[ CAS No. 919286-58-1 ] {[proInfo.proName]}

Name: 919286-58-1|(R)-tert-Butyl 2-(bromomethyl)morpholine-4-carboxylate|95%
Brand: Ambeed
SKU: A987917
Rating: 98 (40 reviews)

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3d Animation Molecule Structure of 919286-58-1

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Quality Control of [ 919286-58-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 919286-58-1 ]

SDS Specification

Alternatived Products of [ 919286-58-1 ]

Product Details of [ 919286-58-1 ]

CAS No. :	919286-58-1	MDL No. :	MFCD20489338
Formula :	C₁₀H₁₈BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RLXCSEPIBOWMOJ-QMMMGPOBSA-N
M.W :	280.16	Pubchem ID :	69389434
Synonyms :

Calculated chemistry of [ 919286-58-1 ] Expand+

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 [ 919286-58-1 ]

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 [ 919286-58-1 ]

* 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.

Downstream synthetic route of [ 919286-58-1 ]

[ 919286-58-1 ] Synthesis Path-Downstream 1~18

1
[ 135065-71-3 ]
[ 919286-58-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With polymer supported triphenylphosphine; carbon tetrabromide; In dichloromethane; at 20℃; for 4h;	Step c) 2R-Bromomethyl-morpholine-4-carboxylic acid tert-butyl ester12 g of polymer supported triphenylphosphine was suspended in 100 ml dichloromethane at room temperature, 0.8 g alcohol and 2.4 g CBr4 was added. The mixture was stirred at room temperature for 4 hours, solid supported reagent was removed and residue was concentrated in vacuo. The crude material was dissolved in toluene, treated with 10 g of DARGO G-60, filtered and concentrated in vacuo to yield 0.91 g (88 %) of semi solid 2R- bromomethyl-morpholine-4-carboxylic acid tert-butyl ester.
88%	With carbon tetrabromide; In dichloromethane; at 20℃; for 4h;	12 g of polymer supported triphenylphosphine was suspended in 100 ml dichloromethane at room temperature, 0.8 g alcohol and 2.4 g CBr4 was added. The mixture was stirred at room temperature for 4 hours, solid supported reagent was removed and residue was concentrated in vacuo. The crude material was dissolved in toluene, treated with 10 g of DARGO G-60, filtered and concentrated in vacuo to yield 0.91 g (88 %) of semi solid 2R-bromomethyl-morpholine-4-carboxylic acid tert-butyl ester.
	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at -20 - 20℃;	To a solution of the compound of Example 2(a) (1.80 g, 8.30 mmol) in dichloromethane (100 ml.) at -20 0C was added CBr4 (5.50 g, 16.6 mmol) followed by dropwise addition of a solution of PPh3 (4.60 g, 17.0 mmol) in dichloromethane (80 ml_).After allowing the mixture to warm to RT, the solvent was removed under reduced pressure. Flash chromatography (silica gel, EtOAc/hexanes) gave 2.40 g of the desired compound.

Reference： [1]Patent: WO2007/6715,2007,A1 .Location in patent: Page/Page column 28; 29
[2]Patent: WO2007/6714,2007,A1 .Location in patent: Page/Page column 121
[3]Patent: WO2008/121685,2008,A1 .Location in patent: Page/Page column 40

2
[ 82039-85-8 ]
[ 919286-58-1 ]
[ 919286-59-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	With caesium carbonate; In N,N-dimethyl-formamide; at 40℃; for 16.0h;	Step d) 2R-(2-Ethoxycarbonyl-3-methyl-benzofuran-5-yloxymethyl)- morpholine-4-carboxylic acid tert-butyl esterThe bromide (0.41 g) and 5-hydroxy-3-methylbenzofuran-2-carboxylic acid ethyl ester (0.24 g) was dissolved in 4 ml dry DMF, 1.0 g of CS2CO3 was added, and the mixture was stirred at 40 0C for 16 h. The mixture was diluted with 25 ml EtOAc, washed with water, 1 M citric acid and brine before drying the organic phase over Na2SO4. Concentration in vacuo yielded a brown oily crude product which was purified on neutral alumina to yield 0.14 g (31%) 2R- (2-Ethoxycarbonyl-3-methyl-benzofuran-5-yloxymethyl)-morpholine-4- carboxylic acid tert-butyl ester as a white solid.
31%	With caesium carbonate; In N,N-dimethyl-formamide; at 40℃; for 16.0h;	The bromide (0.41 g) and 5-hydroxy-3-methylbenzofuran-2-carboxylic acid ethyl ester (0.24 g) was dissolved in 4 ml dry DMF, 1.0 g of CS2CO3 was added, and the mixture was stirred at 40 0C for 16 h. The mixture was diluted with 25 ml EtOAc, washed with water, 1 M citric acid and brine before drying the organic phase over Na2SO4.Concentration in vacuo yielded a brown oily crude product which was purified on neutral alumina to yield 0.14 g (31%) 2R-(2-Ethoxycarbonyl-3-methyl-benzofuran-5- yloxymethyl)-morpholine-4-carboxylic acid tert-butyl ester as a white solid.

