[ CAS No. 362703-20-6 ] {[proInfo.proName]}

Name: 362703-20-6|Ethyl 1-(aminomethyl)cyclopropanecarboxylate hydrochloride|98%
Brand: Ambeed
SKU: A682920
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Quality Control of [ 362703-20-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 362703-20-6 ]

SDS Specification

Alternatived Products of [ 362703-20-6 ]

Product Details of [ 362703-20-6 ]

CAS No. :	362703-20-6	MDL No. :	MFCD18071250
Formula :	C₇H₁₄ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IWPIXNGIFMRSAU-UHFFFAOYSA-N
M.W :	179.64	Pubchem ID :	56773585
Synonyms :

Calculated chemistry of [ 362703-20-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.35
TPSA :	52.32 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) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.62
Log Po/w (WLOGP) :	1.03
Log Po/w (MLOGP) :	0.69
Log Po/w (SILICOS-IT) :	0.85
Consensus Log Po/w :	0.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.08
Solubility :	14.9 mg/ml ; 0.0831 mol/l
Class :	Very soluble
Log S (Ali) :	-1.29
Solubility :	9.14 mg/ml ; 0.0509 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.2
Solubility :	11.3 mg/ml ; 0.063 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 362703-20-6 ]

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 [ 362703-20-6 ]

* 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 [ 362703-20-6 ]

[ 362703-20-6 ] Synthesis Path-Downstream 1~8

1
[ 1558-81-2 ]
[ 362703-20-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogen;platinum(IV) oxide; In methanol; under 2585.81 Torr; for 2h;	A solution of <strong>[1558-81-2]1-cyano-cyclopropanecarboxylic acid ethyl ester</strong> (1.0 g, 7.18 mmol), concentrated hydrochloric acid (1.5 mL), and platinum oxide (0.20 g) in methanol (50 mL) was pressurized with 50 psi of hydrogen for 2 hr. The heterogeneous mixture was filtered through Celite and concentrated to give the desired amine as a hydrochloride salt (1.26 g, 97%). MS found: (M+H)+=144
	With hydrogenchloride; hydrogen;platinum(IV) oxide; In ethanol; under 2068.65 Torr; for 20h;	Concentrated hydrochloric acid (25 mL) and platinum oxide (0.98 g) were added to a solution of the material from Part A in ethanol (225 mL). The mixture was placed under hydrogen pressure (40 psi, 2.8 X lO5 Pa) on a Parr apparatus for 20 hours. The reaction mixture was filtered through a layer of CELITE filter aid. The filter cake was rinsed with methanol (200 mL). The filtrate was concentrated under reduced pressure. The residue was reconcentrated under reduced pressure three times from methanol and twice from toluene to provide 31.7 g of ethyl 1-aminomethylcyclopropionate hydrochloride
	With hydrogenchloride; hydrogen;platinum(IV) oxide; In ethanol; water; under 2068.65 Torr; for 20h;	Platinum (IV) oxide (0.98 g) and concentrated hydrochloric acid (25 mL) were added to a solution of the material from Part A in ethanol (225 mL), and the mixture was placed under hydrogen pressure (40 psi, 2.8*105 Pa) on a Parr apparatus and shaken for 20 hours and then filtered through a layer of CELITE filter agent. The filter cake was washed with methanol (200 mL), and the combined filtrates were concentrated under reduced pressure. The residue was three times dissolved in methanol and concentrated and then twice dissolved in toluene and concentrated to afford ethyl 1-(aminomethyl)cyclopropanecarboxylate hydrochloride as a thick, pale yellow oil.

