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[ CAS No. 1001345-80-7 ]

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Chemical Structure| 1001345-80-7

Chemical Structure| 1001345-80-7

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Quality Control of [ 1001345-80-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1001345-80-7 ]

Product Details of [ 1001345-80-7 ]

CAS No. :	1001345-80-7	MDL No. :	MFCD26395470
Formula :	C₈H₆FNO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JXCYBTVSPGQRCM-UHFFFAOYSA-N
M.W :	215.14 g/mol	Pubchem ID :	57955614
Synonyms :

Calculated chemistry of [ 1001345-80-7 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.67
TPSA :	92.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.92
Log Po/w (XLOGP3) :	1.35
Log Po/w (WLOGP) :	1.86
Log Po/w (MLOGP) :	0.72
Log Po/w (SILICOS-IT) :	-0.45
Consensus Log Po/w :	0.88

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.12
Solubility :	1.62 mg/ml ; 0.00755 mol/l
Class :	Soluble
Log S (Ali) :	-2.89
Solubility :	0.276 mg/ml ; 0.00128 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.57
Solubility :	5.84 mg/ml ; 0.0272 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 1001345-80-7 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301-H311-H331	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1001345-80-7 ]

* 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 [ 1001345-80-7 ]
Downstream synthetic route of [ 1001345-80-7 ]

[ 1001345-80-7 ] Synthesis Path-Upstream 1~2

1
[ 1001345-80-7 ]
[ 1001346-91-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen; acetic acid In methanol at 20℃;	4-Amino-2-fluoro-5-methoxybenzoic acid: A solution of 2-fluoro-5-methoxy- 4-nitrobenzoic acid (10 g, 46 mmol), HOAc (50 mL) and MeOH (50 mL) was hydrogenated using a hydrogen balloon overnight. The solution was then filtered through celite and concentrated to a residue, which was triturated with ether and ethyl acetate. The solid was filtered and dried to give the product as light yellow powder (8.3 g, 98percent). ¹H NMR (400 MHz, DMSO-J₆) δ ppm 3.76 (s, 3 H) 5.88 (br s, 2 H) 6.36 (d, J= 16 Hz, 1 H) 7.13 (d, J= 8 Hz, 1 H) 12.32 (br s, 1 H). [M+H] calc'd for C₈H₈FNO₃, 186; found 186.
46%	With hydrogen In ethanol at 18 - 25℃; for 4 h;	2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 12; 7.76 g, 36.1 mmol) was stirred and dissolved in ethanol (200 mL) over 5percent Pd/C (770 mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46percent)¹H NMR (400.132 MHz, DMSO-d6) δ 3.78 (s, 3H), 5.84 (bs, 2H), 6.37 (d, 1H), 7.14 (d, 1H), 12.25 (bs, 1H).
46%	With hydrogen In ethanol at 18 - 25℃; for 4 h;	2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 28; 7.76g, 36.1mmol) was stirred and dissolved in ethanol (200 mL) over 5percent Pd/C (770mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46percent) ¹H NMR (400.132 MHz, DMSO-d6) δ 3.78 (s, 3H), 5.84 (bs, 2H), 6.37 (d, IH), 7.14 (d, IH), 12.25 (bs, IH).

46%

With hydrogen In ethanol at 18 - 25℃; for 4 h;

2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 28; 7.76g, 36.1mmol) was stirred and dissolved in ethanol (200 mL) over 5percent Pd/C (770mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46percent) ¹H NMR (400.132 MHz, DMSO-d6) δ 3.78 (s, 3H), 5.84 (bs, 2H), 6.37 (d, IH), 7.14 (d, IH), 12.25 (bs, IH).

Reference： [1] Patent: WO2009/42711, 2009, A1, . Location in patent: Page/Page column 266
[2] Patent: US2008/9482, 2008, A1, . Location in patent: Page/Page column 134
[3] Patent: WO2008/40951, 2008, A1, . Location in patent: Page/Page column 150
[4] Patent: WO2008/40951, 2008, A1, . Location in patent: Page/Page column 150
[5] Patent: WO2009/42711, 2009, A1, . Location in patent: Page/Page column 387-388
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 12, p. 3662 - 3666

2
[ 1001345-80-7 ]
[ 1137868-52-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 12, p. 3662 - 3666

[ 1001345-80-7 ] Synthesis Path-Downstream 1~6

1
[ 67-56-1 ]
[ 116465-48-6 ]
[ 1001345-80-7 ]

