76292-67-6|Ethyl imidazo[1,5-a]pyridine-5-carboxylate| Ambeed

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Quality Control of [ 76292-67-6 ] Purity: 98% SDS Specification

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Product Details of [ 76292-67-6 ]

CAS No. :	76292-67-6
Formula :	C₁₀H₁₀N₂O₂
M.W :	190.20
SMILES Code :	CCOC(=O)C1=CC=CC2=CN=CN12
MDL No. :	MFCD23135762
InChI Key :	ZHDWLOWRAYJJMT-UHFFFAOYSA-N
Pubchem ID :	12624795

Safety of [ 76292-67-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 76292-67-6 ]

* 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 [ 76292-67-6 ]

[ 76292-67-6 ] Synthesis Path-Downstream 1~22

1
[ 76266-08-5 ]
[ 76292-67-6 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2195 - 2196.

2
[ 76259-00-2 ]
[ 76292-67-6 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2195 - 2196.

3
[ 76266-04-1 ]
[ 76292-67-6 ]

References: [1]Tetrahedron Letters,1980,vol. 21,p. 2195 - 2196.

4
[ 76292-67-6 ]
[ 873785-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; at 60.0℃; under 2999.54 Torr; for 2.0h;	30 ml of cone. HCI and 0.750 g of 10% Pd/C are added to a solution of 15.770 mmol of ethylimidazo[1,5-a]pyridine-5-carboxylate [76292-67-6] in 100 ml of ethanol. The reaction mixtureis subsequently hydrogenated at 58 psi and 60C for 2 hours. The catalyst is filtered off viaHyflo and the filtrate is concentrated. The crude title compound is obtained from the residueas an amber-coloured oil. Rf = 0.37 (toluene/methanol = 85:15); Rt = 4.19.

References: [1]Patent: WO2006/5725,2006,A2 .Location in patent: Page/Page column 18.

5
[ 104086-21-7 ]
[ 76292-67-6 ]

References: [1]Patent: WO2016/161960,2016,A1 .

6
ethyl 6-(formamidomethyl)picolinate [ No CAS ]
[ 76292-67-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In toluene; at 80.0℃; for 2.0h;	To a solution of ethyl 6-(formamidomethyl)picolinate (23 g, 110 mmol) in toluene (400 mL) was added POC13 (23 mL) at room temperature and the mixture was heated at 80C for 2 hours. Then cooled to room temperature and evaporated the solvent under reduced pressure before HC1 (400 mL, iN) was added to the residue, extracted with EA (200 mL2), isolated theaqueous layer, adjusted pH=7-8 with saturated aqueous of NaOH before extracted with EA (400 mL2), combined the organic layers, evaporated the solvent under reduced pressure to give crude solid (13g in 62% yield) as a brown solid. ‘H NMR (DMSO-d6) ö 9.13 (s, 1H), 7.98 (d, 1H,J=8.8 Hz), 7.67 (s, 1H), 7.64 (dd, 1H,J=6.8 Hz), 4.24 (q, 2H,J=6.4 Hz), 1.39 (t, 3H,J=7.2 Hz).

References: [1]Patent: WO2016/161960,2016,A1 .Location in patent: Paragraph 0140.

7
[ 76292-67-6 ]
imidazo [1,5-a]pyridin-5-ylmethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In ethanol; at 80.0℃; for 1.0h;	To a solution of ethyl imidazo[1,5-a]pyridine-5-carboxylate (36 g, 189 mmol) in EtOH (1L) was added batch wise of NaBH4 (14.3 g, 379 mmol) at 80C and the mixture was stirred at 80C for lh. Then evaporated the solvent under reduced pressure and water (100 mL) was added to the residue, extracted with EA (400 mL*2), combined the organic layer, dried over Na2504,filtered to remove the solid, the filtrate was evaporated under reduced pressure to give crudeproduct (27.9 g) and this crude product was used for next step without further purification. ‘HNMR (DMSO-d6) ö 8.33 (s, 1H), 7.53 (d, 1H, J=8.8 Hz), 7.79-6.83 (m, 1H), 6.68 (dd, 1H, J=6.4Hz), 5.73(s, 1H), 4.76 (s, 2H).

References: [1]Patent: WO2016/161960,2016,A1 .Location in patent: Paragraph 0141.

8
[ 76292-67-6 ]
[ 85691-71-0 ]

References: [1]Patent: WO2016/161960,2016,A1 .