Reference： [1]Patent: US2004/72802,2004,A1 .Location in patent: Page/Page column 45-46
[2]Patent: WO2006/28545,2006,A2 .Location in patent: Page/Page column 162
[3]Patent: US2007/219196,2007,A1 .Location in patent: Page/Page column 73-74

3
[ 362703-20-6 ]
[ 39061-97-7 ]
[ 866650-46-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 5 - 20℃;	92.C Triethylamine (41 mL, 294 mmol) was added to a suspension of 4-chloro-3- nitroquinoline (24.5 g, 118 mmol) in dichloromethane (250 mL). The mixture was cooled to 5 °C. A solution of the material from Part B in dichloromethane (200 mL) was added over a period of 15 minutes. The reaction mixture was stirred at 5 °C for 1 hour and then at ambient temperature overnight. The reaction mixture was washed with aqueous saturated sodium bicarbonate (250 mL). The aqueous layer was back extracted with dichloromethane (2 x 50 mL). The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide an orange oil. This material was recrystallized from acetonitrile to provide 21.47 g of ethyl l-[(3- nitroquinolin-4-ylamino)methyl]cyclopropionate as a bright yellow solid.
	With triethylamine In dichloromethane at 5 - 20℃; for 1.25h;	64.C A suspension of 4-chloro-3-nitroquinoline (24.5 g, 118 mmol) and triethylamine (41 mL, 294 mmol) in dichloromethane (450 mL) was cooled to 5° C., and a solution of the material from Part B in dichloromethane (200 mL) was added over a period of 15 minutes. The reaction was stirred at 5° C. for one hour, allowed to warm to ambient temperature, stirred overnight, and washed with saturated aqueous sodium bicarbonate (250 mL). The aqueous layer was extracted with dichloromethane (2*50 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting orange oil was recrystallized from acetonitrile to provide 21.47 g of ethyl 1-[(3-nitroquinolin-4-yl)amino]methyl}cyclopropanecarboxylate as a bright yellow solid.

Reference： [1]Current Patent Assignee: 3M CO - WO2006/28545, 2006, A2 Location in patent: Page/Page column 162-163
[2]Current Patent Assignee: 3M CO - US2007/219196, 2007, A1 Location in patent: Page/Page column 74

4
[ 362703-20-6 ]
[ 459-57-4 ]
[ 1086106-35-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: ethyl 1-(aminomethyl)cyclopropanecarboxylate hydrochloride; 4-fluorobenzaldehyde In methanol at 25℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In methanol at 25℃; for 18h; Stage #3: With sodium hydrogencarbonate In methanol; water	3 1-[(4-Fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid ethyl ester 1-[(4-Fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid ethyl ester A solution of (1-aminomethyl)-cyclopentyl-acetic acid methyl ester hydrochloride (626 mg, 4.37 mmol) in anhydrous methanol (20 mL) was treated with 4-fluoro-benzaldehyde (0.46 mL, 4.37 mmol) and stirred at 25° C. under a nitrogen environment. After 10 min, glacial acetic acid (0.83 mL, 14.5 mmol) and sodium triacetoxyborohydride (2.3 g, 10.9 mmol) were added sequentially, and the resulting mixture was stirred at 25° C. for 18 h. The reaction was diluted with a saturated aqueous sodium bicarbonate solution (30 mL) and extracted with ethyl acetate (3*50 mL). The combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give 1-[(4-fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid ethyl ester (870 mg, 79%) as a colorless oil. LC-MS (ESI) calculated for C14H18FNO2: 251.1, found 252.1 [M+H+].
79.2%	With sodium tris(acetoxy)borohydride; acetic acid In methanol at 0 - 20℃;	1-1.1 Step 1: Synthesis of 1-[(4-fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid ethyl ester (5) The above amino-acid ethyl ester hydrochloride (4) (625.8 mg, 4.37 mmol) was dissolved in MeOH (20 mL), the para-F-benzaldehyde (460 μL, 4.37 mmol) was added at room temperature followed by HOAc (830 μL) and Na(OAc)3BH (2.3 g, 10.93 mmol) portion-wise as solid at 0° C. (ice-H2O bath). The reaction mixture was stirred at room temperature overnight. The LC-MS analysis confirmed the completion of the reaction. Saturated aqueous NaHCO3 solution (30 mL) was added to neutralize the reaction (pH=8). The desired product was extracted out with EtOAc (50 mL*3) and the combined organic layers were washed with brine (25 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure at room temperature to give the crude product (5) (870.1 mg) in 79.2% yield. LC-MS (m/e): 252.1 [M+1]+ (exact ms: 251.13). This crude product was directly used in next step.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2009/62263, 2009, A1 Location in patent: Page/Page column 24
[2]Current Patent Assignee: ROCHE HOLDING AG - US2008/292588, 2008, A1 Location in patent: Page/Page column 27-28

