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[ CAS No. 1147558-43-7 ]

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DV 2D 3D

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Product Details of [ 1147558-43-7 ]

CAS No. :	1147558-43-7	MDL No. :	MFCD18426013
Formula :	C₇H₄ClFN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	170.57 g/mol	Pubchem ID :	68039995
Synonyms :

Safety of [ 1147558-43-7 ]

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

Application In Synthesis of [ 1147558-43-7 ]

Upstream synthesis route of [ 1147558-43-7 ]
Downstream synthetic route of [ 1147558-43-7 ]

[ 1147558-43-7 ] Synthesis Path-Upstream 1~1

1
[ 63069-50-1 ]
[ 1147558-43-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-chloro-succinimide In acetonitrile at 85℃; for 5 h;	4-Amino-3-chloro-5-fluorobenzonitrile A mixture of 4-amino-3-fluorobenzonitrile (1 equiv.) and N-chlorosuccinimide (1.5 equiv.) in acetonitrile (0.24 M) was stirred at 85° C. for 5 h. The solvent was removed by concentration and the residue was partitioned between ethyl acetate and 5percent NaOH. The organic phase was washed with 5percent NaOH and brine. Then the organic phase was dried over MgSO₄ and dried in vacuum to afford 4-amino-3-chloro-5-fluorobenzonitrile (88percent) as a beige solid. ¹H NMR (400 MHz, CDCl₃) δ ppm: 7.41 (t, J=6 Hz, 1H), 7.24 (dd, J=1.8, 10.2 Hz, 1H), 4.66 (s, 2H).

Reference： [1] Patent: US2016/96841, 2016, A1, . Location in patent: Paragraph 0281
[2] Patent: WO2012/174342, 2012, A1, . Location in patent: Page/Page column 45
[3] Patent: WO2013/12500, 2013, A1, . Location in patent: Page/Page column 61
[4] Patent: US2015/203455, 2015, A1, . Location in patent: Paragraph 0457-0458
[5] Patent: WO2015/110378, 2015, A1, . Location in patent: Paragraph 00260; 00312
[6] Patent: US9440929, 2016, B2, . Location in patent: Page/Page column 59
[7] Patent: WO2017/12647, 2017, A1, . Location in patent: Paragraph 0688

[ 1147558-43-7 ] Synthesis Path-Downstream 1~9

1
[ 63069-50-1 ]
[ 1147558-43-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-chloro-succinimide; In acetonitrile; at 85℃; for 5.0h;	4-Amino-3-chloro-5-fluorobenzonitrile A mixture of 4-amino-3-fluorobenzonitrile (1 equiv.) and N-chlorosuccinimide (1.5 equiv.) in acetonitrile (0.24 M) was stirred at 85 C. for 5 h. The solvent was removed by concentration and the residue was partitioned between ethyl acetate and 5% NaOH. The organic phase was washed with 5% NaOH and brine. Then the organic phase was dried over MgSO4 and dried in vacuum to afford 4-amino-3-chloro-5-fluorobenzonitrile (88%) as a beige solid. 1H NMR (400 MHz, CDCl3) delta ppm: 7.41 (t, J=6 Hz, 1H), 7.24 (dd, J=1.8, 10.2 Hz, 1H), 4.66 (s, 2H).
	With N-chloro-succinimide; In acetonitrile; at 86℃; for 6.0h;	INTERMEDIATE 74-Amino-3-chloro-5-fluorobenzonitrile A solution of 4-amino-3-fluorobenzonitrile (25.13 g, 185 mmol) and NCS (24.65 g, 185 mmol) in acetonitrile (500 mL) was stirred at 86 C (reflux) for 5 h. LCMS showed -17% of starting material remained. Additional NCS (0.2 eq) was added and the reaction was stirred for 1 h. The reaction was partly concentrated and the residue was partitioned between 5% NaOH (100 mL) and EtOAc. The aqueous layer was back extracted with EtOAc. The organic extracts were dried over Na2S04 and concentrated to a pink solid. The NMR spectrum showed some of the succinimate side product still remained. The crude product was washed with H20 and air dried to give the desired product as a beige solid. This product was used in the next step without any futher purification. MS (m/z) 171.1 (M+H+).
	With N-chloro-succinimide; In acetonitrile; at 86℃; for 6.0h;	4-Amino-3-chloro-5-fluorobenzonitrileA solution of 4-amino-3-fluorobenzonitrile (25.13 g, 185 mmol) and NCS (24.65 g, 185 mmol) in acetonitrile (500 mL) was stirred at 86 C (reflux) for 5 h. LCMS showed -17% of starting material remained. Additional NCS (0.2 eq) was added and the reaction was stirred for 1 h. The reaction was partly concentrated and the residue was partitioned between 5% NaOH (100 mL) and EtOAc. The aqueous layer was back extracted with EtOAc. The organic extracts were dried over Na2S04 and concentrated to a pink solid. The NMR spectrum showed some of the succinimate side product still remained. The crude product was washed with H20 and air dried to give the desired product as a beige solid. This product was used in the next step without any futher purification. MS (m/z) 171.1 (M+H+).

