[ CAS No. 33252-28-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 33252-28-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 33252-28-7 ]

SDS Specification

Alternatived Products of [ 33252-28-7 ]

Product Details of [ 33252-28-7 ]

CAS No. :	33252-28-7	MDL No. :	MFCD00084941
Formula :	C₆H₃ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ORIQLMBUPMABDV-UHFFFAOYSA-N
M.W :	138.55	Pubchem ID :	5152094
Synonyms :		Chemical Name :	6-Chloronicotinonitrile

Safety of [ 33252-28-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 33252-28-7 ]

* 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 [ 33252-28-7 ]
Downstream synthetic route of [ 33252-28-7 ]

[ 33252-28-7 ] Synthesis Path-Upstream 1~2

1
[ 33252-28-7 ]
[ 75-86-5 ]
[ 20730-07-8 ]

Reference： [1] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1540 - 1545

2
[ 33252-28-7 ]
[ 67-63-0 ]
[ 195140-86-4 ]

Reference： [1] Patent: US2010/249071, 2010, A1, . Location in patent: Page/Page column 51
[2] Patent: WO2008/130320, 2008, A2, . Location in patent: Page/Page column 152-153

[ 33252-28-7 ] Synthesis Path-Downstream 1~10

1
[ 33252-28-7 ]
[ 25999-04-6 ]
N-(5-cyanopyridin-2-yl)morpholine-4-sulfamide [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 2705 - 2708

2
[ 33252-28-7 ]
[ 121148-00-3 ]
[ 401568-95-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2441 - 2445

3
[ 845305-83-1 ]
[ 33252-28-7 ]
[ 845306-22-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 60℃; for 4h;	Example 2 6- {4- [ (1-CYCLOBUTYL-4-PIPERIDINYL) OXY]-1-PIPERIDINYL}-3-PYRIDINECARBONITRILE hydrochloride (E2) Step 1: tert-Butyl 4- ( [L- (5-CYANO-2-PYRIDINYL)-4-PIPERIDINYL] OXY)-L- piperidinecarboxylate tert-Butyl 4- (4-piperidinyloxy)-1-piperidinecarboxylate (D4) (0.118g) was reacted with 2- chloro-5-cyano-pyridine (0.0573g) in DMSO (5ML) containing potassium carbonate (0.069g) for 4h at 60C. The reaction was then evaporated to a minimum volume and the residue redissolved in DCM (20MOL) and washed with saturated sodium hydrogen carbonate solution. Evaporation of the dried (MgSO4) organic layer provided the subtitle compound as an oil which crystallised on standing (0.191g).

Reference： [1]Patent: WO2005/14571,2005,A1 .Location in patent: Page/Page column 32-33

4
[ 33252-28-7 ]
[ 74879-18-8 ]
[ 1057682-03-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine; In N,N-dimethyl-formamide; at 20.0℃; for 14.0h;	Triethylamine (4.13 g, 3 niL, 40.8 mmol, 4 eq) is added to a solution of 6-chloro- nicotinonitrile (1.38 g, 10 mmol, leq), (S)-2-methyl- piperazine (1.0Og, 10 mmol, leq) in DMF (15 niL), and the resulting solution is stirred at rt for 14 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (1.4 g, 69%). 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 8.38 (s, 1 H), 7.58 (d, J=9.60 Hz, 1 H), 6.59 (d, J=9.09 Hz, 1 H), 4.19 - 4.31 (m, 2 H), 3.08 - 3.15 (m, 1 H), 2.92 - 3.04 (m, 1 H), 2.81 - 2.91 (m, 2 H), 2.57 - 2.65 (m, 1 H), 1.15 (d. J=6.32 Hz, 3 H).
67%	With potassium carbonate; In N,N-dimethyl acetamide; at 60.0℃; for 2.0h;	To a stirred solution of (2S)-2-methylpiperazine (0.30 g, 2.1 mmol) in DMA (6 mL), 6-chloropyridine-3-carbonitrile (0.29 g, 2.3 mmol) and K2C03 were added. The resultantreaction mixture was heated to 60 C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was diluted with cold water (20 mL) and extractedwith EtOAc (3 x 25 mL). The combined organic extracts were washed with cold water (20mL) and brine (2 x 20 mL). The organic layer was separated, dried over Na2S04 andconcentrated under reduced pressure to give the crude residue which was purified by columnchromatography (100-200 silica gel, 10 g, 10% MeOH-DCM) to furnish 6-[(3S)-3-methylpiperazin-1-yl]pyridine-3-carbonitrile (0.29 g, 67%) as an off-white solid.LCMS: m/z: 203.4 [M+Ht.

