[ CAS No. 200064-13-7 ]

Name: 200064-13-7|3-Bromo-5-morpholinopyridine|98%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 200064-13-7 ]

CAS No. :	200064-13-7	MDL No. :	MFCD11656285
Formula :	C₉H₁₁BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	243.10 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 200064-13-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.44
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.66
TPSA :	25.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.26
Log Po/w (XLOGP3) :	1.29
Log Po/w (WLOGP) :	1.3
Log Po/w (MLOGP) :	0.97
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	1.59

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.44
Solubility :	0.892 mg/ml ; 0.00367 mol/l
Class :	Soluble
Log S (Ali) :	-1.42
Solubility :	9.19 mg/ml ; 0.0378 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.07
Solubility :	0.207 mg/ml ; 0.000853 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.15

Safety of [ 200064-13-7 ]

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 [ 200064-13-7 ]

* 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.

Downstream synthetic route of [ 200064-13-7 ]

[ 200064-13-7 ] Synthesis Path-Downstream 1~20

1
[ 110-91-8 ]
[ 625-92-3 ]
[ 200064-13-7 ]
4-(3-Bromo-pyridin-4-yl)-morpholine [ No CAS ]
3,5-di-(4-morpholyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 22% 2: 17% 3: 40%	With sodium amide; sodium t-butanolate In tetrahydrofuran at 40 - 50℃; for 0.75h;

Reference： [1]Vinter-Pasquier, Karine; Jamart-Gregoire, Brigitte; Caubere, Paul [Heterocycles, 1997, vol. 45, # 11, p. 2113 - 2129]

2
[ 110-91-8 ]
[ 200064-13-7 ]
3,5-di-(4-morpholyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium amide; <i>tert</i>-butyl alcohol In tetrahydrofuran at 20℃; for 0.75h;

Reference： [1]Vinter-Pasquier, Karine; Jamart-Gregoire, Brigitte; Caubere, Paul [Heterocycles, 1997, vol. 45, # 11, p. 2113 - 2129]

3
[ 200064-13-7 ]
[ 1066-54-2 ]
[ 926009-41-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With piperidine; copper(l) iodide at 100℃; for 48h;

Reference： [1]Matulenko, Mark A.; Paight, Ernest S.; Frey, Robin R.; Gomtsyan, Arthur; DiDomenico Jr., Stanley; Jiang, Meiqun; Lee, Chih-Hung; Stewart, Andrew O.; Yu, Haixia; Kohlhaas, Kathy L.; Alexander, Karen M.; McGaraughty, Steve; Mikusa, Joseph; Marsh, Kennan C.; Muchmore, Steven W.; Jakob, Clarissa L.; Kowaluk, Elizabeth A.; Jarvis, Michael F.; Bhagwat, Shripad S. [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605]

4
[ 110-91-8 ]
[ 625-92-3 ]
[ 200064-13-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 115℃; for 18h; Inert atmosphere;
65%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 4h; Inert atmosphere; Microwave irradiation;	1 To a solution of 3,5-dibromopyridine (XL) (1.68 g, 7.1 mmol) in dioxane (14 mL) was added morpholine (682 mg, 7.8 mmol), CsCO3 (3.24 g, 9.93 mmol) and xantphos (123 mg, 0.21 mmol). The solution was degassed before adding Pd2(dba)3 (195 mg, 0.21 mmol). The reaction was microwaved at 90° C. for 4 h. The reaction was poured into a mixture of CHCl3/ H2O; the aqueous layer was separated, washed with water, then brine and concentrated under vacuum. The crude product was purified on a silica gel column (100% hexane→1:3 EtOAc:hexane) to give 4-(5-bromopyridin-3-yl)morpholine (XLI) as a yellow solid (1.12 g, 4.6 mmol, 65% yield). ESIMS found C9H11BrN2O m/z 244 (M+H).
63%	In 1-methyl-pyrrolidin-2-one; toluene at 180℃; for 1.1h; Microwave irradiation;

