[ CAS No. 1357923-33-1 ] {[proInfo.proName]}

Name: 1357923-33-1|2-(Azetidin-3-yl)propan-2-ol hydrochloride|95%
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SKU: A334827
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Quality Control of [ 1357923-33-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1357923-33-1 ]

SDS Specification

Alternatived Products of [ 1357923-33-1 ]

Product Details of [ 1357923-33-1 ]

CAS No. :	1357923-33-1	MDL No. :	MFCD22199153
Formula :	C₆H₁₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZDTIEZKFOLVALT-UHFFFAOYSA-N
M.W :	151.63	Pubchem ID :	53249203
Synonyms :

Calculated chemistry of [ 1357923-33-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.72
TPSA :	32.26 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) :	-6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.56
Log Po/w (WLOGP) :	0.4
Log Po/w (MLOGP) :	0.57
Log Po/w (SILICOS-IT) :	0.63
Consensus Log Po/w :	0.43

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.07
Solubility :	13.0 mg/ml ; 0.0857 mol/l
Class :	Very soluble
Log S (Ali) :	-0.81
Solubility :	23.5 mg/ml ; 0.155 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.72
Solubility :	28.7 mg/ml ; 0.189 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 1357923-33-1 ]

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 [ 1357923-33-1 ]

* 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 [ 1357923-33-1 ]
Downstream synthetic route of [ 1357923-33-1 ]

[ 1357923-33-1 ] Synthesis Path-Upstream 1~1

1
[ 1257293-79-0 ]
[ 1357923-33-1 ]

Yield	Reaction Conditions	Operation in experiment
71.8%	With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃;	Step B: 2-(Azetidin-3-yl)propan-2-ol hydrochloride. To a solution of tert-butyl 3-(2-hydroxypropan-2-yl)azetidine-l-carboxylate (0.87 g, 4.04 mmol) in DCM (15 mL) at 0°C was added 4 M HC1 in dioxane (8.08 mL, 16.16 mmol) dropwise. The reaction was stirred overnight at RT. The reaction mixture was concentrated and dried in vacuo to generate 2-(azetidin-3-yl)propan-2-ol hydrochloride as a brown solid (0.44 g, 71.8 percent yield).

Reference： [1] Patent: WO2012/18668, 2012, A1, . Location in patent: Page/Page column 255-256

[ 1357923-33-1 ] Synthesis Path-Downstream 1~8

1
[ 1357923-33-1 ]
(E)-4-fluoro-N-(6-(hydroxymethyl)-1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide [ No CAS ]
(E)-4-fluoro-N-(6-((3-(2-hydroxypropan-2-yl)azetidin-1-yl)methyl)-1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21.4%		Step C: (E)-4-Fluoro-N-(6-((3-(2-hydroxypropan-2-yl)azetidin-l- yl)methyl)-l-(cis-4-(isopropylcarbamoyl)cyclohexyl)-lH-benzo[d]imidazol-2(3H)- ylidene)benzamide. To a 0C cooled solution of (E)-4-fluoro-N-(6-(hydroxym ethyl)- 1- (cis-4-(isopropylcarbamoyl)cyclohexyl)-lH-benzo[d]imidazol-2(3H)-ylidene)benzamide (100 mg, 0.221 mmol) in DCM (5 mL) was added thionyl chloride (0.081 mL, 1.105 mmol) dropwise, and the reaction was stirred at 0C for 30 minutes. The solvent was removed on a rotovap, and the residue suspended in ACN (2 mL) and re-concentrated to remove residual thionyl chloride. The residue was resuspended in DMF (2 mL), cooled to 0C, and <strong>[1357923-33-1]2-(azetidin-3-yl)propan-2-ol hydrochloride</strong> (101 mg, 0.663 mmol) and DBU (0.10 mL, 0.663 mmol) were added. After stirring for 16 hours at RT, the reaction mixture was concentrated and purified by reverse-phase preparative HPLC, using 0.1 % TFA in ACN/water, (gradient 15% to 90%>). The product fractions were combined, neutralized with saturated aqueous NaHCC , and extracted with EtOAc (x2). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to provide (E)-4-fluoro-N-(6-((3-(2-hydroxypropan-2- yl)azetidin- 1 -yl)methyl)- 1 -(cis-4-(isopropylcarbamoyl)cyclohexyl)- 1 H-benzo[d]imidazol- 2(3H)-ylidene) as a white powder benzamide (26 mg, 21.4 % yield). MS, m/z (C31H40FN5O3): calcd, 549.3; found, 549.9 [M+H].

Reference： [1]Patent: WO2012/18668,2012,A1 .Location in patent: Page/Page column 256

2
[ 1257293-79-0 ]
[ 1357923-33-1 ]

Yield	Reaction Conditions	Operation in experiment
71.8%	With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20℃;	Step B: 2-(Azetidin-3-yl)propan-2-ol hydrochloride. To a solution of tert-butyl 3-(2-hydroxypropan-2-yl)azetidine-l-carboxylate (0.87 g, 4.04 mmol) in DCM (15 mL) at 0C was added 4 M HC1 in dioxane (8.08 mL, 16.16 mmol) dropwise. The reaction was stirred overnight at RT. The reaction mixture was concentrated and dried in vacuo to generate 2-(azetidin-3-yl)propan-2-ol hydrochloride as a brown solid (0.44 g, 71.8 % yield).

