[ CAS No. 374537-97-0 ] {[proInfo.proName]}

Name: 374537-97-0|2-Amino-5-bromo-3,4-dimethylpyridine|97%
Brand: Ambeed
SKU: A504055
Price: 5.0 USD
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3d Animation Molecule Structure of 374537-97-0

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Quality Control of [ 374537-97-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 374537-97-0 ]

SDS Specification

Alternatived Products of [ 374537-97-0 ]

Product Details of [ 374537-97-0 ]

CAS No. :	374537-97-0	MDL No. :	MFCD02093947
Formula :	C₇H₉BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YAVKJNIMFGZBSY-UHFFFAOYSA-N
M.W :	201.06	Pubchem ID :	7010307
Synonyms :

Calculated chemistry of [ 374537-97-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.27
TPSA :	38.91 Å²

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) :	-6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.89
Log Po/w (XLOGP3) :	1.92
Log Po/w (WLOGP) :	2.05
Log Po/w (MLOGP) :	1.65
Log Po/w (SILICOS-IT) :	2.2
Consensus Log Po/w :	1.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.74
Solubility :	0.366 mg/ml ; 0.00182 mol/l
Class :	Soluble
Log S (Ali) :	-2.36
Solubility :	0.876 mg/ml ; 0.00436 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.3
Solubility :	0.101 mg/ml ; 0.000504 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 374537-97-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 374537-97-0 ]

* 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 [ 374537-97-0 ]

[ 374537-97-0 ] Synthesis Path-Downstream 1~14

1
[ 374537-97-0 ]
[ 20099-89-2 ]
[ 1016558-27-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 683 - 691

2
[ 374537-97-0 ]
[ 1097180-24-9 ]
[ 1097264-61-3 ]
C₂₀H₂₈BrN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 80℃; for 2h;	To a solution of 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.13 g, 0.39 mmol) in DMF (1 ml), <strong>[374537-97-0]5-bromo-3,4-dimethyl-2-pyridinamine</strong> (0.12 g, 0.59 mmol) was added and the mixture heated at 80 C. for 2 h. The reaction was eluted through a SCX column. Collected fractions gave 0.13 g of an oil containing a mixture of the final compound, the corresponding N-Boc protected derivative and some residual <strong>[374537-97-0]5-bromo-3,4-dimethyl-2-pyridinamine</strong>. [N-Boc derivative data: MS: (ES/+) m/z: 422 (M+1, 100%) and 424 (M+1, 100%). C20H28BrN3O2 requires 421]. The crude was dissolved in DCM (2.50 ml) and the resulting solution cooled to 0 C. TFA (0.50 ml) was added dropwise, the reaction left under stirring for 1 h and then eluted through a SCX column. Collected fractions gave the title compound D16 (0.090 g, 0.28 mmol, 72% yield from D2, two steps). MS: (ES/+) m/z: 322 (M+1, 100%) and 324 (M+1, 100%). C15H20BrN3 requires 321.

Reference： [1]Patent: US2009/22670,2009,A1 .Location in patent: Page/Page column 14

3
[ 374537-97-0 ]
5-bromo-3,4-dimethyl-1,2-dihydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sulfuric acid; sodium nitrite; In water; at 0 - 31℃; for 0.5h;	To a mixture of <strong>[374537-97-0]5-bromo-3,4-dimethylpyridin-2-amine</strong> (0.6 g, 3.0 mmol) and H2SO4 (98%, 1.62 mL) and H2O (18 mL) is added a solution of NaNO2 (243.6 mg, 4.2 mmol) in H2O (1.6 mL) drop-wise at 0 C. Then, it was stirred at 31 C. for 30 minutes and filtered. The resulting solid is washed with water to provide the title compound (375.0 mg, 62%) as a white solid. 1H NMR (CDCl3, 400 MHz) delta 7.48 (s, 1H), 2.32 (s, 3H), 2.19 (s, 3H). LCMS (M+H)+ 202.

