[ CAS No. 1150561-70-8 ]

Name: 1150561-70-8|3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile|95%
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SKU: A535488
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Quality Control of [ 1150561-70-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1150561-70-8 ]

SDS Specification

Alternatived Products of [ 1150561-70-8 ]

Product Details of [ 1150561-70-8 ]

CAS No. :	1150561-70-8	MDL No. :	MFCD12026105
Formula :	C₁₃H₁₇BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HQSMPPQBXULOMO-UHFFFAOYSA-N
M.W :	244.10 g/mol	Pubchem ID :	46739526
Synonyms :

Calculated chemistry of [ 1150561-70-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.39
TPSA :	55.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.26
Log Po/w (WLOGP) :	1.56
Log Po/w (MLOGP) :	0.19
Log Po/w (SILICOS-IT) :	1.8
Consensus Log Po/w :	1.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.96
Solubility :	0.269 mg/ml ; 0.0011 mol/l
Class :	Soluble
Log S (Ali) :	-3.05
Solubility :	0.215 mg/ml ; 0.000882 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.1
Solubility :	0.0192 mg/ml ; 0.0000787 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.09

Safety of [ 1150561-70-8 ]

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

Application In Synthesis of [ 1150561-70-8 ]

* 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 [ 1150561-70-8 ]
Downstream synthetic route of [ 1150561-70-8 ]

[ 1150561-70-8 ] Synthesis Path-Upstream 1~3

1
[ 73183-34-3 ]
[ 156072-86-5 ]
[ 1150561-70-8 ]

Reference： [1] Patent: EP2719697, 2014, A1, . Location in patent: Paragraph 0219; 0222; 0223

2
[ 123-91-1 ]
[ 156072-86-5 ]
[ 1150561-70-8 ]

Reference： [1] Patent: US2014/93505, 2014, A1, . Location in patent: Page/Page column

3
[ 3430-18-0 ]
[ 1150561-70-8 ]

Reference： [1] Patent: US2014/93505, 2014, A1,
[2] Patent: EP2719697, 2014, A1,

[ 1150561-70-8 ] Synthesis Path-Downstream 1~6

1
[ 1416000-57-1 ]
[ 1150561-70-8 ]
[ 1416000-33-3 ]

Yield	Reaction Conditions	Operation in experiment
31.6%	With tetrakis(triphenylphosphine) palladium(0); In dichloromethane;	3. Preparation of 3-methyl-5-(9-oxo-10-(3-(trifluoromethyl)phenyl)-9,10-dihydropyrido[3,2-c][1,5]naphthyridin-2-yl)-2-cyanopyridine To the cooled reaction liquor of <strong>[1150561-70-8]3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyanopyridine</strong> obtained in the above step, was added 2-chloro-10-(3-(trifluoromethyl)phenyl)pyrido[3,2-c][1,5]naphthyridin-9(10H)-one (500 mg, 1.33 mmol), palladium tetrakis(triphenylphosphine) (15 mg) and 2N sodium carbonate solution (3.0 mL). This system was reacted in a nitrogen-protecting atmosphere at 90 C. for 16 hrs. The reaction mixture was cooled to room temperature and filtered. The organic layer was separated out, concentrated in a reduced pressure, dissolved in dichlormethane, successively washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated, and purified with a silica-gel column chromatography (ethyl acetate) to produce 192 mg of the target compound in a yield of 31.6%. Formula: C25H14F3N5O MW: 457.12 MS (M+H): 458.1 1H-NMR (d6-DMSO, 400 MHz): delta 9.30 (1H, s), 8.58 (1H, d), 8.40 (1H, d), 8.38 (1H, d), 8.20 (1H, d), 7.87 (1H, d), 7.82-7.72 (4H, m), 7.02 (1H, d), 2.52 (3H, s).
31.6%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 90.0℃; for 16.0h;Inert atmosphere; Cooling;	3. Preparation of 3-methyl-5-(9-oxo-10-(3-(trifluoromethyl)phenyl)-9,10-dihydropyrido[3,2-c][1,5 ]naphthyridin-2-yl)-2-cyanopyridine To the cooled reaction liquor of <strong>[1150561-70-8]3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyanopyridine</strong> obtained in the above step, was added 2-chloro-10-(3-(trifluoromethyl)phenyl)pyrido[3,2-c][1,5]naphthyridin-9(10H)-o ne(500mg, 1.33mmol), palladium tetrakis(triphenylphosphine) (15mg) and 2N sodium carbonate solution (3.0mL). This system was reacted in a nitrogen-protecting atmosphere at 90 C for 16hrs. The reaction mixture was cooled to room temperature and filtered. The organic layer was separated out, concentrated in a reduced pressure, dissolved in dichlormethane, sucessively washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated, and purified with a silica-gel column chromatography (ethyl acetate) to produce 192 mg of the target compound in a yield of 31.6%. Formula: C25H14F3N5O MW: 457.12 MS(M+H): 458.1 1H-NMR(d6-DMSO, 400 MHz):delta 9.30 (1H, s), 8.58 (1H, d), 8.40 (1H, d), 8.38 (1H, d), 8.20 (1H, d), 7.87 (1H, d), 7.82-7.72 (4H, m), 7.02 (1H, d), 2.52 (3H, s).