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3954 - 3968
[2]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 34
[3]Patent: WO2018/125961,2018,A1 .Location in patent: Page/Page column 110; 113

5
[ 33252-28-7 ]
[ 255735-88-7 ]
[ 1059191-62-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 90℃; for 12h;Inert atmosphere;	Example 38A; tert-Butyl {2-[(5-cyanopyridin-2-yl)amino]propyl}carbamate 2-Chloro-5-cyanopyridine (477 mg, 3.4 mmol), tert-butyl (2-aminopropyl)carbamate (300 mg, 1.7 mmol) and potassium bicarbonate (345 mg, 3.4 mmol) are dissolved in DMF (10 ml) and stirred at 90° C. under argon for 12 h. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3.x.75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. After removal of the solvent, the residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1). 265 mg (55percent of theory) of the product are obtained as a solid.LCMS (method 4): Rt=3.21 min. (m/z=277 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.37 (d, 1H), 7.66 (d, 1H), 7.37 (d, 1H), 6.87 (br t, 1H), 6.50 (d, 1H), 4.05 (m, 1H), 3.02 (m, 2H), 1.37 (s, 9H), 1.07 (d, 3H).

Reference： [1]Patent: US2010/113441,2010,A1 .Location in patent: Page/Page column 33

6
[ 33252-28-7 ]
[ 1000796-62-2 ]
[ 1062196-26-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 140.0℃; for 0.75h;Microwave irradiation;	Example 67A; tert-Butyl 3-[(5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate In analogy to the preparation of Example 60A, 85 mg (56% of theory) of the product are obtained as a solid from 100 mg (0.49 mmol) of <strong>[1000796-62-2]tert-butyl 3-aminopiperidine-1-carboxylate hydrochloride</strong> and 138 mg (0.99 mmol) of 6-chloropyridine-3-carbonitrile.LCMS (method 6): Rt=1.81 min. (m/z=303 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.40 (d, 1H), 7.68 (d, 1H), 7.53 (d, 1H), 6.59 (d, 1H), 4.12 (s, br, 3H), 3.80 (s, br, 1H), 3.1-3.7 (m, 2H), 1.90 (m, 1H), 1.74 (m, 1H), 1.3-1.6 (m, 1H), 1.27 (s, 9H).

Reference： [1]Patent: US2010/113441,2010,A1 .Location in patent: Page/Page column 40

7
[ 33252-28-7 ]
[ 1196473-37-6 ]
[ 1196473-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 85℃;	To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (0.47 g, 3.13 mmol) in anhydrous DMF (15 mL) were added K2CO3 (1.30 g, 9.4 mmol) and 6-chloro-nicotinonitrile (0.868 g, 6.27 mmol) at room temperature. After stirring for 18 h at 85° C., the reaction mixture was cooled to room temperature. The solid was filtered out and dissolved into water (20 mL) and acidified to pH 3 using diluted hydrochloric acid. The precipitate was collected and washed with water and dried to give 0.612 g of crude product which was purified by recrystallization from EtOAc/hexanes to give 0.361 g of pure product as a white solid. Mp 156-157° C. 1HNMR (400 MHz, DMSO-d6) delta 9.25 (s, 1H), 8.64 (d, J=2.05 Hz, 1H), 8.33 (dd, J=8.50, 2.34 Hz, 1H), 7.40-7.53 (m, 2H), 7.19-7.32 (m, 2H), 5.02 (s, 2H). MS (ESI) m/z=253 [M+H]+.