55%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 12h; Heating;
38%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 5h; Inert atmosphere;	96.1 Step 7: Preparation of 4-(5-bromopyridin-3-yl)morpholine To a solution of 3,5-dibromopyridine (1.10 g, 4.60 mmol) in dioxane (2 mL) was added morpholine (200 mg, 2.30 mmol), CS2CO3 (1.10 g, 3.20 mmol), XantPhos (39 mg, 0.068 mmol) and Pd2(dba)3 (62 mg, 0.068 mmol). The resulting mixture was degassed and purged with N2 for three times and then stirred at 90 °C for 5 h under N2. A yellow suspension was formed. TLC-Plate 1 (EtO Ac/PE = 1 : 1) showed starting material was consumed and new spots were formed at Rf = 0.22 and 0.82. LCMS showed the starting material was consumed nearly and the purity of the desired product (Rt = 0.439 min; MS Calcd: 242.0; MS Found: 244.7 [M+H]+). H2O (15 mL) and DCM (20 mL) was added to the reaction mixture and then separated. The combined organic layer was washed with brine (10 mL) dried over anhydrous Na2S04 and concentrated. The crude product was purified by combi flash (50% EtOAc in pentane) and concentrated to give 4-(5-bromopyridin-3-yl)morpholine (300 mg, yield: 38%) as a light yellow solid. (1285) NMR (400 MHz, CDCh) d 3.21 (4H, t, J= 5.2 Hz), 3.87 (4H, t, J= 4.8 Hz), 7.30 (1H, t, J = 2.0 Hz), 8.16 (1H, d, .7= 2.0 Hz), 8.21 (1H, d, .7= 2.4 Hz).
33%	With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 4.5h; Electrochemical reaction;
19.5%	In 1-methyl-pyrrolidin-2-one; toluene at 180℃; for 1h; Microwave irradiation;	1 Step 1: 4-(5-bromopyridin-3-yl)morpholine To a solution of morpholine (3.67 g, 4.23 mmol), NMP (2 mL) and toluene (4 mL) was added 3,5-dibromopyridine (1.00 g, 4.20 mmol) and the mixture was heated under microwave conditions at 180 °C for 1 h. The solution was partitioned between DCM and water, the organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography eluting with (EtOAc: PE= 1:5). (200 mg, yield 19.5%) MS (ESI+) e/z: 243.0 [M+1]+LCMS.
	With sodium t-butanolate In toluene at 120℃; for 5h;	80 A mixture of 3,5-dibromopyridine (2.121 g, 8.95 mmol), BINAP (0.279 g, 0.448 mmol), Pd2(dba)3 (0.137 g, 0.149 mmol) and sodium fert-butoxide (1.434 g, 14.92 mmol) in toluene (50 mL) was added morpholine (0.65 mL, 7.46 mmol). The mixture was then heated at 120 °C for ca. 5 h. After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-50% ethyl acetate in DCM, to give the title compound (1 .62 g). LCMS (A) m/z: 243/245 [M+1]+, Rt 0.83 min (acidic),
1.42 g	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; Sealed tube; Inert atmosphere;	57 Synthesis of 6-(5-morpholino-3-pyridyl)-3,4-dihydro-2H-1,8-naphthyridine-1-carboxamide (Compound 90, Table 1) In a sealable tube, to a mixture of 3,5-dibromo-pyridine (3.3 g, 13.8 mmol) and NaOtBu (0.051 g, 23 mmol) in toluene (70 mL), is added morpholine (1.0 g, 11.5 mmol). The mixture is bubbled with Argon for 5 min, and then BINAP (428.9 mg, 0.69 mmol) and Pd2(dba)3 (210.2 mg, 0.23 mmol) are added. The reaction mixture is bubbled with Argon for another 5 min. Then the cap is sealed and the reaction mixture is heated at 120° C. overnight and then is cooled to room temperature. The reaction mixture is filtered through diatomaceous earth and washed with DCM. The filtrate is partitioned between water and DCM. The aqueous phase is further extracted with DCM (2×). The combined DCM phases are concentrated. The crude is purified by flash chromatography on a silica gel column (EtOAc/ heptane 0 to 50% gradient, then 50%) to provide 1.42 g of 4-(5-bromo-3-pyridyl)morpholine.

