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[ CAS No. 56874-97-6 ]

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3d Animation Molecule Structure of 56874-97-6

Chemical Structure| 56874-97-6

Chemical Structure| 56874-97-6

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Quality Control of [ 56874-97-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 56874-97-6 ]

CAS No. :	56874-97-6	MDL No. :	MFCD12913381
Formula :	C₇H₆FNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	155.13 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 56874-97-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.52
TPSA :	63.32 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) :	-6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	1.55
Log Po/w (WLOGP) :	1.05
Log Po/w (MLOGP) :	1.02
Log Po/w (SILICOS-IT) :	0.92
Consensus Log Po/w :	1.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.12
Solubility :	1.19 mg/ml ; 0.00766 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.503 mg/ml ; 0.00324 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.68
Solubility :	3.27 mg/ml ; 0.0211 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.01

Safety of [ 56874-97-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 56874-97-6 ]

* 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.

Downstream synthetic route of [ 56874-97-6 ]

[ 56874-97-6 ] Synthesis Path-Downstream 1~21

1
[ 91832-73-4 ]
[ 56874-97-6 ]
[ 117449-72-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2178 - 2199

2
[ 2417-72-3 ]
[ 56874-97-6 ]
[ 960250-49-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 2.0h;	To a solution of 5-fluoro-2-hydroxy-benzamide (13)(1.16g, 7.5mmol) in DMF (3OmL) was added potassium carbonate (2.2g, 16.0mmol) followed by methyl (4-bomomethyl) benzoate (1.82g, δ.Ommol), The mixture was heated for 2 hours at 900C. The reaction was then cooled to ambient temperature, a fine white suspension resulted. The reaction was concentrated in vacuo and the resultant cream precipitate was washed with water (2x 30ml) and then plug washed with diethyl ether (2x 25ml) and dried to afford a white solid. Single peak in LC-MS analysis, (2.2Og, 93% yield) requiring no further purification; m/z (LC-MS, ESP), RT=3.56min, (M+H)=304.0.

Reference： [1]Patent: WO2007/144639,2007,A1 .Location in patent: Page/Page column 44

3
[ 391-92-4 ]
[ 56874-97-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonia; In methanol; at 50℃; for 10h;Autoclave;	A mixture of <strong>[391-92-4]methyl 5-fluoro-2-hydroxybenzoate</strong> (22 g, 129 mmol) and methanolic ammonia (250 mL) was heated at 50 °C in an autoclave for 1 0 h. The reaction mixture was concentrated under reduced pressure, the resulting crude was codistilled with toluene and dried to give 5-fluoro-2- hydroxybenzamide as a brown solid (18.5 g, 92percent). LS-MS m/z: 1 54.0 (M-H). 1 H NMR (400 MHz, DMSO-d6): delta ppm 1 2.74 (s, 1 H), 8.40 (s, 1 H), 8.03 (s, 1 H), 7.73-7.71 (m, 1 H), 7.31 -7.29 (m, 1 H), 6.91 -6.90 (m, 1 H).
92%	With ammonia; In methanol; at 50℃; for 10h;Autoclave;	A mixture of <strong>[391-92-4]methyl 5-fluoro-2-hydroxybenzoate</strong> (22 g, 129 mmol)and methanolic ammonia (250 mL)was heated at 50°C in an autoclave for 10 h. The reaction mixture was concentrated under reducedpressure, the resulting crude was codistilled with toluene and dried to give 5-fluoro-2-hydroxybenzamide as a brown solid (1 8.5 g, 92percent yleld). LC-MS m/z 154.0 (M-H). 1H NMR (400 MHz, DMSO-d6) 6 ppm 12.74 (5, 1H), 8.40 (5, 1H), 8.03 (5, 1H), 7.73-7.71 (m, 1H), 7.31-7.29 (m, 1H), 6.91-6.90 (m, 1H).
	With ammonia; In methanol; at 60℃;	(a) 5-Fluoro-2-hydroxy-benzamide (193) To a screw tight 50 mL pressure vessel was added <strong>[391-92-4]methyl 5-fluoro-2-hydroxybenzoate</strong> (1.0 g, 5.88 mmol) and (7N) ammonia in methanol (15 ml). The pressure vessel was sealed and contents stirred over night at 60° C. The reaction was cooled to room temperature and the solution evapourated to dryness to afford white crystalline solid. Single peak in LC-MS (0.91 g, 100percent purity); m/z (LC-MS, ESP), RT=2.94 mins, (M+H) 156.

With ammonia; In water; at 50℃; for 60h;

5-Fluoro-2-hydroxybenzamide; Methyl 5-fluoro-2-hydroxybenzoate was dissolved in 37percent NH3/aq ( 2OmL) and stirred at 50°C for 60 hours. The solution was concentrated, diluted with ethylacetate (2OmL) and washed with brine. The product was used in the next step without any further purification. APCI-MS m/z: 156.0 [MH+].