	With N-chloro-succinimide; acetic acid; at 70℃; for 16.0h;	1.13. Synthesis of 4-amino-3-chloro-5-fluoro-benzonitrile (Int.21) A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) was stirred at 70 C. for approximately 16 h. The mixture was concentrated. H2O was added to the residue and the solid product was filtered off and washed (sat. NaHCO3 and H2O). To eliminate H2O, THF was added and removed under reduced pressure to yield the desired product.
	With N-chloro-succinimide; acetic acid; at 70℃; for 16.0h;	1.13. Synthesis of 4-amino-3-chloro-5-fluoro-benzonitrile (mt. 21) j00260j A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) was stirred at 70C for approximately 16 h. The mixture was concentrated. H20 was added to the residue and the solid product was filtered off and washed (sat. NaHCO3 and H20). To eliminate H20, THF was added and removed under reduced pressure to yield the desired product.
	With N-chloro-succinimide; acetic acid; at 70℃; for 0.16h;	A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mE) was stirred at 70 C. for approximately 16 h. The mixture was concentrated. H20 was added to the residue and the solid product was filtered oil and washed (sat. NaHCO3 and H20). To eliminate H20, THF was added and removed under reduced pressure to yield the desired product.
	With N-chloro-succinimide; In acetic acid; at 70℃; for 16.0h;	3.123. Compound 111: (lR,2R)-N-[6-(2-chloro-4-cyano-6-fluoro-N-methyl-anilino)-l-methyl- 3.123.1. Step i): 4-amino-3-chloro-5-fluoro-benzonitrile A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) is stirred at 70C for approximately 16 h. The mixture is concentrated. H20 is added to the residue and the solid product is filtered off and washed (sat. NaHCC>3 and H20). To eliminate H20, THF is added and removed under reduced pressure to yield the desired product (Int. 21). 3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte

Reference： [1]Patent: US2016/96841,2016,A1 .Location in patent: Paragraph 0281
[2]Patent: WO2012/174342,2012,A1 .Location in patent: Page/Page column 45
[3]Patent: WO2013/12500,2013,A1 .Location in patent: Page/Page column 61
[4]Patent: US2015/203455,2015,A1 .Location in patent: Paragraph 0457-0458
[5]Patent: WO2015/110378,2015,A1 .Location in patent: Paragraph 00260; 00312
[6]Patent: US9440929,2016,B2 .Location in patent: Page/Page column 59
[7]Patent: WO2017/12647,2017,A1 .Location in patent: Paragraph 0688