Reference： [1]Patent: WO2007/6715,2007,A1 .Location in patent: Page/Page column 28; 29
[2]Patent: WO2007/6714,2007,A1 .Location in patent: Page/Page column 121

3
[ 842149-46-6 ]
[ 919286-58-1 ]
[ 937174-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 35℃; for 22.0h;	The compound of intermediate VII (0.80 g, 2.90 mmol), the compound of Example2(b) (0.80 g, 2.90 mmol) and cesium carbonate (2.8Og, 8.50 mmol) in DMF (50 ml.) were stirred at 35 0C for 22 h. The reaction was quenched with sat. NH4CI and extracted with EtOAc. The organic extracts were washed with water, brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue subjected to flash chromatography (silica gel, MeOH/CH2Cl2) to give 0.57 g of the desired compound. MS (ES+) m/z 480 (M+H)+.

Reference： [1]Patent: WO2008/121685,2008,A1 .Location in patent: Page/Page column 40

4
[ 919286-58-1 ]
4-[5-(4-methylphenyl)-1H-pyrrolo[3,2-b]pyridin-6-yl]benzonitrile [ No CAS ]
tert-butyl (2S)-2-[[6-(4-cyanophenyl)-5-(4-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]methyl]morpholine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In N,N-dimethyl-formamide; at 90℃;	[00257j Preparation 1 OA: tert-butyl (2S)-2- [ [6-(4-cyanophenyl)-5 -(4-methylphenyl)pyrrolo [3 ,2-b]pyridin- 1 -yl]methyl]morpholine-4-carboxylate [00258j Tert-butyl (2R)-2-(bromomethyl)morpholine-4-carboxylate (145 mg, 0.52 mmol) was added to a mixture of 4- [5 -(4-methylphenyl)- 1H-pyrrolo [3 ,2-b]pyridin-6- yl]benzonitrile (80 mg, 0.26 mmol) and cesium carbonate (422 mg, 1.30 mmol) in DMF (3 mL). The reaction mixture was stirred at 90 C overnight. The insoluble solids were filtered off and DMF was concentrated in vacuo to give 282 mg (100%) of the title compound as a brown semisolid. This residue was used without purification in the next step. [M+H] Calc’d for C3,H32N403, 509; Found, 509.

Reference： [1]Patent: WO2015/89192,2015,A1 .Location in patent: Paragraph 00257; 00258

5
[ 919286-58-1 ]
4-[5-(4-methylphenyl)-1H-pyrrolo[3,2-b]pyridin-6-yl]benzonitrile [ No CAS ]
tert-butyl (2R)-2-[[6-(4-cyanophenyl)-5-(4-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]methyl]morpholine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 90℃;	[00242] Tert-butyl (2R)-2-(bromomethyl)morpholine-4-carboxylate (145 mg, 0.52 mmol) was added to a mixture of 4-[5-(4-methylphenyl)-lH-pyrrolo[3,2-b]pyridin-6- yljbenzonitrile (80 mg, 0.26 mmol) and cesium carbonate (422 mg, 1.30 mmol) in DMF (3 mL). The reaction mixture was stirred at 90 C overnight. The insoluble solids were filtered off and DMF was concentrated in vacuo to give 282 mg (100%) of the title compound as a brown semisolid. This residue was used without purification in the next step. [M+H] Calc'd for C31H32N4O3, 509; Found, 509.

Reference： [1]Patent: WO2016/37005,2016,A1 .Location in patent: Paragraph 00241-00242

6
[ 919286-58-1 ]
4-bromo-6-hydroxypyrazolo[ 1,5-a]pyridine-3-carbonitrile [ No CAS ]
tert-butyl (R)-2-(((4-bromo-3-cyanopyrazolo[1,5-a]pyridin-6-yl)oxy)methyl)morpholine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In N,N-dimethyl acetamide; at 60℃;	A mixture of (R)-tert-Butyl 2-(bromomethyl)morpholine-4-carboxylate (300 mg, 1.07mmol) and 4-bromo-6-hydroxypyrazolo[ 1,5 -a]pyridine-3 -carbonitrile (Intermediate P1; 255 mg,1.07 mmol) in DMA (2.14 mL) was treated with C52CO3(s) (1.05 g, 3.21 mmol), then stirredovernight at 60 C. After cooling to ambient temperature, the mixture was diluted with DCM, andwashed sequentially with water (3x) and brine (lx). The organic extracts were concentrated invacuo to afford the title compound (468 mg, quantitative yield). ‘H NIVIR (CDC13) 8.12 (s, 1H,),7.43 (d, 1H),7.24 (s, 1H), 7.24, 3.90-4.05 (m, 4H), 3.70-3.89 (m, 2H), 3.42-3.55 (m, 2H), 1.39 (s,12H).

