[ CAS No. 288315-03-7 ] {[proInfo.proName]}

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Quality Control of [ 288315-03-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 288315-03-7 ]

SDS Specification

Alternatived Products of [ 288315-03-7 ]

Product Details of [ 288315-03-7 ]

CAS No. :	288315-03-7	MDL No. :	MFCD05663714
Formula :	C₃H₆ClF₂N	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	CDBAEFXTCRKJPZ-UHFFFAOYSA-N
M.W :	129.54	Pubchem ID :	2758247
Synonyms :		Chemical Name :	3,3-Difluoroazetidine hydrochloride

Calculated chemistry of [ 288315-03-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	28.24
TPSA :	12.03 ?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) :	-6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.04
Log Po/w (WLOGP) :	1.49
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	1.59
Consensus Log Po/w :	0.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.3
Solubility :	6.52 mg/ml ; 0.0503 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	17.0 mg/ml ; 0.131 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.22
Solubility :	7.86 mg/ml ; 0.0607 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 288315-03-7 ]

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

Application In Synthesis of [ 288315-03-7 ]

* 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 [ 288315-03-7 ]
Downstream synthetic route of [ 288315-03-7 ]

[ 288315-03-7 ] Synthesis Path-Upstream 1~1

1
[ 288315-03-7 ]
[ 79099-07-3 ]
[ 1093066-74-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: at 20℃; for 0.25 h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 17 h;	To a solution of 4-oxo-piperidine-l-carboxylic acid tert-butyl ester (1.0 g, 5.0 mmol) in DCE (50 mL) was added 3,3-difluoroazetidine hydrochloride (712 mg, 5.5 mmol). The mixture was stirred at RT for 15 min, then sodium triacetoxyborohydride (1.59 g, 7.5 mmol) was added and stirring was continued for 17 h. The reaction mixture was diluted with brine and extracted with DCM. The organic layer was separated, dried (Na₂SO₄) and concentrated in vacuo. The resultant residue was purified by column chromatography to give 4-(3,3- difluoroazetidin-l-yl)-piperidine-l-carboxylic acid tert-butyl ester as a pale yellow solid (1.2 g, 88 percent). To a solution of 4-(3,3-difluoro-azetidin-l-yl)-piperidine-l-carboxylic acid tert- butyl ester (552 mg, 2.0 mmol) in DCM (4 mL) was added TFA (2 mL) and the resulting mixture was stirred at RT for 45 min. The reaction mixture was loaded onto an Isolute.(R). SCX- 2 cartridge. The cartridge was washed with MeOH then eluted with 2 M NH₃ in MeOH to give the title compound as a pale yellow solid (271 mg, 77 percent). <n="94"/>¹H NMR (400 MHz, CDCl₃): δ 1.16-1.27 (m, 2 H), 1.63-1.72 (m, 2 H), 2.14-2.23 (m, 1 H), 2.54-2.62 (m, 2 H), 3.09 (dt, J = 12.7, 3.9 Hz, 2 H) and 3.46-3.57 (m, 4 H).
88%	Stage #1: at 20℃; for 0.25 h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 17 h;	Reference Example 254-(3,3-Difluoro-azetidin-l-yl)-piperidineTo a solution of 4-oxo-piperidine-l-carboxylic acid tert-butyl ester (1.0 g, 5.0 mmol) in DCE (50 mL) was added 3,3-difluoroazetidine hydrochloride (712 mg, 5.5 mmol). The mixture was stirred at RT for 15 min, then sodium triacetoxyborohydride (1.59 g, 7.5 mmol) was added and stirring was continued for 17 h. The reaction mixture was diluted with brine and extracted with DCM. The organic layer was separated, dried (Na₂SO₄) and concentrated in vacuo. The resultant residue was purified by column chromatography to give 4-(3,3- difluoro-azetidin-l-yl)-piperidine-l-carboxylic acid tert-butyl ester as a pale yellow solid (1.2 g, 88 percent). To a solution of 4-(3,3-difluoro-azetidin-l-yl)-piperidine-l-carboxylic acid tert- butyl ester (552 mg, 2.0 mmol) in DCM (4 mL) was added TFA (2 mL) and the resulting <n="69"/>mixture was stirred at RT for 45 min. The reaction mixture was loaded onto an Isolute.(R). SCX- 2 cartridge, washed with MeOH then eluted with 2 M NH₃ in MeOH to give the title compound as a pale yellow solid (271 mg, 77 percent).¹H NMR (400 MHz, CDCl₃): δ 1.16-1.27 (m, 2 H), 1.63-1.72 (m, 2 H), 2.14-2.23 (m, 1 H), 2.54-2.62 (m, 2 H), 3.09 (dt, J = 12.7, 3.9 Hz, 2 H) and 3.46-3.57 (m, 4 H).
88%	at 20℃; for 17 h;	To a solution of 4-oxo-piperidine-l-carboxylic acid tert-butyl ester (1.0 g, 5.0 mmol) in DCE (50 mL) was added 3,3-difluoroazetidine hydrochloride (712 mg, 5.5 mmol). The mixture was stirred at RT for 15 min, then sodium triacetoxyborohydride (1.59 g, 7.5 mmol) was added and stirring was continued for 17 h. The reaction mixture was diluted with brine and extracted with DCM. The organic layer was separated, dried (Na₂SO₄) and concentrated in vacuo. The resultant residue was purified by column chromatography to give 4-(3,3- difluoroazetidin-l-yl)piperidine-l-carboxylic acid tert-butyl ester as a pale yellow solid (1.2 g, 88 percent). To a solution of 4-(3,3-difluoroazetidin-l-yl)piperidine-l-carboxylic acid tert-butyl ester (552 mg, 2.0 mmol) in DCM (4 mL) was added TFA (2 mL) and the resulting mixture was stirred at RT for 45 min. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge, washed with MeOH then eluted with 2 M NH₃ in MeOH to give the title compound as a pale yellow solid (271 mg, 77 percent). ₆¹H NMR (400 MHz, CDCl₃): 5 1.16-1.27 (m, 2 H), 1.63-1.72 (m, 2 H), 2.14-2.23 (m, 1 H), 2.54-2.62 (m, 2 H), 3.09 (dt, J = 12.7, 3.9 Hz, 2 H) and 3.46-3.57 (m, 4 H).