5
[ 362703-20-6 ]
[ 1086106-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0 - 20 °C 2: tetrahydrofuran / 20 °C 3: sodium ethanolate / ethanol / 1 h / 20 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2008/292588, 2008, A1

6
[ 362703-20-6 ]
C₁₄H₁₄FNO₂ [ No CAS ]
[ 1086106-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0 - 20 °C 2: tetrahydrofuran / 20 °C 3: sodium ethanolate / ethanol / 1 h / 20 °C 4: pyridine / 4 h / 110 - 120 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2008/292588, 2008, A1

7
[ 362703-20-6 ]
[ 1086106-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0 - 20 °C 2: tetrahydrofuran / 20 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2008/292588, 2008, A1

8
[ 317829-98-4 ]
[ 362703-20-6 ]
C₂₅H₃₅N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 1-(aminomethyl)cyclopropanecarboxylate hydrochloride With triethylamine In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-benzyloxycarbonyl-4-(tert-butyloxycarbonyl)piperazine-2-carboxaldehyde In ethanol at 20℃; for 1.5h; Inert atmosphere;	Intermediate S3-1: 1-Benzyl 4-tert-butyl 2-((((1- (ethoxycarbonyl)cyclopropyl)methyl)amino)methyl) piperazine-1,4-dicarboxylate To a solution of ethyl 1-(aminomethyl)cyclopropanecarboxylate hydrochloride (2.04 g, 11.4 mmol) in ethanol (50 mL) was added triethylamine (1.15 g, 11.4 mmol) at room temperature. After stirred at room temperature under nitrogen atmosphere for 0.5 hour, a solution of 1- benzyl 4-tert-butyl 2-formylpiperazine-1,4-dicarboxylate S1-2 (3.10 g, 7.56 mmol) in ethanol (10 mL) was added and stirred at room temperature for 1.5 hours. Then sodium cyanoborohydride (1.12 g, 17.8 mmol) was added at 0 oC. After stirred at room temperature for 2 hours, the mixture was quenched with ice water (15 mL), then removed ethanol under vacuo. The residue was diluted with water (40 mL) and extracted with ethyl acetate (20 mL) for three times. The combined organic layers were dried over Na2SO4(s) and filtered. The filtrate was concentrated to give a residue, which was purified by C18 column (acetonitrile : water = 65 % to 95 %) to give the title compound (2.00 g, 50 % yield) as yellow oil. LC-MS (ESI): RT = 1767 min mass calcd for C25H37N3O6 4753 m/z found 4763 [M+H]+ 1H NMR (400 MHz, CDCl3) d 7.36 - 7.32 (m, 5H), 5.14 (s, 1H), 4.27 - 3.93 (m, 6H), 3.05 - 2.66 (m, 7H), 1.71 (br s, 1H), 1.46 (s, 9H), 1.23 - 1.19 (m, 5H), 0.81 - 0.68 (m, 2H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/255016, 2020, A1 Location in patent: Page/Page column 114-115

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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
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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
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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. 362703-20-6 ] {[proInfo.proName]}

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[ 362703-20-6 ] Synthesis Path-Downstream 1~8

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Aliphatic Cyclic Hydrocarbons

Esters

Amines

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[ 362703-20-6 ]