Reference： [1]Patent: US2014/93505,2014,A1 .Location in patent: Page/Page column
[2]Patent: EP2719697,2014,A1 .Location in patent: Paragraph 0219; 0224; 0225

2
[ 123-91-1 ]
[ 156072-86-5 ]
[ 1150561-70-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;	2. Preparation of 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyanopyridine To 1,4-dioxane (20 mL) was successively added 5-bromo-3-methyl-2-cyanopyridine (390 mg, 1.98 mmol), bis(pinacolato)diboron (754 mg, 2.97 mmol), potassium acetate (493 mg, 5.03 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichlormethane complex (20 mg). The resulting mixture was reacted under stirring in a nitrogen-protecting atmosphere at 90 C. for 12 hrs. The reaction mixture was cooled and directly used in the next step without a further treatment.

Reference： [1]Patent: US2014/93505,2014,A1 .Location in patent: Page/Page column

3
[ 3430-18-0 ]
[ 1150561-70-8 ]

Reference： [1]Patent: US2014/93505,2014,A1
[2]Patent: EP2719697,2014,A1

4
[ 73183-34-3 ]
[ 156072-86-5 ]
[ 1150561-70-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90.0℃; for 12.0h;Inert atmosphere;	2. Preparation of 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyanopyridine To 1,4-dioxane (20mL) was successively added 5-bromo-3-methyl-2-cyanopyridine (390mg, 1.98mmol), bis(pinacolato)diboron (754mg, 2.97mmol), potassium acetate (493mg, 5.03mmol) and [1,1'-bis(diphenylphosphino)ferrocene] palladium(II) chloride dichlormethane complex(20mg). The resulting mixture was reacted under stirring in a nitrogen-protecting atmosphere at 90C for 12hrs. The reaction mixture was cooled and directly used in the next step without a further treatment.

Reference： [1]Patent: EP2719697,2014,A1 .Location in patent: Paragraph 0219; 0222; 0223

