[ CAS No. 1246509-67-0 ] {[proInfo.proName]}

Name: 1246509-67-0|(R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride|97%
Brand: Ambeed
SKU: A185334
Rating: 97 (35 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 1246509-67-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1246509-67-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1246509-67-0 ]

SDS Specification

Alternatived Products of [ 1246509-67-0 ]

Product Details of [ 1246509-67-0 ]

CAS No. :	1246509-67-0	MDL No. :	MFCD22392685
Formula :	C₃₆H₁₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RSENWQHYPMZMBK-HNCPQSOCSA-N
M.W :	227.69	Pubchem ID :	66700566
Synonyms :

Calculated chemistry of [ 1246509-67-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	60.02
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) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.86
Log Po/w (WLOGP) :	1.9
Log Po/w (MLOGP) :	1.85
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	1.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.589 mg/ml ; 0.00259 mol/l
Class :	Soluble
Log S (Ali) :	-2.58
Solubility :	0.599 mg/ml ; 0.00263 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.437 mg/ml ; 0.00192 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 1246509-67-0 ]

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

Application In Synthesis of [ 1246509-67-0 ]

* 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 [ 1246509-67-0 ]

[ 1246509-67-0 ] Synthesis Path-Downstream 1~15

1
(3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride [ No CAS ]
[ 2471-70-7 ]
[ 1246505-96-3 ]

Yield	Reaction Conditions	Operation in experiment
83%		Synthesis of amino acid ester B-10: (R)-Methyl 3-(6-methoxy-2-naphthamido)-2,3-dihydro-1H-indene-5-carboxylate (B-10) N-Ethyl-diisopropylamine (3 eq.) was added to an ice-cold solution of <strong>[2471-70-7]6-methoxy-2-naphthoic acid</strong> (1 eq.) in methylene chloride. The reaction mixture was cooled to 0 C. and N-ethyl-N'-3-(dimethylamino)-propyl-carbodiimide hydrochloride (1.2 eq.) and 1-hydroxybenzotriazole hydrate (0.2 eq.) were then added. The mixture was stirred at this temperature for 15 min, before (3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-03 HCl) (0.989 mmol, 1 eq.) was added. The reaction mixture was then stirred at room temperature overnight. The mixture was diluted with ethyl acetate and the organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica, cyclohexane/ethyl acetate 2:1) to obtain the desired compound (B-10). Yield: 83%

Reference： [1]Patent: US2010/249095,2010,A1 .Location in patent: Page/Page column 88

2
[ 1246509-67-0 ]
[ 879-18-5 ]
[ 1365150-33-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 1.5h;Inert atmosphere;	(R)-Methyl 3-(1-naphthamido)-2,3-dihydro-1H-indene-5-carboxylate (B-36) (3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (1.098 mmol, 1 eq) was dissolved in dichloromethane, and DIPEA (2.5 eq) and naphthalene-1-carboxylic acid chloride (1.0 eq) were added under a protecting gas atmosphere at 0 C. The reaction mixture was stirred for 1.5 h at RT. Then the reaction mixture was diluted with ethyl acetate, washed 1* with 10% ammonium chloride solution and 1* with sat. NaCl solution, dried over magnesium sulfate and purified by column chromatography (silica gel, cyclohexane:ethyl acetate 3:1). Yield: 58%

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 86

3
[ 1246509-67-0 ]
[ 879-18-5 ]
[ 1365152-09-5 ]

Reference： [1]Patent: US2012/71461,2012,A1

4
[ 1246509-67-0 ]
[ 609-65-4 ]
[ 1246505-91-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere;	Method 1 (3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (8.784 mmol, 1 eq) was dissolved in dichloromethane, and triethylamine (3 eq) and 2-chlorobenzoic acid chloride (1.2 eq) were added at 0 C. under a protecting gas atmosphere. The reaction mixture was stirred for 1 h at RT. Then the reaction mixture was diluted with sat. NaHCO3 solution and the aqueous phase was extracted with dichloromethane (3*50 ml). The organic phase was dried over sodium sulfate and concentrated to yield (3R)-3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester (B-01). Yield: 98% or

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 82

5
[ 1246509-67-0 ]
[ 349-88-2 ]
[ 1365151-45-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 16h;	(R)-Methyl 3-(4-fluorophenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (C-04) DIPEA (447 mul, 2.634 mmol, 3 eq) was added at 0 C. to a solution of <strong>[1246509-67-0](3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride</strong> (A-01) (0.878 mmol, 1 eq) in dichloromethane (10 ml). A solution of 4-fluorobenzene-1-sulfonyl chloride (170 mg, 0.878 mmol, 1 eq) dissolved in dichloromethane (6 ml) was added dropwise and the mixture was stirred for 16 h at RT. After monitoring by thin-layer chromatography. the reaction solution was concentrated under reduced pressure and the residue was taken up in ethyl acetate, washed with 10% ammonium chloride solution, sodium hydrogen carbonate solution and sat. NaCl solution (in each case 1x), dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, ethyl acetate:cyclohexane 1:5). Yield: 88%