Reference： [1]Location in patent: experimental part Bunnelle, William H.; Tietje, Karin R.; Frost, Jennifer M.; Peters, Dan; Ji, Anguo; Li, Tao; Scanio, Marc J. C.; Shi, Lei; Anderson, David J.; Dyhring, Tino; Grønlien, Jens H.; Ween, Hilde; Thorin-Hagene, Kirsten; Meyer, Michael D. [Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4126 - 4141]
[2]Current Patent Assignee: BIOSPLICE THERAPEUTICS INC - US2013/267495, 2013, A1 Location in patent: Paragraph 0438-0439
[3]Location in patent: experimental part Dandu, Reddeppa Reddy; Rose, Adam C.; Hudkins, Robert L. [Heterocycles, 2011, vol. 83, # 4, p. 875 - 881]
[4]Matulenko, Mark A.; Paight, Ernest S.; Frey, Robin R.; Gomtsyan, Arthur; DiDomenico Jr., Stanley; Jiang, Meiqun; Lee, Chih-Hung; Stewart, Andrew O.; Yu, Haixia; Kohlhaas, Kathy L.; Alexander, Karen M.; McGaraughty, Steve; Mikusa, Joseph; Marsh, Kennan C.; Muchmore, Steven W.; Jakob, Clarissa L.; Kowaluk, Elizabeth A.; Jarvis, Michael F.; Bhagwat, Shripad S. [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605]
[5]Current Patent Assignee: HIBERCELL INC - WO2019/126730, 2019, A1 Location in patent: Paragraph 0460
[6]Daili, Farah; Sengmany, Stéphane; Léonel, Eric [European Journal of Organic Chemistry, 2021, vol. 2021, # 17, p. 2462 - 2469]
[7]Current Patent Assignee: EPIZYME, INC. - WO2014/100716, 2014, A1 Location in patent: Paragraph 00230
[8]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/75559, 2011, A1 Location in patent: Page/Page column 61; 62
[9]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2014/323468, 2014, A1 Location in patent: Paragraph 0542

5
[ 200064-13-7 ]
[ 926009-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 89 percent / piperidine; CuI / Pd(PPh₃)2Cl₂ / 48 h / 100 °C 2: K₂CO₃ / methanol

6
[ 200064-13-7 ]
C₂₁H₁₈N₅ClO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 89 percent / piperidine; CuI / Pd(PPh₃)2Cl₂ / 48 h / 100 °C 2: K₂CO₃ / methanol 3: 16 percent / Et₃N; CuI / Pd(PPh₃)2Cl₂ / acetonitrile / 1 h / 50 °C

7
[ 37828-58-3 ]
[ 625-92-3 ]
[ 200064-13-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at 0 - 25℃; for 1.16667h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: lithium morpholide Further stages;

Reference： [1]Kienle, Marcel; Dunst, Cora; Knochel, Paul [Organic Letters, 2009, vol. 11, # 22, p. 5158 - 5161]

8
[ 200064-13-7 ]
[ 250275-15-1 ]
[ 1173179-64-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4126 - 4141

Yield	Reaction Conditions	Operation in experiment
64.9%	With potassium carbonate In N,N-dimethyl-formamide at 120℃;	General procedure: To a solution of 3,5-dibromopyridine (XXXVIII) (2.90 g, 12.24 mmol) in dry DMF (20 mL) was added 1 -methylpiperazine (2.987 mL, 26.93 mmol) and K2C03 (5.58 g, 40.39 mmol). The reaction was heated at 120°C overnight. An additional portion of 1- methylpiperazine (6 mL) was added and heating was continued for another 24 h. The reaction was poured into ice water and filtered. The filtrate was extracted with 66% MeOH/CHCl3. The organic layer was dried over MgS04, filtered and concentrated under vacuum to yield l -(5- bromopyridin-3-yl)-4-methylpiperazine (XL) as a brown viscous oil (2.49 g, 9.76 mmol, 79.8% yield). ESIMS found for Ci0Hi4BrN3 mlz 256 (M+H).
40%
40%

10
[ 1413439-81-2 ]
[ 200064-13-7 ]
4-(3-Bromo-pyridin-4-yl)-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: diethylamine; n-hexylmagnesium chloride / tetrahydrofuran / -78 °C 1.2: -40 - 0 °C 2.1: cesium fluoride

Reference： [1]Goetz, Adam E.; Garg, Neil K. [Nature Chemistry, 2013, vol. 5, # 1, p. 54 - 60]

11
[ 110-91-8 ]
[ 1413439-82-3 ]
[ 200064-13-7 ]
4-(3-Bromo-pyridin-4-yl)-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride Overall yield = 64 %; regioselective reaction;