43%

Stage #1: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 16 h;
Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In N,N-dimethyl-formamide at 40℃; for 16 h;

A solution of 3,3-difluoroazetidine hydrochloride (300 mg, 2.3 mmol), te/f-butyl 4-oxopiperidine- 1 -carboxylate (461 mg, 2.3 mmol) and DIPEA (0.40 ml_, 2.3 mmol) in DMF (6 mL) was heated to 50 °C for 16 h before cooling to rt, addition of sodium triacetoxyborohydride (1 .23 g, 5.8 mmol) and AcOH (0.13 mL, 2.3 mmol) and further heating at 40 °C for 16 h. The mixture was cooled to rt, quenched by addition of sat. aq. NaHC0₃ (3 mL) and concentrated in vacuo. The residue was diluted with DCM (15 mL) and washed with sat. aq. NaHC0₃ (15 mL) and brine (15 mL). Organics were dried (Biotage phase separator) and concentrated in vacuo. The crude residue was purified on silica (Biotage Isolera, SNAP 25 g cartridge, 0 - 10 percent MeOH / DCM and subsequently SNAP 25 g cartridge, 0 - 5 percent MeOH / DCM) to yield te/f-butyl 4-(3,3- difluoroazetidin-1 -yl)piperidine-1 -carboxylate (273 mg, 43 percent) as a white crystalline solid, which was used directly in the next step.

Reference： [1] Patent: WO2009/53715, 2009, A1, . Location in patent: Page/Page column 92-93
[2] Patent: WO2009/53716, 2009, A1, . Location in patent: Page/Page column 67-68
[3] Patent: WO2008/152394, 2008, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2017/21729, 2017, A1, . Location in patent: Page/Page column 41

[ 288315-03-7 ] Synthesis Path-Downstream 1~6

1
[ 288315-03-7 ]
[ 50712-69-1 ]
5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	Step 1 DIEA (0.196 mL, 1.12 mmol) was added to a stirred mixture of 3,3-difluoroazetidine hydrochloride (64.8 mg, 0.50 mmol) and <strong>[50712-69-1]2-bromomethyl-5-chlorobenzonitrile</strong> (121.0 mg, 0.52 mmol) in CH2Cl2 (7 mL). After 16 h the reaction was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The residue was partitioned between 1N HCl and ether. The aqueous layer was made neutral with NaHCO3 and was extracted with CH2Cl2. The organic layer was dried with Na2SO4 and then evaporated to give 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile (67.8 mg) as a glass: 1H NMR (CDCl3, 400 MHz) delta 3.68 (t, J=11.9 Hz. 4H), 3.93 (s, 2H), 7.54 (m, 2H), 7.63 (d, J=2.2 Hz, 1H).

Reference： [1]Patent: US2002/119992,2002,A1

2
[ 22280-60-0 ]
[ 288315-03-7 ]
[ 1257431-91-6 ]

Yield	Reaction Conditions	Operation in experiment
		psi-Chloro^-methyl-S-nitropyridine (1 g, 5.79 mmol) and 3,3-difluoroazetidine hydrochloride salt (0.948 g, 6.95 mmol) were dissolved in in MeOH (15 ml) followed by addition of TEA (1.22 ml 8.69 mMol) and stirred at 400C for 2h, then at 600C for 17 h. At RT, K2CO3 (0.801 g, 5.79 mmol) was added, followed by 3,3-difluoroazetidine hydrochloridride salt (0.395 g, 2.9 mmol) and the solution was stirred at 60°C for 16h. The reaction mixture was diluted with EtOAc and washed with NaHCO3 aq. sat. soP and brine. The combined organic layers were dried (Na2SO4) and after filtration, the solvent was removed under reduced pressure and the crude product was dried under high vacuum (500C) to obtain the title compound (1.256 g) as a brown solid. The product was used in the next step without further purification. (HPLC: tR 6.468 min (Method B); M+H = 230 MS-ES. )

