[ CAS No. 364793-93-1 ] {[proInfo.proName]}

Name: 364793-93-1|4-((6-Bromopyridin-3-yl)methyl)morpholine|95%
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SKU: A100731
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Quality Control of [ 364793-93-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 364793-93-1 ]

SDS Specification

Alternatived Products of [ 364793-93-1 ]

Product Details of [ 364793-93-1 ]

CAS No. :	364793-93-1	MDL No. :	MFCD11846170
Formula :	C₁₀H₁₃BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QAWNEXYXZJNVGB-UHFFFAOYSA-N
M.W :	257.13	Pubchem ID :	23437896
Synonyms :

Calculated chemistry of [ 364793-93-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.91
TPSA :	25.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.48
Log Po/w (XLOGP3) :	1.06
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	0.99
Log Po/w (SILICOS-IT) :	2.43
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.29
Solubility :	1.33 mg/ml ; 0.00516 mol/l
Class :	Soluble
Log S (Ali) :	-1.18
Solubility :	16.8 mg/ml ; 0.0655 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.47
Solubility :	0.0869 mg/ml ; 0.000338 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.98

Safety of [ 364793-93-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 364793-93-1 ]

* 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 [ 364793-93-1 ]
Downstream synthetic route of [ 364793-93-1 ]

[ 364793-93-1 ] Synthesis Path-Upstream 1~2

1
[ 110-91-8 ]
[ 149806-06-4 ]
[ 364793-93-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 0.666667 h; Stage #2: With sodium hydrogencarbonate In 1,2-dichloro-ethane	To a RB flask containing formylpyridine (9.347 g, 1 equiv.) in 175 mL 1,2-dichloroethane (3.5 mL/mmol) was added morpholine (4.7 mL, 1.07 equiv.) followed by NaBH(OAc)₃(14.819 g, 1.4 equiv.) and acetic acid (3.1 mL, 1.07 equiv.). The flask was loosely capped and the mixture was stirred at r.t. Mixture gets slightly warm. After 40 min, the reaction was quenched with saturated NaHCO₃. When the gas evolution was greatly reduced, 1M NaOH was added to bring the pH to 8-9. The two layers were separated and the aqueous layer was extracted with DCM (.x.3). The organic layer was dried over Na₂SO₄, filtered and solvent was removed in vacuo. The product was filtered through silica with 1000 mL 100:1 EtOAc:NH₄OH to remove baseline material. The material was dissolved in 15 mL EtOAc and 150 mL hexanes was added. The mixture was allowed to sit overnight at 4° C. to crystallize. The supernatant was decanted off and the crystals were washed with a little hexanes which was decanted off. The crystals were transferred to another flask using DCM. LC-MS showed only product. The solvent from the supernatant was removed in vacuo. The remaining mixture was purified by flash column (6.5.x.8.5 cm silica) using 500 mL 8:2 EtOAc; 1400 mL 100:1 EtOAc:NH₄OH. All product fractions were combined giving 10.931 g (85percent) of the 4-((6-bromopyridin-3-yl)methyl)morpholine as a yellow solid.In a RB flask, a mixture of 4-((6-bromopyridin-3-yl)methyl)morpholine (10.959 g, 1 equiv.), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (10.478 g, 1.05 equiv.), 2M potassium phosphate solution (42.5 mL, 2 equiv.) and Pd(PPh₃)₄(2.479, 0.050 equiv.)) in 210 mL dioxane (5 mL/mmol) was sparged with argon for 5 min. The flask was fitted with a septum and argon balloon and the mixture was stirred at 100° C. (amber solution). After 27 h, the mixture was allowed to cool then volume was reduced by at least half in vacuo. The remainder was diluted with water and extracted with EtOAc (.x.3). The organic layers were washed with brine, dried over Na₂SO₄, filtered and solvent was removed in vacuo. The material was purified by column chromatography on silica eluting with DCM:MeOH to give 10.268 g (85percent) of 4-methyl-3-(5-(morpholinomethyl)pyridin-2-yl)aniline as a very viscous dark amber oil.
72%	With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 20℃; for 5 h;	4-[(6-bromopyridin-3-yl)methyl]morpholine In a 50-mL round bottom flask, 6-bromopyridine-3-carbaldehyde (1.200 g, 6.45 mmol, 1.00 equiv) and morpholine (843 mg, 9.68 mmol, 1.50 equiv) were dissolved in 1,2-dichloroethane (15 mL), to which were added NaBH(OAc)₃ (4.102 g, 19.35 mmol, 3.00 equiv) and acetic acid (416 mg, 10.35 mmol 1.07 equiv) at 0° C. The resulting solution was warmed up to room temperature and stirred for 5 h at room temperature. When the reaction was done, it was quenched by the addition of 20 mL sat. sodium bicarbonate solution and the pH value of the resulting mixture was adjusted to 9 using sodium hydroxide solution (1 M). The mixture was then extracted with ethyl acetate (3*30 mL) and the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (5percent to 50percent gradient) to afford 4-[(6-bromopyridin-3-yl)methyl]morpholine (1.2 g, 72percent) as light yellow solid.
57.9%	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 2 h;	To a solution of 6-bromonicotinaldehyde (1.0 g, 5.4 mmol) and morpholine (0.50 g, 5.7 mmol) in 1,2-dichloroethane (30 mL) was added sodium triacetoxyborohydride (1.8 g, 8.5 mmol) and the resulting mixture was stirred at room temperature for 2 h. The mixture was concentrated and purified via ISCO (eluted with MeOH in H₂0 0-100percent) to afford the title compound as a yellow solid (0.80 g, 57.9percent yield). MS (m/z): 256.9/258.9 (M+H)⁺.