Reference： [1]Patent: WO2012/18668,2012,A1 .Location in patent: Page/Page column 255-256

3
[ 1357923-33-1 ]
C₂₅H₂₈ClFN₄O₂ [ No CAS ]
[ 1357921-05-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 6523 - 6540

4
[ 1357923-33-1 ]
[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate [ No CAS ]
C₂₂H₃₃N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 12h;	Example 96 A suspension of [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (100 mg), <strong>[1357923-33-1]2-(azetidin-3-yl)propan-2-ol hydrochloride</strong> (62 mg) and K2CO3 (94 mg) in DMF (1.0 mL) was stirred at 70 C. for 12 hours. The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/MeOH) to form a salt with 4 M HCl/EtOAc, and then washed with EtOAc to obtain 2-(1-[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}azetidin-3-yl)propan-2-ol hydrochloride (32 mg).

Reference： [1]Patent: US2015/111876,2015,A1 .Location in patent: Paragraph 0306

5
[ 1357923-33-1 ]
tert-butyl {(1R,3R)-1-[2-chloro-6-(difluoromethoxy)phenyl]-7-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-3-yl}carbamate [ No CAS ]
tert-butyl ((1R,3R)-1-(2-chloro-6-(difluoromethoxy)phenyl)-6-fluoro-7-(3-(2-hydroxypropan-2-yl)azetidin-1-yl)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In N,N-dimethyl-formamide; toluene; at 100℃; for 4h;Inert atmosphere; Microwave irradiation;	2-(Azetidin-3-yl)propan-2-ol hydrochloride (0.208 g, 1.37 mmol) and cesium carbonate(0.890 g, 2.74 mmol) were added to a solution of Intermediate 184 (0.500 g, 0.91 mmol) in a mixture of toluene/DMF (99/1, 15m1). The resulting mixture was purged with argon. (R/S)-(+/-)-2,2 ?-Bis(diphenylphosphino)- 1,1? -binaphthyl (0.018 g, 0.027 mmo 1) and tris(benzylideneacetone)dipalladium(0) (0.009 g, 0.009 mmo 1) were added. The reaction mixture was then heated in a microwave at 100C over 2 hours. As traces of the expectedazetidinyl derivative were detected by LCMS, a second addition of all reagents [2- (azetidin-3-yl)propan-2-ol hydrochloride (0.208 g, 1.37 mmol), cesium carbonate (0.890 g, 2.74 mmol), (R/S)-(+/-)-2,2 ?-Bis(diphenylphosphino)- 1,1 ?-binaphthyl (0.018 g, 0.027 mmol) and tris(benzylideneacetone)-dipalladium(0) (0.009 g, 0.009 mmol)] was carried out. The reaction mixture was then heated in microwave at 100C for a further 2 hours.Water (50 ml) was added and the resulting mixture was extracted with EtOAc (3x 50 ml). The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by Si02 flash chromatography with DCM/MeOH (100/0 to 95/5) as eluent to give the title compound (0.249 g, 47% yield).LCMS (Method 20, ES+) RT 1.09 mm., 581 [M+H].

Reference： [1]Patent: WO2016/50975,2016,A1 .Location in patent: Page/Page column 220; 221

6
C₁₀H₁₉NO₃ [ No CAS ]
[ 1357923-33-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride; In 1,4-dioxane; at 10 - 35℃; for 5h;	A mixture of compound 53-c (3.0 g, 14 mmol) and HC1 dioxane solution (4 M, 25 mE) was stirred at room temperature for S hrs. The reaction mixture was filtered, andthe filter cake was washed with dioxane, and dried undervacuum to yield compound 53-b (1.7 g, 81%), as a white solidHC1 salt. LC-MS (ESI): mlz=116.1 (M+H).

Reference： [1]Patent: US2016/214994,2016,A1 .Location in patent: Paragraph 0268; 0270

7
[ 1357923-33-1 ]
C₂₄H₃₂N₆O₅S₂ [ No CAS ]

Reference： [1]Patent: US2016/214994,2016,A1

8
potassium chloromethyltrifluoroborate [ No CAS ]
[ 1357923-33-1 ]
C₇H₁₄BF₃NO^(1-)*H⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		Compound 53-b HC1 salt (300 mg, 2.0 mmol), sodium hydroxide (100mg, 2.5 mmol), acetonitrile (15 mE) and water (3 mE) were added into a 50 mE round-bottomed flask, and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. A mixture of the residue, compound 1-f (310mg, 2.0 mmol), cyclopentyl methyl ether (CPME, 2.0 mE) and tert-amyl alcohol (0.7 mE) was sealed and heated to 1100 C., and stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was refluxed in 25 mE acetone for 1 hr, and filtered. The filtrate was concentrated under reduced pressure to yield compound 53-a (300 mg, 76%).

Reference： [1]Patent: US2016/214994,2016,A1 .Location in patent: Paragraph 0268; 0271

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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
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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. 1357923-33-1 ] {[proInfo.proName]}

Quality Control of [ 1357923-33-1 ]

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Product Details of [ 1357923-33-1 ]

Calculated chemistry of [ 1357923-33-1 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

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Application In Synthesis of [ 1357923-33-1 ]

[ 1357923-33-1 ] Synthesis Path-Upstream 1~1

[ 1357923-33-1 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 1357923-33-1 ]

Alcohols

Related Parent Nucleus of [ 1357923-33-1 ]

Aliphatic Heterocycles

Azetidines

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[ 1357923-33-1 ]

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[ 1357923-33-1 ]