[ CAS No. 1256944-96-3 ] {[proInfo.proName]}

Name: 1256944-96-3|(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride|95%
Brand: Ambeed
SKU: A154055
Rating: 96 (32 reviews)

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2D 3D

Structure of 1256944-96-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1256944-96-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1256944-96-3 ]

SDS Specification

Alternatived Products of [ 1256944-96-3 ]

Product Details of [ 1256944-96-3 ]

CAS No. :	1256944-96-3	MDL No. :	MFCD16294081
Formula :	C₉H₁₃ClFNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HBJULLIYARHDSU-FYZOBXCZSA-N
M.W :	205.66	Pubchem ID :	53484667
Synonyms :

Calculated chemistry of [ 1256944-96-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.34
TPSA :	35.25 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) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.05
Log Po/w (WLOGP) :	2.75
Log Po/w (MLOGP) :	2.25
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	1.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.62
Solubility :	0.498 mg/ml ; 0.00242 mol/l
Class :	Soluble
Log S (Ali) :	-2.42
Solubility :	0.784 mg/ml ; 0.00381 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.274 mg/ml ; 0.00133 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 1256944-96-3 ]

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 [ 1256944-96-3 ]

* 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 [ 1256944-96-3 ]

[ 1256944-96-3 ] Synthesis Path-Downstream 1~7

1
[ 160678-35-3 ]
[ 1256944-96-3 ]
[ 1257106-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In N,N-dimethyl-formamide; at 20℃;	General procedure BTo a solution of ketone (1 eq.) in DMF (0.38M) were added the amine (1.1 eq.), glacial AcOH (1.2 eq.) and NaBH(OAc)3 (1.4 eq.). The mixture was stirred at r.t. overnight and filtered. Purification was performed by preparative HPLC-MS.; Preparation 33: Methyl 4-[(lR,3S)-3-[[(lR)-l-(4-fluoro-3-methoxy-phenyl)ethyl]- amino]cyclopentyl]benzoateGeneral procedure B was followed using methyl 4-[(lR)-3-oxocyclopentyl]benzoate (preparation 32) as the ketone and (lR)-l-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. The resulting isomers were separated by flash chromatography (gradient of 0-50% EtOAc in heptane containing 3% NEt3). The faster eluting peak was isolated to afford the title compound. IH NMR (300 MHz, DMSO) delta 7.86 (d, J = 8.3 Hz, 2H), 7.38 (d, J = 8.3 Hz, 2H), 7.15 (dd, J = 8.7, 1.8 Hz, IH), 7.09 (dd, J = 11.5, 8.3 Hz, IH), 6.91 - 6.85 (m, IH), 3.83 (2 s, 6H), 3.80 - 3.70 (m, IH), 3.05 - 2.86 (m, 2H), 2.22 - 1.52 (m, 5H), 1.41 - 1.27 (m, IH), 1.23 (d, J = 6.6 Hz, 3H).
	With sodium tris(acetoxy)borohydride; acetic acid; In N,N-dimethyl-formamide; at 20℃;	Intermediate 2: Methyl 4-[( lR,3S)-3-[[(lR)-l-(4-Fluoro-3-methoxy-phenyl)- ethyl]-amino]cyclopentyl]benzoateTo a solution of Intermediate 1 in DMF (0.38M) were added (lR)-l-(4-fluoro-3- methoxyphenyl)ethylamine hydrochloride (1.1 eq.), glacial AcOH (1.2 eq.) and NaBH(OAc)3 (1.4 eq.). The mixture was stirred at r.t. overnight and filtered. The resulting isomers were separated by flash chromatography (gradient of 0-50% EtOAc in heptane containing 3% Et3N). The faster eluting peak was isolated to afford the title compound 1H NMR (300 MHz, DMSO) delta 7.86 (d, J = 8.3 Hz, 2H), 7.38 (d, J = 8.3 Hz, 2H), 7.15 (dd, J = 8.7, 1.8 Hz, 1H), 7.09 (dd, J = 11.5, 8.3 Hz, 1H), 6.92 - 6.84 (m, 1H), 3.82 (2 s, 6H), 3.80 - 3.70 (m, 1H), 2.96 (dd, J = 19.0, 8.6 Hz, 2H), 2.22 - 2.02 (m, 2H), 2.01 - 1.52 (m, 4H), 1.41 - 1.27 (m, 1H), 1.23 (d, J = 6.6 Hz, 3H).

Reference： [1]Patent: WO2010/136037,2010,A1 .Location in patent: Page/Page column 51; 62-63
[2]Patent: WO2012/69421,2012,A1 .Location in patent: Page/Page column 28-29

2
[ 1257106-44-7 ]
[ 1256944-96-3 ]
[ 1379647-74-1 ]

Yield	Reaction Conditions	Operation in experiment
31%		Intermediate 2: Ethyl 2-[4-[( lR,3S)-3-[[( lR)-l-(4-fluoro-3-methoxy- phenyl)-ethyl]amino]cyclopentyl]phenoxy]acetateA solution of Intermediate 3 (2 g, 7.6 mmol) in acetonitrile (30 mL) was treated with (lR)-l-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride (1.56 g, 7.6 mmol), NaBH(OAc)3 (15.2 mmol) and AcOH (0.70 mL) and stirred overnight at rt. Sat.Na2C03 was added, and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgS04, and concentrated in vacuo. The residual oil was purified by flash chromatography (gradient of 20 - 80% EtAOc/1%2- propanol/0.5% Et3N in heptane/2.5% Et3N). The faster eluting isomer was collected to afford the title compound in 31% yield as an oil.XH NMR (300 MHz, DMSO) delta 7.18 - 7.04 (m, 4H), 6.87 (ddd, J = 8.2, 4.5, 2.0 Hz, 1H), 6.84 - 6.77 (m, 2H), 4.70 (s, 2H), 4.16 (q, J = 7.1 Hz, 2H), 3.82 (s, 3H), 3.75 (q, J = 6.5 Hz, 1H), 2.94 - 2.74 (m, 2H), 2.19 - 1.96 (m, 2H), 1.93 - 1.49 (m, 4H), 1.35 - 1.16 (m, 7H).