57.9%	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 2 h;	To a solution of 6-bromonicotinaldehyde (1.0 g, 5.4 mmol) and morpholine (0.50 g, 5.7 mmol) in 1 ,2-dichloroethane (30 mL) was added sodium triacetoxyborohydride (1.8 g, 8.5 mmol) and the resulting mixture was stirred at room temperature for 2 h. The mixture was concentrated and purified via ISCO (eluted with MeOH in H₂0 0-100percent) to afford the title compound as a yellow solid (0.80 g, 57.9percent yield). MS (m/z): 256.9/258.9 (M+H)⁺.
43%	With sodium cyanoborohydride; acetic acid In ethanol at 20℃; for 3 h;	(181a) 4-[(6-Bromopyridin-3-yl)methyl]morpholine 2-Bromo-5-formylpyridine (0.86 g, 4.6 mmol) was dissolved in ethanol (20 mL), and morpholine (0.48 mL, 5.5 mmol), acetic acid (0.37 mL, 6.4 mmol), and sodium cyanoborohydride (0.43 g, 6.9 mmol) were added thereto. The resulting mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure. To the residue, a saturated sodium carbonate aqueous solution was added. After extraction with methylene chloride, the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen, eluding solvent: ethyl acetate) to obtain 0.51 g (yield: 43percent) of the title compound as a white solid. ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.28 (1H, d, J = 2.3 Hz), 7.54 (1H, dd, J = 2.3, 8.0 Hz), 7.43 (1H, d, J = 8.0 Hz), 3.69 (4H, t, J = 4.7 Hz), 3.45 (2H, s), 2.43 (4H, t, J = 4.7 Hz).

Reference： [1] Patent: US2010/41642, 2010, A1, . Location in patent: Page/Page column 20
[2] Patent: US2016/96834, 2016, A1, . Location in patent: Paragraph 0735
[3] Patent: WO2014/139145, 2014, A1, . Location in patent: Page/Page column 36
[4] Patent: WO2014/139465, 2014, A1, . Location in patent: Page/Page column 37; 38
[5] Patent: EP1798229, 2007, A1, . Location in patent: Page/Page column 162
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247
[7] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5325 - 5329

2
[ 110-91-8 ]
[ 101990-45-8 ]
[ 364793-93-1 ]

Reference： [1] Patent: WO2008/8747, 2008, A1, . Location in patent: Page/Page column 35, 36, 63
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5071 - 5074