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 678 - 681
[2]Patent: WO2016/96686,2016,A1 .Location in patent: Page/Page column 83-84
[3]Patent: WO2017/211759,2017,A1 .Location in patent: Page/Page column 46
[4]Patent: US2006/135770,2006,A1 .Location in patent: Page/Page column 35-36
[5]Patent: WO2006/46916,2006,A1 .Location in patent: Page/Page column 55

4
[ 891833-16-2 ]
[ 56874-97-6 ]
4-[5-(2-carbamoyl-4-fluoro-phenoxymethyl)-2-fluoro-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 1.0h;	(d) 4-[5-(2-Carbamoyl-4-fluoro-phenoxymethyl)-2-fluoro-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester (196) To a solution of 4-(2-fluoro-5-methanesulfonyloxymethyl-benzoyl)-piperazine-1-carboxylic acid tedt-butyl ester (195)(0.832 g, 2.0 mmol) in DMF (3mL) under a nitrogen blanket was added 5-fluoro-2-hydroxy-benzamide (193)(0.31 g, 2.0 mmol), followed by potassium carbonate (0.552 g, 4.0 mmol). The mixture was then heated to 90 C. After 1 hour of heating the reaction was cooled to 45 C. water (4 mL) was added. The reaction was then cooled to 0 C. with stirring. A fine white suspension resulted. The solid was filtered, washed with cold water (210 mL), hexane (210 mL) and TBME (2*10 ml). The dried solid provided single peak in LC-MS (0.548 g, 57% yield) and taken through to next step without need for any purification; m/z (LC-MS, ESP), RT=3.18 mins, (M+H) 476.

Reference： [1]Patent: US2006/135770,2006,A1 .Location in patent: Page/Page column 36

5
[ 345-16-4 ]
[ 56874-97-6 ]
[ 201530-82-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol;	a) 6-Fluoro-2-(5-fluoro-2-hydroxyphenyl)benz[e][1,3]oxazin4-one: 4.3 g of 5-fluoro-salicylamide and 4.7 g of 5-fluorosalicylic acid are boiled under reflux in 50 ml of xylene after addition of 0.3 ml of pyridine. 4.4 ml of thionyl chloride are added in the course of 2 h, the mixture is stirred for a further 1 h and the solvent is then distilled off under reduced pressure. The residue is suspended in 30 ml of ethanol, filtered off and washed with ethanol. After drying, 6-fluoro-2-(5-fluoro-2-hydroxyphenyl)benz[e][1,3]oxazin-4-one is obtained as slightly yellow crystals of m.p. 250-252 C.

Reference： [1]Patent: US6465504,2002,B1

6
[ 885266-19-3 ]
[ 56874-97-6 ]
5-fluoro-2-({(2S)-2-[(mesitylsulfonyl)amino]propyl}oxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Aryl ether formation: 5-Fluoro-2-({(2S)-2-[(mesitylsulfonyl)aminoJpropyl}oxy)benzamide; (2S)-2-[(Mesitylsulfonyl)amino]propyl 2,4,6-trimethylbenzenesulfonate (263mg, 0.6mmole) was added to a slurry containing Cs2CO3 (487mg, 1.5mmole) and 5-fluoro-2- hydroxybenzamide (app. lmmole) in 2.5mL DMF. The reaction mixture was stirred overnight in room teperature before it was diluted with ethylacetate (2OmL) and washed with IM HCl/aq. The organic layer was dried, concentrated and purified on HPLC-C18.1H NMR (299.946 MHz5 DMSO) δ 7.79 (d, J= 8.4 Hz, IH), 7.63 (s, 2H), 7.50 (dd, J= 9.5, 3.3 Hz, IH), 7.20 (ddd, J= 9.1, 7.7, 3.4 Hz, IH), 6.99 - 6.88 (m, 3H), 3.87 (d, J= 5.9 Hz, 2H), 3.56 - 3.45 (m, IH), 2.50 (s, 6H), 2.18 (s, 3H), 0.93 (d, J= 6.8 Hz, 3H) APCI-MS m/z: 395.2 [MH+].

Reference： [1]Patent: WO2006/46916,2006,A1 .Location in patent: Page/Page column 55

7
[ 960244-32-0 ]
[ 56874-97-6 ]
[ 960244-33-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3.0h;	(e) 4-{5-[1-(2-Carbamoyl-4-fluoro-phenoxy)-ethyl]-2-fluorobenzoyl}-piperazine-1-carboxylic acid Tert-Butyl Ester8; To a solution of 4-[5-(1-chloro-ethyl)-2-fluoro-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester (6) (0.36 g, 0.84 mmol) in DMF (10 ml) was added 5-fluoro-2-hydroxy-benzamide (7) (0.18 mg, 1.16 mmol) and potassium carbonate (0.32 g, 2.3 mmol). The mixture was then heated to 90 C. for 3 hours and then cooled to ambient temperature. The reaction was then diluted with water (15 ml) and extracted with ethyl acetate (2×10 ml). The combined organics were dried over magnesium sulfate, filtered and then concentrated in vacuo to afford a pale yellow solid. The material was subjected to flash chromatography (eluent: hexane/ethyl acetate, 1:2, Rf 0.3). A white solid (8) was isolated. Single peak in LC-MS analysis. (250 mg, 53% yield); m/z (LC-MS, ESP), RT=4.44 mins, (M+1) 490.0.