Reference： [1]Patent: WO2012/69419,2012,A1 .Location in patent: Page/Page column 29

3
[ 1256944-96-3 ]
[ 1379647-61-6 ]

Reference： [1]Patent: WO2012/69419,2012,A1

4
[ 1256944-96-3 ]
[ 1379647-73-0 ]

Reference： [1]Patent: WO2012/69419,2012,A1

5
[ 1256944-96-3 ]
[ 1379647-52-5 ]
[ 1379647-53-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	With NaBH(OAc)3; In acetonitrile; at 20℃; for 2h;	A solution of Intermediate 1 (3.25 mmol) in acetonitrile (4 mL) was treated with (lR)-l-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride (3.57 mmol) and NaBH(OAc)3 (4.87 mmol) for 2 h at rt. The reaction mixture was diluted with additional acetonitrile (10 mL) and loaded on silica gel. The two diastereomers were separated by flash chromatography (gradient of 0-50% of EtOAc in n-heptane). The title compound was obtained in 31% yield as the faster eluting isomer.*H NMR (300 MHz, CDCI3) delta 7.23 - 7.10 (m, 4H), 7.01 (dd, J = 11.1, 8.2 Hz, 2H), 6.82 (ddd, J = 8.1, 4.3, 1.9 Hz, 1H), 4.14 (q, J = 7.2 Hz, 2H), 3.91 (s, 3H), 3.85 (q, J = 6.1 Hz, 1H), 3.56 (s, 2H), 3.13 - 3.00 (m, 1H), 2.99 - 2.84 (m, 1H), 2.26 - 2.13 (m, 1H), 2.08 - 1.89 (m, 2H), 1.85 - 1.30 (m, 7H), 1.24 (d, J = 7.1 Hz, 3H).

Reference： [1]Patent: WO2012/69420,2012,A2 .Location in patent: Page/Page column 31

6
[ 1256944-96-3 ]
[ 1379584-59-4 ]
[ 1379584-62-9 ]

Yield	Reaction Conditions	Operation in experiment
22%		In a round-bottom flask Intermediate 1 (179 mg, 1.0 mmol) and (lR)-l-(4-fluoro- 3-methoxyphenyl)ethylamine hydrochloride (206 mg, 1.0 mmol) was suspended in CH3CN (4 mL), sodium triacetoxyborohydride (279 mg, 1.4 mmol) followed by acetic acid (60 mu) was added and the reaction mixture stirred at roomtemperature for 16h. Saturated NaHC03, aq (3 mL) was added and the product was extracted with CH2CI2. The combined organic phases were concentrated and purified by flash chromatography (eluent: 50-100% EtOAc in heptane) to yield the title compound : 72 mg (22%). 1H NMR (300 MHz, CDCI3) delta 8.03 (d, J = 2.4 Hz, 1H), 7.62 (td, J = 8.1, 2.6 Hz, 1H), 7.06 - 6.94 (m, 2H), 6.86 - 6.78 (m, 2H), 3.90 (s, 3H), 3.83 (q, J = 6.6 Hz, 1H), 3.16 - 3.02 (m, 1H), 3.02 - 2.87 (m, 1H), 2.27 - 2.14 (m, 1H), 2.11 - 1.92 (m, 2H), 1.81 - 1.56 (m, 2H), 1.42 - 1.31 (m, 4H).

Reference： [1]Patent: WO2012/69402,2012,A1 .Location in patent: Page/Page column 35-36

7
[ 1256944-96-3 ]
methyl 5-(2-formyl-5,6,7,8-tetrahydroquinolin-4-yl)-2-methylbenzoate [ No CAS ]
(R)-methyl 5-(2-(((1-(4-fluoro-3-methoxyphenyl)ethyl)amino)methyl)5,6,7,8-tetrahydroquinolin-4-yl)-2-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		Intermediate-37 (0.103 g, 0.333 mmol) was added to a solution of (R)-1-(naphthalen-1- yl)ethanamine (0.057 g, 0.333 mmol) in dichloroethane (3 ml) and resulting mixture was stined at 25 C for 5 hrs. The reaction mixture was allowed to 0 C and added sodium triacetoxyborohydride (0.106 g, 0.499 mmol) then allowed to 25 C and further maintained for 16 hours. TLC showed the reaction completion. The reaction mixture was diluted withwater (25 ml) and dichloromethane (25 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2 x 5 ml). The combined organic extract was washed with water (2 x 25 ml), brine (50 ml) and dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to get 1 .5g of the crude residue. This residue was purified by column chromatography over silica gel (100-200 mesh) with an isocratic elution of 35%ethyl acetate in petroleum ether to afford title compound (0. 12g, 78%) as off white solid.

Reference： [1]Patent: WO2017/37616,2017,A1 .Location in patent: Page/Page column 73; 74

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Ghs Precautionary Statements

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P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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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
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

[ CAS No. 1256944-96-3 ] {[proInfo.proName]}

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[ 1256944-96-3 ] Synthesis Path-Downstream 1~7

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Fluorinated Building Blocks

Aryls

Ethers

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[ 1256944-96-3 ]