[ 364793-93-1 ] Synthesis Path-Downstream 1~13

1
[ 364793-93-1 ]
N₄'-(2,6-dichloro-3,5-dimethoxyphenyl)-[4,5']bipyrimidinyl-6,4'diamine [ No CAS ]
N₄'-(2,6-dichloro-3,5-dimethoxyphenyl)-N₆-(5-morpholin-4-ylmethylpyridin-2-yl)[4,5']bipyrimidinyl-6,4'-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40 - 50%	With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 150℃; for 1.5h;Sealed tube;	A suspension of aminopyrimidopyrimidine 10 (2.50 g, 6.36 mmol), 4-(6-bromo- pyridin-3-ylmethyl)-morpholine 13 (2.45g, 9.54mmol), Xantphos (736 mg, 1.27 mmol), palladium (II) acetate (142 mg, 0.64 mmol) and cesium carbonate (4.14, 12.72 mmol) in dioxane (30 niL) is degassed, sealed in a pressure tube. After stirring at 150 0C for 1.5 hours, the reaction is cooled and quenched with diethyldithiocarbamic acid sodium salt solution (30 mL) and water (30 mL). A brown solid is collected by filtration, washed with water and dried. The crude product triturated by stirring/filtering successively in ether (300 mL) and CH2Cl2. A light brown solid is collected and the brown color is removed by flash chromatographic purification (SiO2, 1%NH3 in CH3OH/EtOAc from 0 to 10%) to give a white powder: 1H NMR 400 MHz (DMSO-d6) δ 11.30 (s, IH), 10.47 (s, IH), 8.87 (s, 2H), 8.53 (s, IH), 8.43 (s, IH), 8.30 (s, IH), 7.72 (s, 2H), 6.95 (s, IH), 3.97 (s, 6H), 3.59 (m, 4H), 3.46 (s, 2H), 2.37 (s, 4H); MS m/z 569.1 (M+ 1).

Reference： [1]Patent: WO2008/8747,2008,A1 .Location in patent: Page/Page column 30, 35

2
[ 110-91-8 ]
[ 101990-45-8 ]
[ 364793-93-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 1.0h;	The crude is dissolved in anhydrous THF (40 mL). DIEA (5.03 mL, 29mmol) is added, followed by addition of morpholine (3.0 mL, 34.3 mmol). After stirring at room temperature for 1 hour, the reaction is partitioned between saturated NaHCO3 (30 mL) and EtOAc (100 mL) and separated. EtOAc is washed with brine (30 mL), dried and evaporated. The crude is purified by flash column chromatography (SiO2, 1%NH3 in CH3OH/CH2C12 from 0 to 10%) to give a light tan colored solid: 1H NMR 400 MHz (DMSO-d6) δ 8.31 (d, J = 2.4 Hz, IH), 7.69 (dd, J = 2.4, 8.4 Hz, IH), 7.62 (d, J = 8.0 Hz, IH), 3.57 (t, J = 4.8 Hz, 4H), 3.48 (s, 2H), 2.35 (t, J = 4.4 Hz, 4H); MS m/z 257.1 (M+l).

Reference： [1]Patent: WO2008/8747,2008,A1 .Location in patent: Page/Page column 35, 36, 63
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5071 - 5074

3
[ 364793-93-1 ]
[ 2298-07-9 ]
[ 945537-30-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4242 - 4247

4
[ 110-91-8 ]
[ 149806-06-4 ]
[ 364793-93-1 ]