2
[ 1147558-43-7 ]
[ 1273585-10-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium perborate tetrahydrate; acetic acid; In water; acetic acid; at 20 - 80℃; for 73.0h;	[0146] Sodium perborate tetrahydrate (131 g, 851 mmol) in acetic acid (200 mL) was heated to 60 C. A solution of<strong>[1147558-43-7]4-amino-3-chloro-5-fluorobenzonitrile</strong> (29.0 g, 170 mmol) in acetic acid (500 mL) was added dropwise, and the resultingreaction was stirred at 60C for 18 h. LCMS analysis indicated -50 % conversion. Additional sodium perborate tetrahydrate(14.4 g, 93.6 mmol) was added, and the reaction was stirred at 70C for 2 h followed by another addition of sodiumperborate tetrahydrate (70.0 g, 455 mmol). The reaction was stirred at 80 C for 5 h and then at rt for 2 d. The reactionwas poured into ice water, and the product was extracted into EtOAc. The combined organics were washed with waterand brine. Finally, the organics were dried over MgSO4, filtered, and concentrated to half volume. Addition of waterresulted in precipitation of the desired product which was collected in a frit, washed with water, and dried in vacuo toprovide an orange solid (27.5 g, 81 % crude yield). 1H NMR (400 MHz, CDCl3) delta 7.68 (s, 1H), 7.55 (d, 1 H).
	With sodium perborate; acetic acid; at 20 - 80℃; for 71.0h;	3-Chloro-5-fluoro-4-nitrobenzonitrile Sodium perborate tetrahydrate (131 g, 851 mmol) in acetic acid (200 mL) was heated to 60 C. A solution of <strong>[1147558-43-7]4-amino-3-chloro-5-fluorobenzonitrile</strong> (29.02 g, 170 mmol) in acetic acid (500 ml.) was added dropwise and the reaction was stirred at 60 C for 16 h. The LCMS the indicated the reaction showed -50% conversion. Additional sodium perborate tetrahydrate (14.4 g) was added and the reaction stirred at 70 C for 2 h. Then additional sodium perborate tetrahydrate (70 g) was added and the reaction was stirred at 80 C for 5 h, followed by RT for 2 days. The reaction was then poured into ice water and extracted with EtOAc (3x). The combined organic extracts were washed with H20 (2x), brine, dried over MgS04 and concentrated. When most of the acetic acid was evaporated, water was added to the residue. The orange precipitate was collected by filtration, washed with H20 and air dried to give the crude product as an orange solid. NMR showed the product contaminated with -10% of starting material. This product was used without any further purification.
	With sodium perborate tetrahydrate; acetic acid; at 20 - 80℃; for 71.0h;	3-Chloro-5-fluoro-4-nitrobenzonitrileSodium perborate tetrahydrate (131 g, 851 mmol) in acetic acid (200 mL) was heated to 60 C. A solution of <strong>[1147558-43-7]4-amino-3-chloro-5-fluorobenzonitrile</strong> (29.02 g, 170 mmol) in acetic acid (500 mL) was added dropwise and the reaction was stirred at 60 C for 16 h. The LCMS the indicated the reaction showed -50% conversion. Additional sodium perborate tetrahydrate (14.4 g) was added and the reaction stirred at 70 C for 2 h. Then additional sodium perborate tetrahydrate (70 g) was added and the reaction was stirred at 80 C for 5 h, followed by RT for 2 days. The reaction was then poured into ice water and extracted with EtOAc (3x). The combined organic extracts were washed with H20 (2x), brine, dried over MgS04 and concentrated. When most of the acetic acid was evaporated, water was added to the residue. The orange precipitate was collected by filtration, washed with H20 and air dried to give the crude product as an orange solid. NMR showed the product contaminated with -10% of starting material. This product was used without any further purification. 4-Chloro-1-r(3S,5S)-1-oxaspiror2.5loct-5-ylmethyll-1 H-benzimidazole-6-carbonitrile

