[ CAS No. 114715-38-7 ] {[proInfo.proName]}

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2D 3D

Structure of 114715-38-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 114715-38-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 114715-38-7 ]

SDS Specification

Alternatived Products of [ 114715-38-7 ]

Product Details of [ 114715-38-7 ]

CAS No. :	114715-38-7	MDL No. :	MFCD00082766
Formula :	C₁₁H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	CH₂CH(NH₂)C₂H₄NCH₂C₆H₅	InChI Key :	HBVNLKQGRZPGRP-NSHDSACASA-N
M.W :	176.26	Pubchem ID :	1519353
Synonyms :

Calculated chemistry of [ 114715-38-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	58.04
TPSA :	29.26 ?2

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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	1.01
Log Po/w (WLOGP) :	0.69
Log Po/w (MLOGP) :	1.46
Log Po/w (SILICOS-IT) :	1.52
Consensus Log Po/w :	1.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.78
Solubility :	2.93 mg/ml ; 0.0166 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	10.8 mg/ml ; 0.0611 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.65
Solubility :	0.39 mg/ml ; 0.00221 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 114715-38-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 114715-38-7 ]

* 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 [ 114715-38-7 ]
Downstream synthetic route of [ 114715-38-7 ]

[ 114715-38-7 ] Synthesis Path-Upstream 1~1

1
[ 24424-99-5 ]
[ 114715-38-7 ]
[ 131852-53-4 ]

Yield	Reaction Conditions	Operation in experiment
94.1%	Stage #1: With sodium hydroxide In water at 50 - 60℃; Stage #2: for 3 h;	A 500 ml four-neck flask equipped with a stirrer, a thermometer, a Dimroth condenser, and a titration funnel was loaded with (S)-3-amino-1-benzylpyrrolidine 17.6 g (0.1 mole, optical purity 99.5percent/ee), water 158.7 g, and Cation DS (manufactured by Sanyo Chemical Industries, Ltd.) 0.2 g and the pH of the mixture was adjusted to be 11+/-0.5 with an aqueous 48percent sodium hydroxide solution. While the mixture being stirred at 50 to 60°C, di-tert-butyl dicarbonate (hereinafter abbreviated as DiBoc) 26.2 g (0.12 mole) was dropwise added for about 2 hours. During the time, the reaction solution was adjusted at pH 11+/-0.5 with an aqueous 48percent sodium hydroxide solution. After being stirred for further 1 hour, the reaction solution was cooled to a room temperature and precipitated crystal was separated by filtration. The crystal was vacuum dried at 50°C to obtain (S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine 26.0 g. The yield was 94.1percent and the chemical purity was 99.1 percent and an optical purity was 99.5percent ee. The same apparatus as that of Example 1 was loaded with (S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine 26.0 g (optical purity 99.5percent ee), water 120 g, and 5percent Pd/C 2.6 g (PE type, 55.27percent water content, manufactured by N. E. Chemcat Corp.) and the contents were stirred at reaction temperature of 40°C for 10 hours under hydrogen ventilation. When the reaction solution was analyzed by GC, and the peak of the raw material disappeared and other than toluene only 3-tert-butoxycarbonylaminopyrrolidine was detected. After completion of the reaction, Pd/C was removed by filtration and the filtrate was concentrated to 30 g by an evaporator. Next, the concentrated product was mixed with toluene and concentrated to 20 g to remove water by azeotropic boiling. While being mixed, the concentrated solution was mixed slowly with n-hexane 25 g to precipitate a crystal and further stirred for 2 hour in an ice bath. The precipitated crystal was separated by filtration and vacuum dried to obtain (S)-3-tert-butoxycarbonylaminopyrrolidine 15.4 g. The yield was 87.4percent, the chemical purity was 99.5 areapercent, and an optical purity was 99.5 percent ee. The water content was 0.4percent.

Reference： [1] Patent: EP1640364, 2006, A1, . Location in patent: Page/Page column 10-11
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826

[ 114715-38-7 ] Synthesis Path-Downstream 1~4

1
[ 131852-53-4 ]
[ 114715-38-7 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 3919 - 3926

2
[ 24424-99-5 ]
[ 114715-38-7 ]
[ 131852-53-4 ]

Yield	Reaction Conditions	Operation in experiment
94.1%		A 500 ml four-neck flask equipped with a stirrer, a thermometer, a Dimroth condenser, and a titration funnel was loaded with (S)-3-amino-1-benzylpyrrolidine 17.6 g (0.1 mole, optical purity 99.5%/ee), water 158.7 g, and Cation DS (manufactured by Sanyo Chemical Industries, Ltd.) 0.2 g and the pH of the mixture was adjusted to be 11+/-0.5 with an aqueous 48% sodium hydroxide solution. While the mixture being stirred at 50 to 60C, di-tert-butyl dicarbonate (hereinafter abbreviated as DiBoc) 26.2 g (0.12 mole) was dropwise added for about 2 hours. During the time, the reaction solution was adjusted at pH 11+/-0.5 with an aqueous 48% sodium hydroxide solution. After being stirred for further 1 hour, the reaction solution was cooled to a room temperature and precipitated crystal was separated by filtration. The crystal was vacuum dried at 50C to obtain (S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine 26.0 g. The yield was 94.1% and the chemical purity was 99.1 % and an optical purity was 99.5%ee. The same apparatus as that of Example 1 was loaded with (S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine 26.0 g (optical purity 99.5%ee), water 120 g, and 5% Pd/C 2.6 g (PE type, 55.27% water content, manufactured by N. E. Chemcat Corp.) and the contents were stirred at reaction temperature of 40C for 10 hours under hydrogen ventilation. When the reaction solution was analyzed by GC, and the peak of the raw material disappeared and other than toluene only 3-tert-butoxycarbonylaminopyrrolidine was detected. After completion of the reaction, Pd/C was removed by filtration and the filtrate was concentrated to 30 g by an evaporator. Next, the concentrated product was mixed with toluene and concentrated to 20 g to remove water by azeotropic boiling. While being mixed, the concentrated solution was mixed slowly with n-hexane 25 g to precipitate a crystal and further stirred for 2 hour in an ice bath. The precipitated crystal was separated by filtration and vacuum dried to obtain (S)-3-tert-butoxycarbonylaminopyrrolidine 15.4 g. The yield was 87.4%, the chemical purity was 99.5 area%, and an optical purity was 99.5 %ee. The water content was 0.4%.