Yield	Reaction Conditions	Operation in experiment
85%		To a RB flask containing formylpyridine (9.347 g, 1 equiv.) in 175 mL 1,2-dichloroethane (3.5 mL/mmol) was added morpholine (4.7 mL, 1.07 equiv.) followed by NaBH(OAc)3 (14.819 g, 1.4 equiv.) and acetic acid (3.1 mL, 1.07 equiv.). The flask was loosely capped and the mixture was stirred at r.t. Mixture gets slightly warm. After 40 min, the reaction was quenched with saturated NaHCO3. When the gas evolution was greatly reduced, 1M NaOH was added to bring the pH to 8-9. The two layers were separated and the aqueous layer was extracted with DCM (×3). The organic layer was dried over Na2SO4, filtered and solvent was removed in vacuo. The product was filtered through silica with 1000 mL 100:1 EtOAc:NH4OH to remove baseline material. The material was dissolved in 15 mL EtOAc and 150 mL hexanes was added. The mixture was allowed to sit overnight at 4 C. to crystallize. The supernatant was decanted off and the crystals were washed with a little hexanes which was decanted off. The crystals were transferred to another flask using DCM. LC-MS showed only product. The solvent from the supernatant was removed in vacuo. The remaining mixture was purified by flash column (6.5×8.5 cm silica) using 500 mL 8:2 EtOAc; 1400 mL 100:1 EtOAc:NH4OH. All product fractions were combined giving 10.931 g (85%) of the 4-((6-bromopyridin-3-yl)methyl)morpholine as a yellow solid.In a RB flask, a mixture of 4-((6-bromopyridin-3-yl)methyl)morpholine (10.959 g, 1 equiv.), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (10.478 g, 1.05 equiv.), 2M potassium phosphate solution (42.5 mL, 2 equiv.) and Pd(PPh3)4 (2.479, 0.050 equiv.)) in 210 mL dioxane (5 mL/mmol) was sparged with argon for 5 min. The flask was fitted with a septum and argon balloon and the mixture was stirred at 100 C. (amber solution). After 27 h, the mixture was allowed to cool then volume was reduced by at least half in vacuo. The remainder was diluted with water and extracted with EtOAc (×3). The organic layers were washed with brine, dried over Na2SO4, filtered and solvent was removed in vacuo. The material was purified by column chromatography on silica eluting with DCM:MeOH to give 10.268 g (85%) of 4-methyl-3-(5-(morpholinomethyl)pyridin-2-yl)aniline as a very viscous dark amber oil.
72%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 0 - 20℃; for 5.0h;	4-[(6-bromopyridin-3-yl)methyl]morpholine In a 50-mL round bottom flask, 6-bromopyridine-3-carbaldehyde (1.200 g, 6.45 mmol, 1.00 equiv) and morpholine (843 mg, 9.68 mmol, 1.50 equiv) were dissolved in 1,2-dichloroethane (15 mL), to which were added NaBH(OAc)3 (4.102 g, 19.35 mmol, 3.00 equiv) and acetic acid (416 mg, 10.35 mmol 1.07 equiv) at 0 C. The resulting solution was warmed up to room temperature and stirred for 5 h at room temperature. When the reaction was done, it was quenched by the addition of 20 mL sat. sodium bicarbonate solution and the pH value of the resulting mixture was adjusted to 9 using sodium hydroxide solution (1 M). The mixture was then extracted with ethyl acetate (3*30 mL) and the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (5% to 50% gradient) to afford 4-[(6-bromopyridin-3-yl)methyl]morpholine (1.2 g, 72%) as light yellow solid.
57.9%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 2.0h;	To a solution of 6-bromonicotinaldehyde (1.0 g, 5.4 mmol) and morpholine (0.50 g, 5.7 mmol) in 1,2-dichloroethane (30 mL) was added sodium triacetoxyborohydride (1.8 g, 8.5 mmol) and the resulting mixture was stirred at room temperature for 2 h. The mixture was concentrated and purified via ISCO (eluted with MeOH in H20 0-100%) to afford the title compound as a yellow solid (0.80 g, 57.9% yield). MS (m/z): 256.9/258.9 (M+H)+.

57.9%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 2.0h;	To a solution of 6-bromonicotinaldehyde (1.0 g, 5.4 mmol) and morpholine (0.50 g, 5.7 mmol) in 1 ,2-dichloroethane (30 mL) was added sodium triacetoxyborohydride (1.8 g, 8.5 mmol) and the resulting mixture was stirred at room temperature for 2 h. The mixture was concentrated and purified via ISCO (eluted with MeOH in H20 0-100%) to afford the title compound as a yellow solid (0.80 g, 57.9% yield). MS (m/z): 256.9/258.9 (M+H)+.
43%	With sodium cyanoborohydride; acetic acid; In ethanol; at 20℃; for 3.0h;	(181a) 4-[(6-Bromopyridin-3-yl)methyl]morpholine 2-Bromo-5-formylpyridine (0.86 g, 4.6 mmol) was dissolved in ethanol (20 mL), and morpholine (0.48 mL, 5.5 mmol), acetic acid (0.37 mL, 6.4 mmol), and sodium cyanoborohydride (0.43 g, 6.9 mmol) were added thereto. The resulting mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure. To the residue, a saturated sodium carbonate aqueous solution was added. After extraction with methylene chloride, the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen, eluding solvent: ethyl acetate) to obtain 0.51 g (yield: 43%) of the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm: 8.28 (1H, d, J = 2.3 Hz), 7.54 (1H, dd, J = 2.3, 8.0 Hz), 7.43 (1H, d, J = 8.0 Hz), 3.69 (4H, t, J = 4.7 Hz), 3.45 (2H, s), 2.43 (4H, t, J = 4.7 Hz).