Reference： [1]Patent: WO2010/139747,2010,A1 .Location in patent: Page/Page column 222

3
[ 288315-03-7 ]
[ 118289-17-1 ]
[ 1459772-15-6 ]

Yield	Reaction Conditions	Operation in experiment
32%		To an ice-cold solution of 2-bromoisonicotinaldehyde (0.40 g, 2.15 mmol) in THF (5 mL) was added 3,3-difluoroazetidine hydrochloride (0.41 g, 3.12 mmol) and N-methyl morpholine (catalytic). The reaction was stirred at 0° C. for 15 min followed by the portion wise addition of sodium cyano borohydride (0.41 g, 6.45 mmol). The mixture was stirred at RT for 16 h. H2O (50 mL) was added followed by extraction with EtOAc (3×100 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by chromatography on silica (30percent EtOAc-Hexane) gave Precursor 49 (0.18 g, 32percent).

Reference： [1]Patent: US2013/252938,2013,A1 .Location in patent: Paragraph 0510

4
[ 288315-03-7 ]
[ 204688-60-8 ]
(R)-tert-butyl 3-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.79%		To a mixture of <strong>[204688-60-8](R)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid</strong> (690 mg, 3.01 mmol) in dichloromethane (40 mL) was sequentially added 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (693.3 mg, 3.63 mmol) and 1- hydroxybenzotriazole (593.43 mg, 4.53 mmol), and then DIPEA (1.55 g, 12.04 mmol) was added drop-wise. The mixture was stirred for 10 mm and 3,3-difluoroazetidine hydrochloride(464.4 g, 3.6 mmol) was added. The reaction was stirred at room temperature overnight. The reaction was diluted with dichloromethane (50 mL x 2) and washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (dichloromethane:methanol = 100: ito 50: ito give (R)-tert-butyl 3-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl)pyrrolidine-i-carboxylate (630 mg, 68.79% yield) as a colorless oil. LC-MS: m/z =249 [M+H-56j.

Reference： [1]Patent: WO2017/27684,2017,A1 .Location in patent: Paragraph 00200

5
[ 288315-03-7 ]
[ 64224-60-8 ]
(5-bromopyrimidin-4-yl)(3,3-difluoroazetidin-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; for 48.0h;	General procedure: To a solution of Intermediate 7 (110 mg, 0.37 mmol), 3-methoxybenzene-1,2- diamine (50 mg, 0.34 mmol) and DIPEA (0.2 mL, 1 mmol) in DMF (2 mL) was added HATU (160 mg, 0.41 mmol). The reaction mixture was stirred at r.t. for 48 h, then partitioned between DCM and water. The organic phase was separated, then dried and concentrated in vacuo. The crude residue was purified by flash column chromatography (0-100% EtOAc/hexanes) to give the title compound (28.7 mg, 20%) as a white solid. LCMS (Method 5): [M+H]+ m/z 415, RT 1.31 minutes.

Reference： [1]Patent: WO2019/138017,2019,A1 .Location in patent: Page/Page column 58; 124

6
[ 288315-03-7 ]
[ 50606-58-1 ]
1-benzyl-3-(3,3-difluoroazetidin-1-yl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 50℃; for 0.5h;	A microwave vial was charged with 1-benzylpiperidin-3-one hydrate HCl salt (100 mg, 0.4 mmol), 3,3-difluoroazetidine hydrochloride (80 mg, 0.6 mmol) and AcOH (47 muL, 0.8 mmol) in THF (1 mL). The resulting suspension was stirred at 50 C until a clear solution was obtained, then NaBH(OAc)3 (261 mg, 1.2 mmol) was added. The reaction mixture was stirred at 50 oC for 30 minutes then allowed to cool to ambient temperature and quenched by the addition of saturated aqueous NaHCO3 solution. The mixture was stirred for 10 minutes then extracted with DCM (x 3). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give 1-benzyl-3-(3,3-difluoroazetidin-1-yl)piperidine, which was used directly in the next step

Reference： [1]Patent: WO2019/148132,2019,A1 .Location in patent: Paragraph 00555; 00556

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Ghs Precautionary Statements

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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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

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[ CAS No. 288315-03-7 ] {[proInfo.proName]}

Quality Control of [ 288315-03-7 ]

Related Doc. of [ 288315-03-7 ]

Product Details of [ 288315-03-7 ]

Calculated chemistry of [ 288315-03-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 288315-03-7 ]

Application In Synthesis of [ 288315-03-7 ]

[ 288315-03-7 ] Synthesis Path-Upstream 1~1

[ 288315-03-7 ] Synthesis Path-Downstream 1~6

Technical Information

Related Functional Groups of [ 288315-03-7 ]

Fluorinated Building Blocks

Related Parent Nucleus of [ 288315-03-7 ]

Aliphatic Heterocycles

Azetidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 288315-03-7 ]

Related Parent Nucleus of
[ 288315-03-7 ]