Reference： [1]Patent: US2010/256092,2010,A1 .Location in patent: Page/Page column 83

8
[ 33252-28-7 ]
[ 1072-84-0 ]
[ 1343075-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120℃;	Intermediate 631 -(5-Cvanopyridin-2-yl)-1 H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> A mixture of 1 H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> (500 mg), 6-chloropyridine-3-carbonitrile (0.93 g), and N,N-diisopropyl-ethyl-amine (3.6 mL) in N,N-dimethylformamide (6 mL) is heated to 120 °C overnight. The crude product is purified by HPLC. LC (method 20): tR = 1 .73 min; Mass spectrum (APCI): m/z = 215 [M+H]+.
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120℃;	1-(5-Cyanopyridin-2-yl)-1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> A mixture of 1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> (500 mg), 6-chloropyridine-3-carbonitrile (0.93 g), and N,N-diisopropyl-ethyl-amine (3.6 mL) in N,N-dimethylformamide (6 mL) is heated to 120° C. overnight. The crude product is purified by HPLC. LC (method 20): tR=1.73 min; Mass spectrum (APCI): m/z=215 [M+H]+.

Reference： [1]Patent: WO2012/168315,2012,A1 .Location in patent: Page/Page column 103-104
[2]Patent: US2013/143892,2013,A1 .Location in patent: Paragraph 0388; 0389

9
[ 33252-28-7 ]
[ 35344-95-7 ]
6-(4-formyl-1H-pyrazol-1-yl)nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1 g	With potassium acetate; In dimethyl sulfoxide; at 100℃; for 2h;	To a solution of <strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (500 mg, 5 mmol) and 6- chloronicotinonitrile (700 mg, 5 mmol ) in 20 mL DMSO was added KOAc (2.1 g, l5mmol). The resulting mixture was stirred at 100°C for 2 hours. The resulting mixture was concentrated and the crude product was purified by flash column chromatography to give the 6-(4-formyl- 1H- pyrazol-1-yl)nicotinonitrile (1.0 g). The structure was confirmed by LC-MS

Reference： [1]Patent: WO2016/127074,2016,A1 .Location in patent: Page/Page column 38

10
[ 858671-91-7 ]
[ 33252-28-7 ]
tert-butyl 5-(5-cyanopyridin-2-yl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h;	A solution of <strong>[858671-91-7]tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate</strong> (1 g, 4.71 mmol, 1.00 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), 6-chloropyridine-3-carbonitrile (651 mg, 4.70 mmol, 1.00 equiv) in DMF (10 mL) was stirred for 2 h at 80 C. in an oil bath. After concentration, the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (1:3) to afford 940 mg (63%) of the title compound as a solid. LCMS (ESI, m/z): 315.17 [M+H]+

Reference： [1]Patent: US2019/330194,2019,A1 .Location in patent: Paragraph 1171

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Blaise Reaction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction

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[ 33252-28-7 ]

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Ghs Precautionary Statements

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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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[ CAS No. 33252-28-7 ] {[proInfo.proName]}

Quality Control of [ 33252-28-7 ]

Related Doc. of [ 33252-28-7 ]

Product Details of [ 33252-28-7 ]

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Application In Synthesis of [ 33252-28-7 ]

[ 33252-28-7 ] Synthesis Path-Upstream 1~2

[ 33252-28-7 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 33252-28-7 ]

Chlorides

Nitriles

Related Parent Nucleus of [ 33252-28-7 ]

Pyridines

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[ 33252-28-7 ]

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[ 33252-28-7 ]