Reference： [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0568; 0569

4
[ 374537-97-0 ]
5-bromo-1,3,4-trimethyl-1,2-dihydropyridin-2-one [ No CAS ]

Reference： [1]Patent: US2015/111885,2015,A1

5
[ 374537-97-0 ]
[ 98977-36-7 ]
tert-butyl 8-bromo-6,7-dimethyl-3,4-dihydroimidazo[1,2-a:5,4-b’]dipyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.16%		A mixture of <strong>[374537-97-0]5-bromo-3,4-dimethylpyridin-2-amine</strong> (1.0 g, 4.97 mmol), tert-butyl 3-oxopiperidine-1-carboxylate (0.991 g, 4.97 mmol), and acetic acid (0.028 mL, 0.497 mmol) in toluene (100 mL) was heated to reflux. Water was azeotroped using a Dean15 Stark apparatus. The mixture was heated at reflux for 2 days. After cooling to roomtemperature, air was bubbled through the reaction mixture for 2 h to promote oxidative dehydrogenation. The resulting solution was concentrated under high vacuum to afford a viscous oil. The oil was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The aqueous portion was back extracted with ethyl acetate.The combined organic portions were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified twice using silica gel column chromatography (100% EtOAc) to afford butyl 8-bromo-6,7-dimethyl-3,4- dihydroimidazo [1,2-a: 5,4-b?j dipyridine- 1 (2H)-carboxylate (242 mg, 0.605 mmol, 12.16% yield). LC/MS (M+H) 380.1, 382.1. ?HNMR(500MHz, chloroform-d) oe 8.06 (s, 1H),A mixture of <strong>[374537-97-0]5-bromo-3,4-dimethylpyridin-2-amine</strong> (1.0 g, 4.97 mmol), tert-butyl 3-oxopiperidine-1-carboxylate (0.991 g, 4.97 mmol), and acetic acid (0.028 mL, 0.497 mmol) in toluene (100 mL) was heated to reflux. Water was azeotroped using a Dean15 Stark apparatus. The mixture was heated at reflux for 2 days. After cooling to roomtemperature, air was bubbled through the reaction mixture for 2 h to promote oxidative dehydrogenation. The resulting solution was concentrated under high vacuum to afford a viscous oil. The oil was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The aqueous portion was back extracted with ethyl acetate.The combined organic portions were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified twice using silica gel column chromatography (100% EtOAc) to afford butyl 8-bromo-6,7-dimethyl-3,4- dihydroimidazo [1,2-a: 5,4-b?j dipyridine- 1 (2H)-carboxylate (242 mg, 0.605 mmol, 12.16% yield). LC/MS (M+H) 380.1, 382.1. ?HNMR(500MHz, chloroform-d) oe 8.06 (s, 1H)

Reference： [1]Patent: WO2016/149439,2016,A1 .Location in patent: Page/Page column 77

6
[ 374537-97-0 ]
[ 4637-24-5 ]
6-bromo-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		<strong>[374537-97-0]5-bromo-3,4-dimethylpyridin-2-amine</strong> (5.00 g, 24.87 mmol), DMF (10 mL) and Nu,Nu-dimethylformamide dimethyl acetal (11.15 mL, 83 mmol). The vial was heated to 80 C for 6 hours. The vial was cooled to room temperature. The volatiles were removed under vacuum and the resulting oil was dissolved in MeOH (5 mL) and pyridine (3.02 mL, 37.3 mmol) and cooled to 0 C. Hydroxylamine-O-sulfonic acid (4.22 g, 37.3 mmol) was added over 15 minutes and the mixture allowed to warm to room temperature overnight. The solution was concentrated under vacuum. The resulting white solid was partitioned between EtOAc and 1.5 M potassium phosphate solution. The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x50 mL). The combined organics were washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give a white solid. The solid was dissolved in DCM and MeOH and charged to an 80G silica gel column which was eluted with 0-100% ethyl acetate/hexane. Following concentration of the fractions, 6-bromo-7,8-dimethyl-[l,2,4]triazolo[l,5-a]pyridine (5.2 g, 23.00 mmol, 92 % yield) was collected as a whitish solid. LC-MS: M+l= 226/228, rt = 0.75 min, [Al]; NMR: NMR (400 MHz, CHLOROFORM-d) delta 8.68 (s, 1H), 8.26 (s, 1H), 2.68 (s, 3H), 2.50 (s, 3H).

