mL) was added to 5-chloro-pyrazolo [1,5-a] pyrimidine-3-carboxylate (0.08g, 0.37mmol),Xantphos (0.011 g, 0.02 mmol),Palladium acetate (4 mg, 0.02 mmol),Cesium carbonate (0.14 g, 0.42 mmol) andN- (3-aminobenzene) propionamide (0.08 g, 0.48 mmol)110 reflux reaction 6h,The filtrate was washed with water (30 mL)The aqueous phase was extracted with dichloromethane (30 mL x 3) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column separation (dichloromethane / methanol (v / v) = 30/1) gave brown solid,And then subjected to high performance chromatography to give 20 mg of a beige solid in a yield of 15.59%.

Reference： [1]Patent: CN106336413,2017,A .Location in patent: Paragraph 0814; 0815; 0816; 0817; 0818

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Historical Records

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[ 1224944-51-7 ]

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Ghs Precautionary Statements

Precautionary Statements-General
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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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P264	Wash hands thoroughly after handling.
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P270	Do not eat, drink or smoke when using this product.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
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Code	Phrase
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
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P334	Immerse in cool water/wrap n wet bandages.
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P411
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or 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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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
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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
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H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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. 1224944-51-7 ] {[proInfo.proName]}

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Druglikeness

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[ 1224944-51-7 ] Synthesis Path-Downstream 1~13

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Chlorides

Esters

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Other Aromatic Heterocycles

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[ 1224944-51-7 ]

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[ 1224944-51-7 ]