Reference： [1]Patent: US2010/41642,2010,A1 .Location in patent: Page/Page column 20
[2]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0735
[3]Patent: WO2014/139145,2014,A1 .Location in patent: Page/Page column 36
[4]Patent: WO2014/139465,2014,A1 .Location in patent: Page/Page column 37; 38
[5]Patent: EP1798229,2007,A1 .Location in patent: Page/Page column 162
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4242 - 4247
[7]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5325 - 5329

5
[ 364793-93-1 ]
[ 892408-41-2 ]
2-methyl-4-[4-(methylsulfanyl)phenyl]-7-[5-(morpholin-4-ylmethyl)pyridin-2-yloxy]-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5325 - 5329

6
[ 364793-93-1 ]
1-[5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl]-3-[4-(5-(morpholin-4-yl-methyl)pyridin-2-yl)-naphthalen-1-yl]-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4242 - 4247

7
[ 882670-69-1 ]
[ 364793-93-1 ]
[ 1207877-81-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃;Inert atmosphere;	To a RB flask containing formylpyridine (9.347 g, 1 equiv.) in 175 mL 1,2-dichloroethane (3.5 mL/mmol) was added morpholine (4.7 mL, 1.07 equiv.) followed by NaBH(OAc)3 (14.819 g, 1.4 equiv.) and acetic acid (3.1 mL, 1.07 equiv.). The flask was loosely capped and the mixture was stirred at r.t. Mixture gets slightly warm. After 40 min, the reaction was quenched with saturated NaHCO3. When the gas evolution was greatly reduced, 1M NaOH was added to bring the pH to 8-9. The two layers were separated and the aqueous layer was extracted with DCM (×3). The organic layer was dried over Na2SO4, filtered and solvent was removed in vacuo. The product was filtered through silica with 1000 mL 100:1 EtOAc:NH4OH to remove baseline material. The material was dissolved in 15 mL EtOAc and 150 mL hexanes was added. The mixture was allowed to sit overnight at 4 C. to crystallize. The supernatant was decanted off and the crystals were washed with a little hexanes which was decanted off. The crystals were transferred to another flask using DCM. LC-MS showed only product. The solvent from the supernatant was removed in vacuo. The remaining mixture was purified by flash column (6.5×8.5 cm silica) using 500 mL 8:2 EtOAc; 1400 mL 100:1 EtOAc:NH4OH. All product fractions were combined giving 10.931 g (85%) of the 4-((6-bromopyridin-3-yl)methyl)morpholine as a yellow solid.In a RB flask, a mixture of 4-((6-bromopyridin-3-yl)methyl)morpholine (10.959 g, 1 equiv.), <strong>[882670-69-1]4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (10.478 g, 1.05 equiv.), 2M potassium phosphate solution (42.5 mL, 2 equiv.) and Pd(PPh3)4 (2.479, 0.050 equiv.)) in 210 mL dioxane (5 mL/mmol) was sparged with argon for 5 min. The flask was fitted with a septum and argon balloon and the mixture was stirred at 100 C. (amber solution). After 27 h, the mixture was allowed to cool then volume was reduced by at least half in vacuo. The remainder was diluted with water and extracted with EtOAc (×3). The organic layers were washed with brine, dried over Na2SO4, filtered and solvent was removed in vacuo. The material was purified by column chromatography on silica eluting with DCM:MeOH to give 10.268 g (85%) of 4-methyl-3-(5-(morpholinomethyl)pyridin-2-yl)aniline as a very viscous dark amber oil.