Yield	Reaction Conditions	Operation in experiment
98%		2,5-Difluoro-4-nitrobenzoic acid (Fluorochem; 100 mg, 0.43 mmol) and caesium carbonate (708 mg, 2.17 mmol) were taken up in dry DMF (2 mL) and dry methanol (120 uL, 2.88 mmol) was added and the reaction stirred at room temperature for 2 hrs. The reaction mixture was diluted with Ethyl Acetate (50 mL) and water (50 mL) and acidified to pH1 with 2N HCl solution. The organics were removed and the aqueous further extracted with Ethyl Acetate (2×50 mL). The combined organics were washed with water (50 mL), brine (50 mL), dried over MgSO4 and concentrated under reduced pressure to give the title compound as a yellow solid (91 mg, 0.42 mmol, 98%).1H NMR (399.902 MHz, CDCl3) delta 4.00 (s, 3H), 7.63 (d, 1H), 7.70 (d, 1H), 10.78 (br s, 1H);MS m/z 215.27 [M+H]+.
98%		2,5-Difluoro-4-nitrobenzoic acid (Fluorochem; 100 mg, 0.43 mmol) and caesium carbonate(708 mg, 2.17 mmol) were taken up in dry DMF (2 mL) and dry methanol (120 uL, 2.88 mmol) was added and the reaction stirred at room temperature for 2 hrs. The reaction mixture was diluted with Ethyl Acetate (50 mL) and water (50 mL) and acidified to pHl with 2N HCl <n="143"/>solution. The organics were removed and the aqueous further extracted with Ethyl Acetate (2 x 50 mL). The combined organics were washed with water (50 mL), brine (50 mL), dried over MgSO4 and concentrated under reduced pressure to give the title compound as a yellow solid (91 mg, 0.42 mmol, 98%). 1HNMR (399.902 MHz, CDC13) delta 4.00 (s, 3H), 7.63 (d, IH), 7.70 (d, IH), 10.78 (br s, IH); MS m/z 215.27 [M+H]+.
90%		Compound 168 :4-(9-Cyclopentyl-7,7-difiuoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-5-methoxy-N-(l- methylpiperidin-4-yl)benzamide; 2-Fluoro-5-methoxy-4-nitrobenzoic acid: To a solution of <strong>[116465-48-6]2,5-difluoro-4-nitrobenzoic acid</strong> (55 g, 291 mmol) in methanol (800 mL) at 80 0C was added a methanolic solution of potassium hydroxide (48.9 g, 873 mmol in 175 mL MeOH, pre-heated at 80 0C to dissolve) dropwise in a period of 2 h using an addition funnel. The reaction mixture was continuously stirred for 1 h after addition was completed. It was then concentrated, acidified with HCl to pH=l-2. The reaction mixture was then vigorously stirred overnight. Fine powder was filtered, washed with more water and dried to give the product as light yellow powder (55.4 g, 90%). 1H NMR (400 MHz, DMSO-J6) delta ppm 3.95 (s, 3 H) 7.66 (d, J= 4 Hz, 1 H) 8.01 (d, J= 8 Hz, 1 H). [M+H] calc'd for C8H6FNO5, 216; found 216.

With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3.5h;

To a suspension of <strong>[116465-48-6]2,5-difluoro-4-nitrobenzoic acid</strong> (2.46 mmol) and Cs2C03 (12.3 mmol) in DMF was added MeOH (16.5 mmol) and the mixture was stirred for 3h30 at RT. It was diluted with water, acidified with a 1 M solution of HCI until pH=1-2 and extracted three times with EtOAc. The organic phases were washed with brine, dried over MgS04 and concentrated in vacuo to give the title compound as light yellow solid. LC-MS (A): tR = 0.67 minH NMR ((CD3)2SO) <5: 13.96 (s br, 1 H), 8.03 (d, J = 9.6 Hz, 1 H), 7.68 (d, J = 5.8 Hz, 1 H), 3.97 (s, 3 H)

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 108
[2]Patent: WO2008/40951,2008,A1 .Location in patent: Page/Page column 141-142; 151
[3]Patent: WO2009/42711,2009,A1 .Location in patent: Page/Page column 413
[4]Patent: WO2014/97140,2014,A1 .Location in patent: Page/Page column 102; 103