Reference： [1]Patent: EP1640364,2006,A1 .Location in patent: Page/Page column 10-11
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 1815 - 1826

3
[ 114715-38-7 ]
[ 79286-79-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen; In methanol; at 70℃; under 7500.75 Torr; for 8h;	7.0 g of the (S)-1-benzyl-3-aminopyrrolidine, 25 ml of methanol, and 0.7 g of 5% Pd/C were introduced into a 100 ml autoclave, and hydrogen was adjusted to have a pressure of 1 MPa. The temperature was increased to 70 C. and stirring was performed for 8 hours. After the reaction was complete, the temperature was decreased to room temperature and the pressure was released. The content was filtered and the mother liquor was concentrated and distilled, and thus 3.2 g of (S)-3-aminopyrrolidine were obtained as the distillate collected at 80 to 83 C./40 kPa. As a result of analysis, the chemical purity was 99% and the optical purity was 90% e.e.
91%	With hydrogen;5% palladium over charcoal; In water; at 80℃; for 8h;	A 500 ml four-neck flask equipped with a stirrer, a thermometer, a Dimroth condenser, and a gas introduction pipe was loaded with (S)-3-amino-1-benzylpyrrolidine 52.5 g (0.3 mole, optical purity 99.5%/ee), water 97.5 g, and 5% Pd/C 5.25 g (PE type, 55.27% water content, manufactured by N. E. Chemcat Corp.), and while the contents being stirred at 80C, hydrogen was ventilated for 8 hours. After hydrogen ventilation was stopped, the mixture was cooled to a room temperature while being stirred and the catalyst was separated by vacuum filtration. The filtrate was vacuum concentrated to about 50 g by an evaporator. The concentrated product was distilled by a distillation apparatus equipped with about 5-step refining distillation towers packed with Heli-pack to obtain (S)-3-aminopyrraiidine 23.6 g as a fraction at 4.8 kPa. The yield was 91.0% and the chemical purity was 99.9 area% and an optical purity was 99.5%ee.

Reference： [1]Patent: US6348600,2002,B1 .Location in patent: Page column 14
[2]Patent: EP1640364,2006,A1 .Location in patent: Page/Page column 10
[3]Patent: EP1236716,2002,A1 .Location in patent: Example 6

4
[ 22123-14-4 ]
[ 114715-38-7 ]
[ 952444-06-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In diethylene glycol; at 140℃; for 2h;microwave reaction;	Reference Example 29: Synthesis of (S)-N-(1-benzylpyrrolidin-3-yl)-6-methyl-4-trifluoromethylpyridin-2-amine A mixture of <strong>[22123-14-4]2-chloro-6-methyl-4-trifluoromethylpyridine</strong> (0.196 g), (S)-1-benzyl-3-aminopyrrolidine (0.529 g), diethylene glycol (4 mL), and N,N-diisopropylethylamine (0.52 mL) was heated at 140C for 2 h using a microwave reaction apparatus. After completion of the reaction, water and ethyl acetate were added to the reaction solution, the mixture was extracted with ethyl acetate, washed with saturated brine, and then dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, and then the crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (silica gel, hexane/ethyl acetate = 5:1-2:1) to obtain (S)-N-(1-benzylpyrrolidin-3-yl)-6-methyl-4-trifluoromethylpyridin-2-amine (0.082 g). 1H-NMR (300 MHz, DMSO-d6): delta7.20-7.34 (m, 5H), 6.60 (s, 1H), 6.32 (s, 1H), 5.01 (d, J=8.00 Hz, 1H), 4.20-4.30 (m, 1H), 3.63 (d, J=5.8 Hz, 2H), 2.75-2.85 (m, 2H), 2.50-2.60 (m, 1H), 2.40 (s, 3H), 2.30-2.50 (m, 2H), 1.60-1.70 (m, 1H)

Reference： [1]Patent: EP2003131,2008,A1 .Location in patent: Page/Page column 77

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Technical Information

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Ghs Precautionary Statements

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Code	Phrase
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H402	Harmful to aquatic life
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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 114715-38-7 ] {[proInfo.proName]}

Quality Control of [ 114715-38-7 ]

Related Doc. of [ 114715-38-7 ]

Product Details of [ 114715-38-7 ]

Calculated chemistry of [ 114715-38-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 114715-38-7 ]

Application In Synthesis of [ 114715-38-7 ]

[ 114715-38-7 ] Synthesis Path-Upstream 1~1

[ 114715-38-7 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 114715-38-7 ]

Aryls

Amines

Related Parent Nucleus of [ 114715-38-7 ]

Aliphatic Heterocycles

Pyrrolidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 114715-38-7 ]

Related Parent Nucleus of
[ 114715-38-7 ]