[ CAS No. 765914-78-1 ] {[proInfo.proName]}

Name: 765914-78-1|4-Boc-2-(bromomethyl)morpholine|97%
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3d Animation Molecule Structure of 765914-78-1

Structure of 765914-78-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 765914-78-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 765914-78-1 ]

SDS Specification

Alternatived Products of [ 765914-78-1 ]

Product Details of [ 765914-78-1 ]

CAS No. :	765914-78-1	MDL No. :	MFCD20489326
Formula :	C₁₀H₁₈BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	280.16	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 765914-78-1 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	65.55
TPSA :	38.77 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) :	-6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.98
Log Po/w (XLOGP3) :	1.56
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	1.3
Log Po/w (SILICOS-IT) :	1.49
Consensus Log Po/w :	1.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.3
Solubility :	1.42 mg/ml ; 0.00506 mol/l
Class :	Soluble
Log S (Ali) :	-1.98
Solubility :	2.91 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.99
Solubility :	2.87 mg/ml ; 0.0103 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.42

Safety of [ 765914-78-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 765914-78-1 ]

* 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 [ 765914-78-1 ]
Downstream synthetic route of [ 765914-78-1 ]

[ 765914-78-1 ] Synthesis Path-Upstream 1~2

1
[ 135065-69-9 ]
[ 765914-78-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With carbon tetrabromide; triphenylphosphine In dichloromethane at -20 - 20℃; for 19.5 h;	To a solution of the compound of Example 2(c) (0.67 g, 3.1 mmol) in dichloromethane (35 mL) at -20 ⁰C was added CBr₄ (2.06 g, 6.17 mmol) followed by dropwise addition of a solution of PPh₃ (1.70 g, 6.48 mmol) in dichloromethane (25 mL). The reaction mixture was held at -15 ⁰C for18 h then stirred at room temperature for 1.5 h. The solvent was removed under reduced pressure and the residue purified by flash chromatography (silica gel, EtOAc/hexanes) gave 0.55 g (63percent) of product that was used in the next step.

Reference： [1] Patent: WO2007/58850, 2007, A2, . Location in patent: Page/Page column 44

2
[ 135065-69-9 ]
[ 765914-78-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With triphenylphosphine In dichloromethane	Step B: 2-Bromomethylmorpholine-4-carboxylic acid tert-butyl ester To a cooled (0° C.) solution of 2-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (1.04 g, 4.79 mmol, see Step 1) in dichloromethane (20 mL) was added CBr₄ (1.98 g, 5.98 mmol). After stirring the mixture for 10 minutes, triphenylphosphine (2.20 g, 8.38 mmol) was added portion-wise. The reaction mixture was stirred at 0° C. for 6 hours and then allowed to warm to room temperature and stirred for 60 hours. The mixture was concentrated under reduced pressure and then diluted with ether. The crude mixture was filtered and the filtrate was concentrated to afford the crude product, which was chromatographed on Biotage eluding with dichloromethane. The desired fractions were combined and concentrated to yield 0.50 g of product (37percent yield).

Reference： [1] Patent: US2004/192653, 2004, A1,

[ 765914-78-1 ] Synthesis Path-Downstream 1~5

1
[ 135065-69-9 ]
[ 765914-78-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at -20 - 20℃; for 19.5h;	To a solution of the compound of Example 2(c) (0.67 g, 3.1 mmol) in dichloromethane (35 mL) at -20 0C was added CBr4 (2.06 g, 6.17 mmol) followed by dropwise addition of a solution of PPh3 (1.70 g, 6.48 mmol) in dichloromethane (25 mL). The reaction mixture was held at -15 0C for18 h then stirred at room temperature for 1.5 h. The solvent was removed under reduced pressure and the residue purified by flash chromatography (silica gel, EtOAc/hexanes) gave 0.55 g (63%) of product that was used in the next step.

Reference： [1]Patent: WO2007/58850,2007,A2 .Location in patent: Page/Page column 44

2
[ 765914-78-1 ]
[ 842149-46-6 ]
1,1-dimethylethyl-2-([2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-4-morpholinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate; In N,N-dimethyl-formamide; at 35℃; for 22h;	The compound of intermediate VII (0.55 g, 1.95 mmol), the compound of Example 2(d) (0.546 g, 1.95 mmol) and cesium carbonate (1.92 g, 5.8 mmol) in DMF (35 ml_) were stirred at 35 0C for 22 h. The product mixture was partitioned between ethyl acetate and water. The organic extracts were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give 0.90 g (96%) of product that was used in the next step.

