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[ CAS No. 74784-70-6 ] {[proInfo.proName]}

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Chemical Structure| 74784-70-6

Chemical Structure| 74784-70-6

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Quality Control of [ 74784-70-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 74784-70-6 ]

CAS No. :	74784-70-6	MDL No. :	MFCD00042164
Formula :	C₆H₅F₃N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RSGVKIIEIXOMPY-UHFFFAOYSA-N
M.W :	162.11	Pubchem ID :	735862
Synonyms :

Calculated chemistry of [ 74784-70-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.64
TPSA :	38.91 ?2

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) :	-6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	1.54
Log Po/w (WLOGP) :	2.84
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	1.66
Consensus Log Po/w :	1.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.15
Solubility :	1.14 mg/ml ; 0.00703 mol/l
Class :	Soluble
Log S (Ali) :	-1.97
Solubility :	1.75 mg/ml ; 0.0108 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.54
Solubility :	0.465 mg/ml ; 0.00287 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 74784-70-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 74784-70-6 ]

* 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.

Upstream synthesis route of [ 74784-70-6 ]
Downstream synthetic route of [ 74784-70-6 ]

[ 74784-70-6 ] Synthesis Path-Upstream 1~2

1
[ 74784-70-6 ]
[ 79456-30-7 ]

Yield	Reaction Conditions	Operation in experiment
96 g	With N-Bromosuccinimide In chloroform at 20 - 80℃; for 1.5 h; Cooling with ice	Production Example 59-1 71 g of N-bromosuccinimide was added to a mixture of 65 g of 5-trifluoromethyl-pyridine-2-ylamine and 100 mL of chloroform by being divided into 5 portions under ice water-cooling, The temperature was elevated to room temperature and the mixture was stirred for 1 hour. Then, the mixture was heated to 80°C and was heated and stirred for 3C minutes. After allowing the mixture to cool to room temperature, a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the mixture, which was then subjected to extraction using chloroform. A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 96 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine. 3-bromo-5-trifluoromethyl-pyridin-2-ylamine 1H-NMR (CDCl3) δ: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 12, p. 1715 - 1720
[2] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2777 - 2782
[3] Patent: US5861419, 1999, A,
[4] Patent: US6046217, 2000, A,
[5] Patent: US6004950, 1999, A,
[6] Patent: EP1012142, 2004, B1, . Location in patent: Page 27
[7] Patent: EP1015431, 2005, B1, . Location in patent: Page/Page column 23
[8] Patent: EP2865266, 2015, A1, . Location in patent: Paragraph 0676

2
[ 79456-29-4 ]
[ 74784-70-6 ]
[ 79456-30-7 ]

Reference： [1] Patent: US4349681, 1982, A,

[ 74784-70-6 ] Synthesis Path-Downstream 1~5

1
[ 74784-70-6 ]
[ 79456-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine; In hexane; acetic acid;	Step 1: 2-Amino-3-bromo-5-trifluoromethylpyridine To a solution of 2-amino-5-trifluoromethylpyridine (9 g) in acetic acid (75 mL) at r.t. was added bromine (5.8 mL) slowly. After 1 h, the acid was neutralized by the careful addition of sodium hydroxide (10N) at 0 C. The resulting orange precipitate was dissolved in ether and washed successively with saturated potassium carbonate, saturated Na2 SO3 and brine, dried and concentrated. The residual solid was stirred vigorously in hexane for 1 h to provide, after filtration, the title compound as a white solid (10.2 g).
	With sodium hydroxide; bromine; In hexane; acetic acid;	Step 1 2-Amino-3-bromo-5-trifluoromethylpyridine To a solution of 2-amino-5-trifluoromethylpyridine (9 g) in acetic acid (75 mL) at r.t. was added bromine (5.8 mL) slowly. After 1 h, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0 C. The resulting orange precipitate was dissolved in ether and washed successively with saturated potassium carbonate, saturated Na2 SO3 and brine, dried and concentrated. The residual solid was stirred vigorously in hexane for 1 h to provide, after filtration, the title compound as a white solid (10.2 g).
	With bromine; In acetic acid; at 20℃; for 1h;	To a solution of 2-amino-5-trifluoromethylpyridine (9 g) in acetic acid (75 mL) at r.t. was added bromine (5.8 mL) slowly. After 1 h, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0C. The resulting orange precipitate was dissolved in ether and washed successively with saturated potassium carbonate, saturated Na2SO3 and brine, dried and concentrated. The residual solid was stirred vigorously in hexane for 1 h to provide, after filtration, the title compound as a white solid (10.2 g).