9
[ 76292-67-6 ]
cyclohexyl(imidazo[1,5-a]pyridin-5-yl)methanol [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

10
[ 76292-67-6 ]
(S)-cyclohexyl({imidazo[1,5-a]pyridin-5-yl})methanol [ No CAS ]
(R)-cyclohexyl({imidazo[1,5-a]pyridin-5-yl})methanol [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

11
[ 76292-67-6 ]
cycloheptyl(imidazo[1,5-a]pyridin-5-yl)methanol [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

12
[ 76292-67-6 ]
tert-butyl 4-(imidazo[1,5-a]pyridine-5-carbonyl)piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

13
[ 76292-67-6 ]
tert-butyl 4-(hydroxy(imidazo[1,5-a]pyridin-5-yl)methyl)piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

14
[ 76292-67-6 ]
imidazo[1,5-a]pyridine-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20.0℃;	To a solution of ethyl imidazo[1,5-a]pyridine-5-carboxylate (2.0 g, 10.5 mmol,Compound of Step 6 in Example A001) in a mixture of THF (20 mL) and water (5 mL) was added lithium hydroxide hydrate (881 mg, 2 eq) at room temperature and the mixture was stirred overnight. Evaporated the solvent under reduced pressure and water (80 mL) was added to the residue and adjust pH=6-7 with HC1 (4 N) and the yellow precipitate was collected by filtration to give 1.lg in 65% yield. ‘H NMR (DMSO-d6) ö 9.20 (s, 1H), 7.90 (d, 1H, J=9.2 Hz), 7.61 (s, 1H), 7.57 (dd, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=9.2 Hz).

References: [1]Patent: WO2016/161960,2016,A1 .Location in patent: Paragraph 0161.

15
[ 76292-67-6 ]
N-methoxy-N-methylimidazo [1,5-a]pyridine-5-carboxamide [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

16
[ 76292-67-6 ]
cyclohexyl(imidazo[1,5-a]pyridin-5-yl)methanone [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

17
[ 76292-67-6 ]
5-(cyclohexylmethyl)imidazo[1,5-a]pyridine [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

18
[ 76292-67-6 ]
1-cyclohexyl-1-(imidazo[1,5-a]pyridin-5-yl)ethan-1-ol [ No CAS ]

References: [1]Patent: WO2016/161960,2016,A1 .

19
[ 15658-60-3 ]
[ 76292-67-6 ]

References: [1]Patent: WO2016/161960,2016,A1 .

20
[ 41337-81-9 ]
[ 76292-67-6 ]

References: [1]Patent: WO2016/161960,2016,A1 .

21
[ 49668-99-7 ]
[ 76292-67-6 ]

References: [1]Patent: WO2016/161960,2016,A1 .

22
[ 944150-30-5 ]
[ 76292-67-6 ]

References: [1]Patent: WO2016/161960,2016,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Preparation of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 76292-67-6 ]

Esters

A503329 [141912-71-2]

Methyl imidazo[1,5-a]pyridine-5-carboxylate

Similarity: 0.97

A248323 [119448-87-2]

Ethyl imidazo[1,5-a]pyridine-1-carboxylate

Similarity: 0.91

A468635 [1427448-43-8]

Methyl 7-chloroimidazo[1,5-a]pyridine-5-carboxylate

Similarity: 0.90

A752738 [177485-39-1]

Ethyl imidazo[1,2-a]pyridine-5-carboxylate

Similarity: 0.90

A395355 [1039356-98-3]

Methyl imidazo[1,5-a]pyridine-1-carboxylate

Similarity: 0.88

Related Parent Nucleus of
[ 76292-67-6 ]

Other Aromatic Heterocycles

A503329 [141912-71-2]

Methyl imidazo[1,5-a]pyridine-5-carboxylate

Similarity: 0.97

A248323 [119448-87-2]

Ethyl imidazo[1,5-a]pyridine-1-carboxylate

Similarity: 0.91

A468635 [1427448-43-8]

Methyl 7-chloroimidazo[1,5-a]pyridine-5-carboxylate

Similarity: 0.90

A752738 [177485-39-1]

Ethyl imidazo[1,2-a]pyridine-5-carboxylate

Similarity: 0.90

A395355 [1039356-98-3]

Methyl imidazo[1,5-a]pyridine-1-carboxylate

Similarity: 0.88

Precautionary Statements-General
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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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.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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Health hazards
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H302	Harmful if swallowed
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H316	Causes mild skin irritation
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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

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CAS No.: 76292-67-6

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