Reference： [1]Patent: US2009/181951,2009,A1 .Location in patent: Page/Page column 19

8
[ 78-84-2 ]
[ 56874-97-6 ]
6-fluoro-2-isopropyl-2H-benzo[e][1,3]oxazin-4(3H)-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 9749 - 9752

9
[ 78-84-2 ]
[ 56874-97-6 ]
[ 1263152-87-9 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 9749 - 9752

10
[ 345-16-4 ]
[ 56874-97-6 ]

Reference： [1]Patent: WO2016/96686,2016,A1
[2]Patent: WO2017/211759,2017,A1

11
[ 56874-97-6 ]
4-chloro-6-fluoro-2H-1,3-benzoxazin-2-one [ No CAS ]

Reference： [1]Patent: WO2016/96686,2016,A1
[2]Patent: WO2017/211759,2017,A1

12
[ 56874-97-6 ]
(±)-6-fluoro-4-({3-[4-(7-fluoroisoquinolin-1-yl)piperazin-1-yl]-2-hydroxypropyl}amino)-2H-1,3-benzoxazin-2-one [ No CAS ]

Reference： [1]Patent: WO2016/96686,2016,A1

13
[ 56874-97-6 ]
[ 530-62-1 ]
6-fluoro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In tetrahydrofuran; at 0 - 20℃; for 14.0h;	To a stirred solution of <strong>[56874-97-6]5-fluoro-2-hydroxybenzamide</strong> (8.0 g, 51 .6 mmol)in dry THF (80 mL), 1,1’-carbonyldiimidazole (10.9 g, 67.09 mmol)was added at 000. The mixture was stirred at room temperaturefor 14 h then was concentrated under reduced pressure. The resulting crude was treated with MeOH and washed with diethyl ether. The resulting white solid was dried and used in the next step without further purification (5.1 g, 55% yleld, white solid). LC-MS mlz 180.0 (M-H). 1H NMR (400 MHz, DMSO-d6) 6 ppm 12.19 (5, 1H), 7.68-7.67 (m, 2H),7.50-7.48 (m, 1H).
	In tetrahydrofuran; at 0 - 20℃; for 14.0h;	To a stirred solution of <strong>[56874-97-6]5-fluoro-2-hydroxybenzamide</strong> (8.0 g, 51 .6 mmol) in dry THF (80 mL), 1 ,1 '-carbonyldiimidazole (10.9 g, 67.09 mmol) was added at 0C. The mixture was stirred at room temperature for 14 h then was concentrated under reduced pressure. The resulting crude was treated with MeOH and washed with diethyl ether. The resulting white solid was dried and used in the next step without further purification (5.1 g, 55% white solid). LS- MS m/z: 180.0 (M-H): 1 H NMR (400 MHz, DMSO-d6): δ ppm 1 2.19 (s, 1 H), 7.68-7.67 (m, 2H), 7.50-7.48 (m, 1 H).

Reference： [1]Patent: WO2017/211759,2017,A1 .Location in patent: Page/Page column 46; 47
[2]Patent: WO2016/96686,2016,A1 .Location in patent: Page/Page column 84

14
[ 541-41-3 ]
[ 56874-97-6 ]
6-fluoro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 678 - 681

15
[ 541-41-3 ]
[ 56874-97-6 ]
ethyl (5-fluoro-2-hydroxybenzoyl)carbamate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 678 - 681

16
[ 56874-97-6 ]
tert-butyl 4-(3-((6-fluoro-2-oxo-2H-benzo[e][1,3]oxazin-4-yl)amino)-2-hydroxypropyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/211759,2017,A1

17
[ 1807-68-7 ]
[ 56874-97-6 ]
8-fluoro-3,3-dimethyl-3,4-dihydrodibenzo[b,d]furan-1(2H)-one [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 1673 - 1681

18
[ 345-16-4 ]
[ 56874-97-6 ]
[ 201530-57-6 ]

Reference： [1]ACS Chemical Biology,2019,vol. 14,p. 1737 - 1750

19
[ 345-16-4 ]
[ 56874-97-6 ]
5-fluoro-N-(5-fluoro-2-hydroxybenzoyl)-2-hydroxybenzamide [ No CAS ]

Reference： [1]ACS Chemical Biology,2019,vol. 14,p. 1737 - 1750

20
[ 56874-97-6 ]
(R)-6-fluoro-2-methyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 11470 - 11477

21
[ 108-24-7 ]
[ 56874-97-6 ]
2-carbamoyl-4-fluorophenyl acetate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 11470 - 11477

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P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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