2
[ 1001345-80-7 ]
[ 1001346-91-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen; acetic acid;palladium on activated charcoal; In methanol; at 20℃;Product distribution / selectivity;	4-Amino-2-fluoro-5-methoxybenzoic acid: A solution of 2-fluoro-5-methoxy- 4-nitrobenzoic acid (10 g, 46 mmol), HOAc (50 mL) and MeOH (50 mL) was hydrogenated using a hydrogen balloon overnight. The solution was then filtered through celite and concentrated to a residue, which was triturated with ether and ethyl acetate. The solid was filtered and dried to give the product as light yellow powder (8.3 g, 98%). 1H NMR (400 MHz, DMSO-J6) delta ppm 3.76 (s, 3 H) 5.88 (br s, 2 H) 6.36 (d, J= 16 Hz, 1 H) 7.13 (d, J= 8 Hz, 1 H) 12.32 (br s, 1 H). [M+H] calc'd for C8H8FNO3, 186; found 186.
46%	With hydrogen;5%-palladium/activated carbon; In ethanol; at 18 - 25℃; for 4h;	2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 12; 7.76 g, 36.1 mmol) was stirred and dissolved in ethanol (200 mL) over 5% Pd/C (770 mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46%)1H NMR (400.132 MHz, DMSO-d6) delta 3.78 (s, 3H), 5.84 (bs, 2H), 6.37 (d, 1H), 7.14 (d, 1H), 12.25 (bs, 1H).
46%	With hydrogen;5%-palladium/activated carbon; In ethanol; at 18 - 25℃; for 4h;	2-fluoro-5-methoxy-4-nitrobenzoic acid (Intermediate 28; 7.76g, 36.1mmol) was stirred and dissolved in ethanol (200 mL) over 5% Pd/C (770mg) and hydrogenated at ambient temperature for 4 hours. During this time product precipitated in the reaction. DMF (20 mL) was added to give a solution. The catalyst was filtered off and washed with EtOH and the solvent evaporated. The residue was triturated with diethyl ether to yield the title compound as a dark brown solid (3.06 g, 46%) 1H NMR (400.132 MHz, DMSO-d6) delta 3.78 (s, 3H), 5.84 (bs, 2H), 6.37 (d, IH), 7.14 (d, IH), 12.25 (bs, IH).

With H-cube hydrogenator;acetic acid; In methanol; at 20℃;Product distribution / selectivity;

4-Amino-2-fluoro-5-methoxybenzoic acid: A solution of ethyl 2-fluoro-5- methoxy-4-nitrobenzoic acid (217 mg, 1 mmol), HOAc (cat.) and MeOH (10 mL) was hydrogenated using H-cube hydrogenator. The solution was then concentrated and dried to give the product which can be used for next step without further purification. 1H NMR <n="389"/>(400 MHz, DMSO-J6) delta ppm 3.76 (s, 3 H) 5.88 (br s, 2 H) 6.36 (d, J= 16 Hz, 1 H) 7.13 (d, J= 8 Hz, 1 H) 12.32 (br s, 1 H).

Reference： [1]Patent: WO2009/42711,2009,A1 .Location in patent: Page/Page column 266
[2]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 134
[3]Patent: WO2008/40951,2008,A1 .Location in patent: Page/Page column 150
[4]Patent: WO2009/42711,2009,A1 .Location in patent: Page/Page column 387-388
[5]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3662 - 3666

3
[ 67-56-1 ]
[ 924868-81-5 ]
[ 124-41-4 ]
[ 1001345-80-7 ]

Yield	Reaction Conditions	Operation in experiment
70%		Compound 142: 4-(9-Cyclopentyl-7,7-difiuoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-5-methoxy-N-(l- methylpiperidin-4-yl)benzamide; [0622] 2-Fluoro-5-methoxy-4-nitrobenzoic acid: To a solution of methyl-2,5-difluoro- 4-nitrobenzoate (1 g, 4.6 mmol) in methanol (10 mL) was added sodium methoxide (95%, 393 mg, 6.9 mmol). The reaction mixture was stirred at room temperature overnight. It was then concentrated, acidified with HCl. Solid was filtered and dried to give the product as light yellow powder (728 mg, 70%). 1H NMR (400 MHz, DMSO-J6) delta ppm 3.95 (s, 3 H) 7.66 (d, J= 4 Hz, 1 H) 8.01 (d, J= 8 Hz, 1 H).

Reference： [1]Patent: WO2009/42711,2009,A1 .Location in patent: Page/Page column 387

4
[ 67-56-1 ]
[ 924868-81-5 ]
[ 1001345-80-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		Compound 31 : 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid; [0423] 2-Fluoro-5-methoxy-4-nitrobenzoic acid: To a solution of methyl-2,5-difluoro- 4-nitrobenzoate (10 g, 46 mmol) in methanol (100 mL) was added potassium hydroxide (7.73 g, 184 mmol) in two batches. The reaction mixture was stirred in an oil bath at 80 0C for 1 h. It was then concentrated, acidified with HCl. Solid was filtered, washed with water and dried to give the product as light yellow powder (10 g, quantitative yield). 1H NMR (400 MHz, DMSO-J6) delta ppm 3.95 (s, 3 H) 7.66 (d, J= 4 Hz, 1 H) 8.01 (d, J= 8 Hz, 1 H). [M+H] calc'd for C8H6FNO5, 216; found 216.

Reference： [1]Patent: WO2009/42711,2009,A1 .Location in patent: Page/Page column 266

5
[ 924868-81-5 ]
[ 1001345-80-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3662 - 3666

6
[ 1001345-80-7 ]
[ 1137868-52-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3662 - 3666

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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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