Reference： [1]Patent: EP2720697,2016,B1 .Location in patent: Paragraph 0145; 0146
[2]Patent: WO2012/174342,2012,A1 .Location in patent: Page/Page column 45-46
[3]Patent: WO2013/12500,2013,A1 .Location in patent: Page/Page column 61

3
[ 463-71-8 ]
[ 1147558-43-7 ]
3-chloro-5-fluoro-4-isothiocyanatobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With N-ethyl-N,N-diisopropylamine; at 0 - 20℃;	3-Chloro-5-fluoro-4-isothiocyanatobenzonitrile To a mixture of <strong>[1147558-43-7]4-amino-3-chloro-5-fluorobenzonitrile</strong> (1 equiv.) and DIEA (3.5 equiv.) in DCM (1 M) was added thiophosgene (3.5 equiv.) at 0 C. The reaction was stirred at room temperature overnight. The solvent was removed and the residue was purified by preparative TLC to give 3-chloro-5-fluoro-4-isothiocyanatobenzonitrile (34%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm: 7.55 (t, J=1.6 Hz, 1H), 7.40 (dd, J=1.7, 8.5 Hz, 1H).

Reference： [1]Patent: US2016/96841,2016,A1 .Location in patent: Paragraph 0282

4
[ 1147558-43-7 ]
(1s,4s)-4-((5-(3-(2-chloro-4-cyano-6-fluorophenyl)thioureido)-2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)amino)cyclohexanecarboxamide [ No CAS ]

Reference： [1]Patent: US2016/96841,2016,A1

5
[ 1147558-43-7 ]
(1s,4s)-4-(8-(2-chloro-4-cyano-6-fluorophenylamino)-2-(tetrahydro-pyran-4-ylamino)-9H-purin-9-yl)cyclohexanecarboxamide [ No CAS ]

Reference： [1]Patent: US2016/96841,2016,A1

6
[ 1147558-43-7 ]
3-chloro-5-(((-7-methyl-3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)amino)-4-nitrobenzonitrile [ No CAS ]

Reference： [1]Patent: EP2720697,2016,B1

7
[ 1147558-43-7 ]
4-chloro-1-((-7-methyl-3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile trifluoroacetic acid salt [ No CAS ]

Reference： [1]Patent: EP2720697,2016,B1

8
[ 1147558-43-7 ]
6-chloro-N₂,N₂-bis(4-methoxybenzyl)-N₄-methyl-3-nitropyridine-2,4-diamine [ No CAS ]
4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2-pyridyl]amino]-3-chloro-5-fluorobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl acetamide; at 120℃; for 16.0h;	3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte A mixture of 6-chloro-N2,N2-bis[(4-methoxyphenyl)methyl]-N4-methyl-3-nitro-pyridine-2,4- diamine (3.39 mmol), <strong>[1147558-43-7]4-amino-3-chloro-5-fluoro-benzonitrile</strong> (6.78 mmol) and CS2CO3 (13.6 mmol) in DMA (15 mL) is stirred for 16 h at 120 C. A solution of saturated NH4C1 is added to the mixture. The solid is filtered out and further washed with water. The solid is taken up in EtOAc and the organic mixture is washed (H20 and brine), dried (Na2S04) and concentrated. The residue is purified by flash column chromatography (S1O2, 100:0 to 50:50 petroleum ether/EtOAc) to afford the desired product.

Reference： [1]Patent: WO2017/12647,2017,A1 .Location in patent: Paragraph 0689

9
[ 1147558-43-7 ]
6-chloro-N₂,N₂-bis(4-methoxybenzyl)-N₄-methyl-3-nitropyridine-2,4-diamine [ No CAS ]
4-[[4-[bis[(4-methoxyphenyl)methyl]amino]-1-methylimidazo[4,5-c]pyridin-6-yl]amino]-3-chloro-5-fluorobenzonitrile [ No CAS ]

Reference： [1]Patent: WO2017/12647,2017,A1

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Ghs Precautionary Statements

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P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

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
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
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