Reference： [1]Patent: WO2018/71447,2018,A1 .Location in patent: Paragraph 001168; 001169; 001170

7
[ 919286-58-1 ]
1,1-dimethylethyl 2-([2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-4-morpholinecarboxylate [ No CAS ]

Reference： [1]Patent: WO2008/121685,2008,A1

8
[ 919286-58-1 ]
4-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(2R)-2-morpholinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol difluoroacetic acid [ No CAS ]

Reference： [1]Patent: WO2008/121685,2008,A1

9
[ 884512-77-0 ]
[ 919286-58-1 ]

Reference： [1]Patent: WO2008/121685,2008,A1

10
[ 919286-58-1 ]
C₁₅H₁₀BrF₂N [ No CAS ]
C₂₅H₂₇BrF₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 25℃; for 14.0h;	To a solution of compound 50 (1.1 g, 3.41 mmol) in DMF (11 mL) was added NaH (273 mg, 6.8 mmol, 60% dispersion) and tert-butyl (R)-2-(bromomethyl)morpholine-4- carboxylate (1.9 g, 6.83 mmol). The mixture was stirred at 25 C for 14 h. The reaction was diluted with water (50 mL), extracted with EA (20 mL x 3). The combined extracts were washed with brine, dried over NaiSCL, filtered and concentrated to get the crude product which was purified by column chromatography to afford compound 51 (1.3 g, 65%). LCMS (ESI, m/z): 523.2 [M+H]+.

Reference： [1]Patent: WO2021/161105,2021,A1 .Location in patent: Paragraph 00297

11
[ 919286-58-1 ]
C₁₆H₁₂F₂N₂O₂ [ No CAS ]
C₂₆H₂₉F₂N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With caesium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 60℃; for 16.0h;	To a solution of compound 58 (110 mg, 364 pmol) in DMF (3.5 mL) was added <strong>[919286-58-1]tert-butyl (R)-2-(bromomethyl)morpholine-4-carboxylate</strong> (204 mg, 728 pmol), CS2CO3 (296 mg, 910 pmol) and Nal (27.3 mg, 182 pmol). Then the mixture was stirred at 60C for 16 h. The mixture was diluted with water (20 mL) and extracted with EA (10 mL x 3). The organic layer was washed with brine (20 mL), dried over NaiSCE, filtered and concentrated. The residue was purified by silica gel chromatography to afford compound 59 (130 mg, 69%). LCMS (ESI, m/z): 502.1 [M+H]+. NMR (400MHz, CDCh) 8.23 (s, 1H), 7.75 (s, 1H), 7.70 (br d, J = 7.7 Hz, 2H), 6.53 (s, 1H), 4.38 - 4.23 (m, 2H), 3.99 (s, 3H), 3.89 - 3.62 (m, 2H), 3.61 - 3.50 (m, 2H), 3.24 (brt, J = 11.5 Hz, 1H), 2.77 - 2.64 (m, 1H), 2.46 (s, 3H), 2.38 - 2.26 (m, 1H), 1.39 (s, 9H).

Reference： [1]Patent: WO2021/161105,2021,A1 .Location in patent: Paragraph 00306

12
[ 919286-58-1 ]
[ 921211-91-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium azide; In N,N-dimethyl-formamide; at 90℃; for 8.0h;	Tert-butyl (R)-2-(bromomethyl)morpholine-4-carboxylate (1.0 g, 3.58 mmol) was dissolved in N,N-dimethylformamide(8 mL), and sodium azide (700 mg, 10.75 mmol) was added. The reaction system was heated to 90 C for 8 h.Then the reaction system was cooled to room temperature, added with water (40 mL) to quench the reaction, andextracted with ethyl acetate (20 mL 3 3). The organic phases were combined, washed with saturated brine (15 mL 32), dried over anhydrous sodium sulfate, and concentrated. The residue was separated by column chromatography togive intermediate 94-2 (738 mg, 92% yield) in the form of a white solid. LC-MS: [M+H]+ = 243.2.

Reference： [1]Patent: EP3889154,2021,A1 .Location in patent: Paragraph 0916-0918

13
[ 919286-58-1 ]
[ 879403-42-6 ]