5
[ 1150561-70-8 ]
(4S)-7-chloro-N-(pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide [ No CAS ]
(9S)-5-(6-cyano-5-methylpyridin-3-yl)-N-(pyrazin-2-yl)-1,6,8-triazatricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.9%	With potassium phosphate; palladium diacetate; XPhos; In 1,4-dioxane; water; at 90.0℃; for 16.0h;Inert atmosphere;	To a degassed solution of (4S)-7-chloro-N-(pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (500 mg, 1.579 mmol), <strong>[1150561-70-8]3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile</strong> (501 mg, 2.052 mmol) and K3PO4 (1.005 g, 4.74 mmol) in 1,4-dioxane (20 mL) and water (3 mL), was added X-phos (75 mg, 0.158 mmol) and Pd(OAc)2 (17.72 mg, 0.079 mmol). The reaction mixture was further degassed for 15 min and the reaction mixture was stirred for 16 h at 90 C. The reaction mixture was cooled to 28 C. and filtered through a pad of celite and filtrate was evaporated to give residue. The residue was diluted with water (20 mL) and extracted with ethyl acetate (2×70 mL). The combined organic layer was washed with water (10 mL) followed by brine solution (10 mL). Organic layer was dried over anhydrous sodium sulfate, filtered and filtrate was evaporated to give crude. (TLC eluent: 100% Ethyl acetate, Rf-0.3; UV active). The crude compound was purified by column chromatography using neutral alumina, and the product was eluted with 55-60% ethyl acetate in hexane to afford pure (4S)-7-(6-cyano-5-methylpyridin-3-yl)-N-(pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (350 mg, 0.835 mmol, 52.9% yield) as pale yellow solid, LCMS (m/z): 399.22 [M+H]+. 1H NMR (400 MHz, CDCl3): delta 13.61 (s, 1H), 9.58 (d, J=1.5 Hz, 1H), 9.07 (d, J=2.2 Hz, 1H), 8.63-8.69 (m, 1H), 8.33 (d, J=2.8 Hz, 1H), 8.28 (dd, J=1.4, 2.6 Hz, 1H), 7.69 (d, J=8.1 Hz, 1H), 7.52 (m, J=8.1 Hz, 1H), 5.72 (dd, J=5.9, 3.07 Hz, 1H), 3.13-3.36 (m, 3H), 3.05 (dd, J=12.28, 3.3 Hz, 1H), 2.73 (S, 3H), 2.25-2.44 (m, 1H), 2.04-2.24 (m, 1H).

Reference： [1]Patent: US2015/152108,2015,A1 .Location in patent: Paragraph 1413; 1414; 1415

6
[ 1150561-70-8 ]
8-bromo-6-chloro-9-cyclopropylmethyl-1-methylpyrido[3,4-b]indole [ No CAS ]
[ 76-05-1 ]
5-(6-chloro-9-cyclopropylmethyl-1-methyl-9H-pyrido[3,4-b]indol-8-yl)-3-methylpyridine-2-carbonitrile trifluoroacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		Degassed dioxane (15 ml, abs.) and degassed water (4 ml) were charged in a 25 ml two-necked flask underargon. 8-Bromo-6-chloro-9-cyclopropylmethyl-1-methyl-pyrido[3,4-b]indole (300 mg, 0.86 mmol), sodium carbonate(272.8 mg, 2.57 mmol), 2-cyanopyridine-5-boronic acid pinacol ester (217.0 mg, 0.94 mmol) and BDFP (175.2 mg, 0.21mmol) were added, and the mixture was heated under reflux for 12 h. EA (5 ml) was added, the reaction mixture wasfiltered through a kieselgur cartridge and eluted with EA (4 x 10 ml). The combined organic phases were concentratedand the residue was purified by preparative HPLC. 149 mg (36%) of the title compound was obtained in the form of itssalt with trifluoroacetic acid.LC/MS (Method LC6): RT = 1.10 min; m/z = 373.2 [M+H]+

Reference： [1]Patent: EP3318563,2018,A1 .Location in patent: Paragraph 0252-0255

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Ghs Precautionary Statements

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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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
H227	Combustible liquid
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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
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

[ CAS No. 1150561-70-8 ]

Quality Control of [ 1150561-70-8 ]

Related Doc. of [ 1150561-70-8 ]

Product Details of [ 1150561-70-8 ]

Calculated chemistry of [ 1150561-70-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1150561-70-8 ]

Application In Synthesis of [ 1150561-70-8 ]

[ 1150561-70-8 ] Synthesis Path-Upstream 1~3

[ 1150561-70-8 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 1150561-70-8 ]

Organoboron

Nitriles

Related Parent Nucleus of [ 1150561-70-8 ]

Pyridines

Precautionary Statements-General

Prevention

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Storage

Disposal

Physical hazards

Health hazards

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Inquiry

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[ 1150561-70-8 ]

Related Parent Nucleus of
[ 1150561-70-8 ]