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 88

6
[ 482578-63-2 ]
[ 1246509-67-0 ]
[ 1246506-54-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine; In toluene; for 16h;Reflux;	(R)-Methyl 3-(7-chloro-1-oxoisoindolin-2-yl)-2,3-dihydro-1H-indene-5-carboxylate (D-01) (3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (1.757 mmol, 1 eq) was added to a solution of <strong>[482578-63-2]2-bromomethyl-6-chlorobenzoic acid methyl ester</strong> (1 eq) in toluene (5.4 ml) and triethylamine (2.1 eq). The reaction mixture was refluxed for 16 h. Then sat. NaHCO3 solution (20 ml) and ethyl acetate (50 ml) were added to the mixture and the phases were separated. The organic phase was extracted with 0.05 N HCl solution and sat. NaCl solution and dried over MgSO4. Concentration of the organic phase yielded the crude product, which was purified by column chromatography (ethyl acetate:cyclohexane, 3:1). The desired product (R)-methyl 3-(7-chloro-1-oxoisoindolin-2-yl)-2,3-dihydro-1H-indene-5-carboxylate (D-01) was thus obtained. Yield: 72%

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 88-89

7
[ 482578-63-2 ]
[ 1246509-67-0 ]
[ 1246507-38-9 ]

Reference： [1]Patent: US2012/71461,2012,A1

8
[ 1246509-67-0 ]
[ 21900-57-2 ]
[ 1246506-26-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	(R)-Methyl 3-(2-chloro-3-fluorobenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-32) (3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (0.2 mmol, 1 eq) was dissolved in dichloromethane, and DIPEA (2.5 eq) and 2-chloro-3-fluorobenzoic acid chloride (1.2 eq) were added under a protecting gas atmosphere at 0 C. The reaction mixture was stirred for 2 h at RT. Then the reaction mixture was diluted with ethyl acetate, washed 1* with sat. NaHCO3 solution, 1* with 10% ammonium chloride solution and 1* with sat. NaCl solution, dried over magnesium sulfate and purified by column chromatography (silica gel, cyclohexane:ethyl acetate 4:1). Yield: 92%

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 85-86

9
[ 3302-06-5 ]
[ 1246509-67-0 ]
[ 1365151-11-6 ]

Yield	Reaction Conditions	Operation in experiment
87%		(3R)-Methyl 3-(3,4-dimethylpentanamido)-2,3-dihydro-1H-indene-5-carboxylate (B-83) HATU (0.872 g, 2.3 mmol, 1 eq) and TEA (0.647 ml, 4.6 mmol, 2 eq) were added to an ice-cooled solution of 3,4-dimethylpentanoic acid (300 mg, 2.3 mmol, 1 eq) in THF (26 ml), and stirring was carried out for 15 min. (3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (0.786 g, 3.5 mmol, 1.5 eq) was added to the reaction solution, and the mixture was then stirred overnight at RT. The reaction solution was diluted with ethyl acetate, washed with sat. sodium hydrogen carbonate solution and sat. NaCl solution, dried over magnesium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, cyclohexane:ethyl acetate 2:1), the desired product was obtained. Yield: 87% (0.61 g)

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 87

10
[ 1246509-67-0 ]
[ 25940-35-6 ]
[ 1365149-91-2 ]

Yield	Reaction Conditions	Operation in experiment
85%		(R)-Methyl 3-(pyrazolo[1,5-a]pyrimidine-3-carboxamido)-2,3-dihydro-1H-indene-5-carboxylate (B-07) Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.25 g, 1.533 mmol, 1 eq) was dissolved in dichloromethane (20 ml), and the mixture was cooled to 0 C. Then DIPEA (0.65 ml, 2.833 mmol, 2.5 eq), EDCI (0.34 g, 1.84 mmol, 1.2 eq) and HOBT (29 mg, 0.307 mmol, 0.2 eq) were added in succession and stirring was carried out for 15 min at RT. The reaction solution was cooled to 0 C. again, <strong>[1246509-67-0](3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride</strong> (A-01) (0.34 g, 1.533 mmol, 1 eq), dissolved in dichloromethane (10 ml), was added, and the mixture was stirred for 16 h at RT. After monitoring by thin-layer chromatography, the reaction solution was diluted with ethyl acetate, washed in succession with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution (in each case 20 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate:cyclohexane 2:1) and the desired product (R)-methyl 3-(pyrazolo[1,5-a]pyrimidine-3-carboxamido)-2,3-dihydro-1H-indene-5-carboxylate (B-07) was thus obtained. Yield: 85%

Reference： [1]Patent: US2012/71461,2012,A1 .Location in patent: Page/Page column 83-84

11
[ 1246509-67-0 ]
[ 1246506-61-5 ]

Reference： [1]Patent: US2012/71461,2012,A1

12
[ 1246509-67-0 ]
[ 1365135-35-8 ]

Reference： [1]Patent: US2012/71461,2012,A1

13
[ 1246509-67-0 ]
[ 1365563-49-0 ]

Reference： [1]Patent: US2012/71461,2012,A1

14
[ 1246509-67-0 ]
[ 1365563-52-5 ]

Reference： [1]Patent: US2012/71461,2012,A1

15
[ 1246509-67-0 ]
[ 1365139-25-8 ]

Reference： [1]Patent: US2012/71461,2012,A1

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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Response
Code	Phrase
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P304	IF INHALED:
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P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
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P401
P402	Store in a dry place.
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P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
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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. 1246509-67-0 ] {[proInfo.proName]}

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[ 1246509-67-0 ] Synthesis Path-Downstream 1~15

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Esters

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