	With bromine; acetic acid; at 18 - 25℃; for 1h;	EXAMPLE 13-(4-Methylsulfonyl)phenyl-2-pyrrolidin-1-yl-5-trifluoromethylpyridineStep 1: 2-Amino-3-bromo-5-trifluoromethylpyridine To a solution of 2-amino-5-trifluoromethylpyridine (9 g) in acetic acid (75 mL) at r.t. was added bromine (5.8 mL) slowly. After 1 h, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0C. The resulting orange precipitate was dissolved in ether and washed successively with saturated potassium carbonate, saturated Na2SO3 and brine, dried and concentrated. The residual solid was stirred vigorously in hexane for 1 h to provide, after filtration, the title compound as a white solid (10.2 g).
96 g	With N-Bromosuccinimide; In chloroform; at 20 - 80℃; for 1.5h;Cooling with ice;	Production Example 59-1 71 g of N-bromosuccinimide was added to a mixture of 65 g of 5-trifluoromethyl-pyridine-2-ylamine and 100 mL of chloroform by being divided into 5 portions under ice water-cooling, The temperature was elevated to room temperature and the mixture was stirred for 1 hour. Then, the mixture was heated to 80C and was heated and stirred for 3C minutes. After allowing the mixture to cool to room temperature, a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the mixture, which was then subjected to extraction using chloroform. A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 96 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine. 3-bromo-5-trifluoromethyl-pyridin-2-ylamine 1H-NMR (CDCl3) delta: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1715 - 1720
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2777 - 2782
[3]Patent: US5861419,1999,A
[4]Patent: US6046217,2000,A
[5]Patent: EP1012142,2004,B1 .Location in patent: Page 27
[6]Patent: EP1015431,2005,B1 .Location in patent: Page/Page column 23
[7]Patent: EP2865266,2015,A1 .Location in patent: Paragraph 0676

2
[ 74784-70-6 ]
[ 107867-51-6 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3719 - 3742
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 3679 - 3686
[3]Patent: US2014/315888,2014,A1
[4]Patent: EP2865266,2015,A1
[5]Patent: US5620978,1997,A

3
[ 70-23-5 ]
[ 74784-70-6 ]
[ 860457-99-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	In methanol; 1,2-dimethoxyethane; at 80℃; for 14.0h;	To a mixed solution of 5-(trifluoromethyl)pyridin-2-amine (835 mg, 5.15 mmol) in 1,2-dimethoxyethane (12.9 mL) and methanol (12.9 mL) was added ethyl bromopyruvate (776 μL, 6.18 mmol), and the mixture was stirred for 14 hours at 80C. After concentrating the reaction solution under reduced pressure, the residue was purified by silica gel column chromatography to give ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate (amount 557 mg, yield 42%).
42%	In methanol; 1,2-dimethoxyethane; at 80℃; for 14.0h;	5- (Trifluoromethyl) Pyridine-2-amine (835 mg, 5.15 mmol)In a mixed solution of 1,2-dimethoxyethane (12.9 mL) and methanol (12.9 mL)Ethyl bromopyruvic acid (776 μL, 6.18 mmol) was added, and the mixture was stirred at 80 C. for 14 hours.Residue after concentrating the reaction under reduced pressureWas purified by silica gel column chromatography to obtain ethyl 6- (trifluoromethyl) imidazole [1,2-a]pyridine-2-carboxylate (yield 557 mg, yield 42%).
	In ethanol; at 20 - 80℃; for 66.0h;	(a) 6-Trifluoromethyl-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester. A mixture of 3-bromo-2-oxo-propionic acid ethyl ester (6.4 mL, 50.9 mmol, Aldrich) and 5-trifluoromethyl-pyridin-2-ylamine (1.65 g, 10.2 mmol, Maybridge) in EtOH (20 mL) was heated at 80 C. for 48 h, and left at room temperature for 18 h. The white solid that precipitated was filtered, and the filter cake was rinsed with ether (10 mL), and dried in vacuo to provide the title compound. MS (ESI, pos. ion.) m/z: 258 (M+1).