Reference： [1]Patent: WO2007/58850,2007,A2 .Location in patent: Page/Page column 44-45

3
CBr₄ [ No CAS ]
[ 135065-69-9 ]
[ 765914-78-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With triphenylphosphine; In dichloromethane;	Step B: 2-Bromomethylmorpholine-4-carboxylic acid tert-butyl ester To a cooled (0 C.) solution of 2-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (1.04 g, 4.79 mmol, see Step 1) in dichloromethane (20 mL) was added CBr4 (1.98 g, 5.98 mmol). After stirring the mixture for 10 minutes, triphenylphosphine (2.20 g, 8.38 mmol) was added portion-wise. The reaction mixture was stirred at 0 C. for 6 hours and then allowed to warm to room temperature and stirred for 60 hours. The mixture was concentrated under reduced pressure and then diluted with ether. The crude mixture was filtered and the filtrate was concentrated to afford the crude product, which was chromatographed on Biotage eluding with dichloromethane. The desired fractions were combined and concentrated to yield 0.50 g of product (37% yield).

Reference： [1]Patent: US2004/192653,2004,A1

4
[ 765914-78-1 ]
[ 765914-77-0 ]
[ 765914-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 2,4-dichlorophenoxyacetic acid dimethylamine;	Step C: 5-(2,4-Difluorophenoxy)-1-isobutyl-6-(morpholin-2-ylmethoxy)-1H-indazole To a solution of 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazol-6-ol (0.035 g, 0.11 mmol) in DMA (3.5 mL) was added Cs2CO3 (0.11 g, 0.33 mmol). The mixture stirred at room temperature for 1 hour before the addition of 2-bromomethylmorpholine-4-carboxylic acid tert-butyl ester (0.062 g, 0.22 mmol). The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was diluted with ether and water and the layers were separated. The aqueous layer was extracted with ether (3*) and the combined organic layers were washed with water and brine, and dried over Na2SO4. The crude mixture was concentrated under reduced pressure and purified by reverse phase HPLC to afford the desired product. MS (APCI+) m/z 418 (M+1) detected; 1H NMR (400 mHz, CD3OD) delta 7.90 (s, 1H), 7.38 (s, 1H), 7.21 (s, 1H), 7.11 (m, 1H), 6.84 (m, 2H), 4.22 (m, 2H), 4.18 (d, 2H), 4.05 (m, 2H), 3.31 (m, 3H), 3.03 (m, 2H), 2.31 (m, 1H), 0.92 (d, 6H)

Reference： [1]Patent: US2004/192653,2004,A1

5
[ 765914-78-1 ]
sodium 5-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)amino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-sulfinate [ No CAS ]
N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-((morpholin-2-ylmethyl)sulfonyl)-1H-1,2,4-triazol-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3 mg		Sodium 5-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)amino)-1-((2-(trimethylsilyl)ethoxy)- methyl)-1H-1,2,4-triazole-3-sulfinate (Intermediate B2) (200 mg, 0.438 mmol) was dissolved in DMF (2 mL) and tert-butyl 2-(bromomethyl)morpholine-4-carboxylate (123 mg, 0.438 mmol), Cs2CO3(143 mg, 0.438 mmol) and KI (7.3 mg, 0.044 mmol) were added. The reaction was warmed up to 50 C for 16 h and then to 100 C and stirred for 4 h. The reaction was diluted with 2 M NaOH (aq) (20 mL) and extracted with DCM (2 x 20 mL). The combined organic extracts were dried (phase separator) and concentrated in vacuo. The crude product was dissolved in HCl (4 M in 1,4- dioxane, 2 mL) and stirred for 16 h at RT. The volatiles were evaporated and the product purified by acidic prep HPLC (35-65% MeOH in water) to afford the title compound (3 mg, 2% yield) as a white solid.LCMS m/z 404.4 (M+H)+(ES+).1H NMR (DMSO-d6) d 9.00 (s, 1H), 6.97 (s, 1H), 4.05 - 3.89 (m, 1H), 3.74 - 3.68 (m, 1H), 3.59 (dd, J = 14.8, 4.5 Hz, 1H), 3.54 - 3.43 (m, 3H), 3.04 - 2.98 (m, 1H), 2.83 (m, 5H), 2.76 - 2.69 (m, 1H), 2.64 (m, 5H), 1.98 (p, J = 7.4 Hz, 4H). One exchangeable proton not observed.

Reference： [1]Patent: WO2019/211463,2019,A1 .Location in patent: Page/Page column 369; 370

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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
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P285	In case of inadequate ventilation wear respiratory protection.
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P321
P322
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P342	If experiencing respiratory symptoms:
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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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.
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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.
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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.
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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. 765914-78-1 ] {[proInfo.proName]}

Quality Control of [ 765914-78-1 ]

Related Doc. of [ 765914-78-1 ]

Product Details of [ 765914-78-1 ]

Calculated chemistry of [ 765914-78-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 765914-78-1 ]

Application In Synthesis of [ 765914-78-1 ]

[ 765914-78-1 ] Synthesis Path-Upstream 1~2

[ 765914-78-1 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 765914-78-1 ]

Bromides

Amides

Related Parent Nucleus of [ 765914-78-1 ]

Aliphatic Heterocycles

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 765914-78-1 ]

Related Parent Nucleus of
[ 765914-78-1 ]