Reference： [1]Patent: US2010/41642,2010,A1 .Location in patent: Page/Page column 20

8
[ 364793-93-1 ]
methyl 3-(2-(2-aminopyrimidin-5-yl)ethyl)-4-fluoro-5-methoxybenzoate [ No CAS ]
methyl 4-fluoro-3-methoxy-5-(2-(2-((5-(morpholinomethyl)pyridin-2-yl)amino) pyrimidin-5-yl)ethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.3%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 130℃; for 0.25h;Microwave irradiation;	A mixture of methyl 3-(2-(2-aminopyrimidin-5-yl)ethyl)-4-fluoro-5-methoxybenzoate (0.09 g, 0.30 mmol), 4-((6-bromopyridin-3-yl)methyl)morpholine (0.12 g, 0.47 mmol), Cs2C03 (0.20 g, 0.62 mmol), palladium( II )acetate (0.02 g, 0.089 mmol) and Xantphos (0.02 g, 0.035 mmol) in dioxane (6 mL) was heated at 130C under microwave for 15 min. Then the mixture was concentrated and the residue was purified via ISCO (eluted with MeOH in H20 0-100%) to afford the title compound as a yellow solid (0.06 g, 42.3% yield). MS (m/z): 482.3 (M+H)+.
42.3%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 130℃; for 0.25h;Microwave irradiation;	A mixture of methyl 3-(2-(2-aminopyrimidin-5-yl)ethyl)-4-fluoro-5-methoxybenzoate (0.09 g, 0.30 mmol), 4-((6-bromopyridin-3-yl)methyl)morpholine (0.12 g, 0.47 mmol), CS2CO3 (0.20 g, 0.62 mmol), palladium( II )acetate (0.02 g, 0.089 mmol) and Xantphos (0.02 g, 0.035 mmol) in dioxane (6 mL) was heated at 130C under microwave for 15 min. Then the mixture was concentrated and the residue was purified via ISCO (eluted with MeOH in H20 0-100%) to afford the title compound as a yellow solid (0.06 g, 42.3% yield). MS (m/z): 482.3 (M+H)+.

Reference： [1]Patent: WO2014/139145,2014,A1 .Location in patent: Page/Page column 78; 79
[2]Patent: WO2014/139465,2014,A1 .Location in patent: Page/Page column 85; 86

9
[ 364793-93-1 ]
4-fluoro-3-methoxy-5-(2-(2-((5-(morpholinomethyl)pyridin-2-yl)amino)pyrimid in-5-yl)ethyl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2014/139145,2014,A1

10
[ 364793-93-1 ]
4-fluoro-3-methoxy-N-methyl-5-(2-(2-((5-(morpholinomethyl)pyridin-2-yl)amino)pyrimidin-5-yl)ethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2014/139145,2014,A1
[2]Patent: WO2014/139465,2014,A1

11
[ 364793-93-1 ]
5-(morpholin-4-ylmethyl)pyridine-2-carbaldehyde [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

12
[ 364793-93-1 ]
tert-butyl N-[(2-fluoro-4-[2-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-imidazo[4,5-b]pyridin-7-yl]phenyl)methyl]carbamate [ No CAS ]

Reference： [1]Patent: US2016/96834,2016,A1

13
[ 364793-93-1 ]
[ 7486-35-3 ]
4-[(6-ethenylpyridin-3-yl)methyl]morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In toluene; at 110℃;Inert atmosphere;	4-[(6-ethenylpyridin-3-yl)methyl]morpholine In a 50-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, <strong>[364793-93-1]4-[(6-bromopyridin-3-yl)methyl]morpholine</strong> (256 mg, 1.00 mmol, 1.00 equiv), tributyl(ethenyl)stannane (748 mg, 2.24 mmol, 1.52 equiv) and Pd(PPh3)4(181 mg, 0.14 mmol, 0.10 equiv, 90%) were mixed in toluene (6 mL) at room temperature. The resulting mixture was then stirred overnight at 110 C. After the reaction was done, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (3*150 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with methanol in dichloromethane (1% to 10% gradient) to afford 4-[(6-ethenylpyridin-3-yl)methyl]morpholine (310 mg, crude) as yellow oil. MS: m/z=205.0 [M+H]+.

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0736

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Related Functional Groups of
[ 364793-93-1 ]

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[ 364793-93-1 ]

Morpholines

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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. 364793-93-1 ] {[proInfo.proName]}

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Physicochemical Properties

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Lipophilicity

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Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 364793-93-1 ]

[ 364793-93-1 ] Synthesis Path-Upstream 1~2

[ 364793-93-1 ] Synthesis Path-Downstream 1~13

Related Functional Groups of [ 364793-93-1 ]

Bromides

Related Parent Nucleus of [ 364793-93-1 ]

Morpholines

Pyridines

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Response

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Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 364793-93-1 ]

Related Parent Nucleus of
[ 364793-93-1 ]