[ CAS No. 256935-76-9 ] {[proInfo.proName]}

Name: 256935-76-9|Imidazo[1,5-a]pyridine-6-carboxylic acid|98%
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SKU: A326902
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Quality Control of [ 256935-76-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 256935-76-9 ]

SDS Specification

Alternatived Products of [ 256935-76-9 ]

Product Details of [ 256935-76-9 ]

CAS No. :	256935-76-9	MDL No. :	MFCD11042992
Formula :	C₈H₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JUDANXSOGJLMJU-UHFFFAOYSA-N
M.W :	162.15	Pubchem ID :	22565897
Synonyms :

Calculated chemistry of [ 256935-76-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.15
TPSA :	54.6 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) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.13
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.03
Log Po/w (MLOGP) :	0.32
Log Po/w (SILICOS-IT) :	0.29
Consensus Log Po/w :	0.83

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.2
Solubility :	1.01 mg/ml ; 0.00626 mol/l
Class :	Soluble
Log S (Ali) :	-2.13
Solubility :	1.2 mg/ml ; 0.00742 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.45
Solubility :	5.77 mg/ml ; 0.0356 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.32

Safety of [ 256935-76-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 256935-76-9 ]

* 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 [ 256935-76-9 ]
Downstream synthetic route of [ 256935-76-9 ]

[ 256935-76-9 ] Synthesis Path-Upstream 1~2

1
[ 139183-89-4 ]
[ 256935-76-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 465 - 469

2
[ 139183-88-3 ]
[ 256935-76-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 465 - 469

[ 256935-76-9 ] Synthesis Path-Downstream 1~12

1
[ 13079-18-0 ]
[ 256935-76-9 ]
imidazo[1,5-<i>a</i>]pyridine-6-carboxylic acid [2-hydroxy-2-(3,4,5-trimethoxy-phenyl)-ethyl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 465 - 469

2
[ 139183-89-4 ]
[ 256935-76-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 465 - 469

3
[ 139183-88-3 ]
[ 256935-76-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 465 - 469

4
[ 256935-76-9 ]
6-[5-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazol-2-yl]-imidazo[1,5-<i>a</i>]pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 465 - 469

6
[ 256935-76-9 ]
[ 36805-97-7 ]
[ 910094-95-0 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; toluene; at 90℃; for 10h;	Synthesis of tert-butyl imidazo[1,5-a]pyridine-6-carboxylate 3.37 ml (14.06 mmol) of N,N-dimethylformamide di(tertbutyl)acetal are added to 570 mg (3.52 mmol) of <strong>[256935-76-9]imidazo[1,5-a]pyridine-6-carboxylic acid</strong> [described in Bioorg. Med. Chem. Lett., (2002), 12(3), 465-470] in a mixture of 5 ml of dimethylformamide and 5 ml of toluene and the mixture is heated at 90 C. for 6 hours. 3.37 ml (14.06 mmol) of N,N-dimethylformamide di(tert-butyl)acetal are again added to the reaction medium and the mixture is heated at 90 C. for a further 4 hours. The reaction medium is poured onto water and extracted with ethyl acetate. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The product is purified by filtration through a bed of silica, elution being carried out with a mixture of dichloromethane and methanol (98/2). After evaporation, 580 mg of a beige powder are obtained. Melting point: 77 C.; 1H NMR (d6-DMSO): 1.59 (9H, s), 7.71 (1H, d), 7.36 (1H, s), 7.58 (1H, d), 8.56 (1H, s), 9.03 (1H, s).