	With Sodium hydrogenocarbonate; In ethanol; at 85℃; for 4.0h;	To a solution of 5-(trifluoromethyl)pyridin-2-amine (4.0 g, 25 mmol) in ethanol (40 mL) were added ethyl 3-bromo-2-oxo-propanoate (3.7 mL, 30 mmol) and sodium bicarbonate (4.1 g, 49 mmol) at room temperature. The reaction mass was heated at 85 C for 4 hours. After completion, the reaction mass 5 was added to ice cold water, solid was precipitated and the obtained solid was filtered through a Buchner funnel to afford ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate. This material was used as such in the next step. LCMS (Method 2): Rt = 1.35 min, m/z= 259 (M+H)+.
	With Sodium hydrogenocarbonate; In ethanol; at 85℃; for 4.0h;	To a solution of 5-(trifluoromethyl)pyridin-2-amine (4.0 g, 25 mmol) in ethanol (40 mL) were added ethyl 3-bromo-2-oxo-propanoate (3.7 mL, 30 mmol) and sodium bicarbonate (4.1 g, 49 mmol) at room temperature. The reaction mass was heated at 85 C for 4 hours. After completion, the reaction mass 5 was added to ice cold water, solid was precipitated and the obtained solid was filtered through a Buchner funnel to afford ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate. This material was used as such in the next step. LCMS (Method 2): Rt = 1.35 min, m/z= 259 (M+H)+.

Reference： [1]Patent: EP3851436,2021,A1 .Location in patent: Paragraph 0273-0274
[2]Patent: JP2021/138690,2021,A .Location in patent: Paragraph 0331-0333
[3]Patent: US2005/165049,2005,A1 .Location in patent: Page/Page column 23
[4]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1572 - 1575
[6]Patent: WO2022/49144,2022,A1 .Location in patent: Page/Page column 87-89
[7]Patent: WO2022/49144,2022,A1 .Location in patent: Page/Page column 87-89

4
[ 79456-29-4 ]
[ 74784-70-6 ]
[ 79456-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; sodium thiosulfate; acetic acid; In water;	EXAMPLE 4 Preparation of 2-Amino-3-bromo-5-trifluoromethylpyridine In a 100 ml four necked flask equipped with the same equipments as those used in Example 3 were placed 3 g of 2-amino-5-trifluoromethylpyridine and 30 ml of acetic acid to provide a homogeneous solution. 4.4 g of bromine was dropwise added thereto while cooling the flask with ice water at 10 to 20 C., and after completion of the dropwise addition, the mixture was reacted for 1 hour. The reaction product was poured into 200 ml of water, washed with an aqueous solution of sodium thiosulfate and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was evaporated off. The solid thus obtained was washed with n-hexane to obtain 3.5 g of the desired product.

Reference： [1]Patent: US4349681,1982,A

5
[ 74784-70-6 ]
[ 1036027-54-9 ]

Reference： [1]Patent: WO2017/31325,2017,A1
[2]Patent: WO2017/133667,2017,A1

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Amines ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

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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
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
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

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