Reference： [1]Patent: WO2018/5586,2018,A1 .Location in patent: Page/Page column 140; 141

7
[ 374537-97-0 ]
6-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/5586,2018,A1

8
[ 374537-97-0 ]
2-(4-(2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)acetamide [ No CAS ]

Reference： [1]Patent: WO2018/5586,2018,A1

9
[ 374537-97-0 ]
6-(3-isopropyl-5-(1-(2-(methylsulfonyl)ethyl)piperidin-4-yl)-1H-indol-2-yl)-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine [ No CAS ]

Reference： [1]Patent: WO2018/5586,2018,A1

10
[ 374537-97-0 ]
tert-butyl 4-(2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-isopropyl-1H-indol-5-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/5586,2018,A1

11
[ 374537-97-0 ]
5-bromo-3 4-dimethylpyridin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.3%	With sulfuric acid; sodium nitrite; In water; at 0 - 20℃; for 1h;	To a mixture of <strong>[374537-97-0]5-bromo-3,4-dimethylpyridin-2-amine</strong> (0.6 g, 2.98 mmol) in concentrated H2SO4 (2 mL) and water (15 mL) was added a solution of sodium nitrite (0.309 g, 4.48 mmol) in water (1.5 mL) at 0 C. The mixture was allowed to equilibrate to room temperature and stirred for 1 h. The precipitate was filtered and washed with water and dried to afford 5-bromo-3,4-dimethylpyridin-2-ol (400 mg, 1.980 mmol, 66.3 % yield), m/z (203, M+H).

Reference： [1]Patent: WO2019/28302,2019,A1 .Location in patent: Page/Page column 59

12
[ 374537-97-0 ]
5-bromo-2-chloro-3,4- dimethylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.7%	With hydrogenchloride; sodium nitrite; at -15 - 25℃; for 16h;	Procedure B: <strong>[374537-97-0]5-bromo-3,4-dimethylpyridin-2-amine</strong> (1.00 g, 4.97 mmol) was suspended in concentrated hydrochloric acid (23 mL) and was cooled to -15 C. Sodium nitrite (1.72 g, 24.9 mmol) was added slowly and the reaction mixture was slowly warmed to 25 C. After 16 hours, the reaction was quenched by addition of water and dichloromethane. The layers were separated, and the aqueous layer was extracted with dichloromethane (3 x 25 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford a crude orange solid. This crude material was purified by silica gel chromatography eluting with hexanes/EtOAc 100/0 to 0/100. Following concentration of the fractions, the product was isolated as a clear oil 5-bromo-2-chloro-3,4- dimethylpyridine (709 mg, 3.22 mmol, 64.7 % yield). LC retention time 0.97 min [TS 1].

Reference： [1]Patent: WO2019/28301,2019,A1 .Location in patent: Page/Page column 42

13
[ 374537-97-0 ]
2-amino-5-bromo-3-methylisonicotinaldehyde [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 4040 - 4049

14
[ 374537-97-0 ]
[ 420-37-1 ]
2-amino-5-bromo-1-methoxy-3,4-dimethylpyridin-1-ium tetrafluoroborate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 4040 - 4049

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Ghs Precautionary Statements

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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
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H228	Flammable solid
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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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

[ CAS No. 374537-97-0 ] {[proInfo.proName]}

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[ 374537-97-0 ] Synthesis Path-Downstream 1~14

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Bromides

Amines

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Pyridines

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