Reference： [1]Patent: US2008/108648,2008,A1 .Location in patent: Page/Page column 18

7
[ 256935-76-9 ]
C₁₆H₁₃N₃O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7965 - 7983

8
[ 256935-76-9 ]
N-(4-((2-aminophenyl)carbamoyl)benzyl)imidazo[1,5-a]pyridine-6-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7965 - 7983

9
[ 18469-52-8 ]
[ 256935-76-9 ]
C₁₇H₁₅N₃O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7965 - 7983

10
Ν,Ο-dimethylhydroxylamine hydrochloride [ No CAS ]
[ 256935-76-9 ]
N-methoxy-N-methylimidazo[1, 5-a]pyridine-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of imidazo[1,5-ajpyridine-6-carboxylic acid (70 mg, 432 iimol, 1.0eq) and HATU (197 mg, 518 iimol, 1.2 eq) in 1 mL ofDMF was added TEA (131 mg, 1.3 mmol, 3 eq). The mixture was stirred at 25C for 10 mm, and then N-methoxymethanamine hydrochloride (50.5 mg, 518 iimol, 1.2 eq) was added. The mixture was stirred at 25C for 12 hours. The reaction mixture was poured into 5 mL of ice-water and extracted with five 3 mL portions of ethyl acetate. The combined organic layers were dried with anhydrous Na2SO4,filtered and concentrated in vacuo. The residue was purified by prep-TLC (Si02) to afford 110 mg of cmde N-methoxy-N-methylimidazo[ 1,5-al pyridine-6-carboxamide as yellow oil.

Reference： [1]Patent: WO2018/119395,2018,A1 .Location in patent: Page/Page column 185

11
[ 256935-76-9 ]
imidazo[1,5-a]pyridine-6-carbaldehyde [ No CAS ]

Reference： [1]Patent: WO2018/119395,2018,A1

12
2-methyl-3-phenyl-4,5,6,7-tetrahydropyrazolo[3,4-c]pyridine [ No CAS ]
[ 256935-76-9 ]
imidazo[1,5-a]pyridin-6-yl(2-methyl-3-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethyl acetate; at 20℃; for 1h;Inert atmosphere;	General procedure: To a solution of 2-methyl-3-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine, Intermediate 1, (150 mg, 0.7 mmol) in dichloromethane (DCM) (5.0 mL) was added HATU (348 mg, 0.91 mmol), followed by DIPEA (0.6 mL, 3.5 mmol) and 1-naphthoic acid (222 mg, 1.3 mmol), and the mixture stirred at room temperature for 1 h. The reaction mixture was diluted with water and the aqueous layer extracted with DCM (*2). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase HPLC (Method A) to afford the title compound as a white solid (94 mg, 36% yield). MS (ESI): mass calcd. for C24H21N3O, 367.1; m/z found, 368.1 [M+H]+. 1H NMR (400 MHz, Methanol-d4) delta 8.12-7.93 (m, 2H), 7.89-7.74 (m, 1H), 7.67-7.35 (m, 9H), 5.20-4.92 (m, 2H), 4.46-4.22 (m, 1H), 4.13-3.98 (m, 0.3H), 3.76 (d, J=54.9 Hz, 3H), 3.52-3.41 (m, 1H), 2.93-2.75 (m, 0.7H), 2.57-2.30 (m, 1H).

Reference： [1]Patent: US2020/102303,2020,A1 .Location in patent: Paragraph 0371; 0713-0714; 0865-0866

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Code	Phrase
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P391	Collect spillage. Hazardous to the aquatic environment
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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:
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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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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H229	Pressurized container: may burst if heated
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
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Health hazards
Code	Phrase
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
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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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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. 256935-76-9 ] {[proInfo.proName]}

Quality Control of [ 256935-76-9 ]

Related Doc. of [ 256935-76-9 ]

Product Details of [ 256935-76-9 ]

Calculated chemistry of [ 256935-76-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 256935-76-9 ]

Application In Synthesis of [ 256935-76-9 ]

[ 256935-76-9 ] Synthesis Path-Upstream 1~2

[ 256935-76-9 ] Synthesis Path-Downstream 1~12

Related Functional Groups of [ 256935-76-9 ]

Carboxylic Acids

Related Parent Nucleus of [ 256935-76-9 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 256935-76-9 ]

Related Parent Nucleus of
[ 256935-76-9 ]