Reference： [1]Goetz, Adam E.; Garg, Neil K. [Nature Chemistry, 2013, vol. 5, # 1, p. 54 - 60]

12
[ 109-00-2 ]
[ 200064-13-7 ]
4-(3-Bromo-pyridin-4-yl)-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane 2.1: N,N,N,N,-tetramethylethylenediamine; t-butyldimethylsiyl triflate / tetrahydrofuran; diethyl ether / -78 - 23 °C 2.2: -78 °C 2.3: -78 °C 3.1: diethylamine; n-hexylmagnesium chloride / tetrahydrofuran / -78 °C 3.2: -40 - 0 °C 4.1: cesium fluoride

Reference： [1]Goetz, Adam E.; Garg, Neil K. [Nature Chemistry, 2013, vol. 5, # 1, p. 54 - 60]

13
[ 1413439-93-6 ]
[ 200064-13-7 ]
4-(3-Bromo-pyridin-4-yl)-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N,N,N,N,-tetramethylethylenediamine; t-butyldimethylsiyl triflate / tetrahydrofuran; diethyl ether / -78 - 23 °C 1.2: -78 °C 1.3: -78 °C 2.1: diethylamine; n-hexylmagnesium chloride / tetrahydrofuran / -78 °C 2.2: -40 - 0 °C 3.1: cesium fluoride

Reference： [1]Goetz, Adam E.; Garg, Neil K. [Nature Chemistry, 2013, vol. 5, # 1, p. 54 - 60]

14
[ 73183-34-3 ]
[ 200064-13-7 ]
[ 1201644-33-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate In 1,4-dioxane at 100℃; for 5h;	81 A mixture of 4-(5-bromo-3-pyridinyl)morpholine (Description 80) (360 mg, 1.481 mmol), bis(pinacolato)diboron (564 mg, 2.221 mmol), PdCI2(dppf).DCM adduct (121 mg, 0.148 mmol) and potassium acetate (436 mg, 4.44 mmol) in 1 ,4-dioxane (6 mL) was heated at 100 °C for ca. 5 h. The mixture was concentrated and then diluted with DCM (50 mL) and washed with water (30 mL x 3). The organic layer was dried and concentrated, to give what was thought to be the title compound (430 mg) which was used in the next step (Suzuki coupling) without further purification. LCMS (A) m/z: 209 [M+1 ]+, Rt 0.42 min (acidic) [corresponding to the boronic acid].

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/75559, 2011, A1 Location in patent: Page/Page column 62

15
[ 200064-13-7 ]
[ 1312593-87-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 5 h / 100 °C 2: potassium carbonate; water / tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; 1,4-dioxane / 0.25 h / 120 °C / microwave irradiation

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/75559, 2011, A1

16
[ 1616064-76-6 ]
[ 200064-13-7 ]
[ 1616064-49-3 ]

Yield	Reaction Conditions	Operation in experiment
3.3%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; XPhos In 1,4-dioxane at 120℃; for 1h; Microwave irradiation;	2 Step 2: l-(3-(3,4-dihydroisoquinolin-2(lH)-yl)-2-hydroxypropyl)-4-(5- morpholinopyridin-3-yl)piperazin-2-one A solution of 4-(5-bromopyridin-3-yl)morpholine (100 mg, 0.413 mmol), l-(3- (3,4-dihydroisoquinolin-2(lH)-yl)-2-hydroxypropyl)piperazin-2-one (119 mg, 0.413 mmol), X-phos (20 mg, 0.042 mmol), Pd(dba)2 (10 mg, 0.017 mmol) and NaOiBu (59.0 mg, 0.615 mmol) in dioxane (5 mL) was heated at 120 °C 1 h under microwave conditions. The crude reaction mixture was filtered, concentrated, and purified by preprative HPLC purification. (6.10 mg, yield 3.3%) 1H NMR (MeOD, 400 MHz), δ ppm: 7.76 (d, J=2.3 Hz, 1H), 7.72 (d, J=2.0 Hz, 1H), 7.17 - 7.07 (m, 3H), 7.07 - 7.01 (m, 1H), 6.89 - 6.80 (m, 1H), 4.28 - 4.18 (m, 1H), 3.93 (s, 2H), 3.89 - 3.82 (m, 4H), 3.82 - 3.72 (m, 4H), 3.71 - 3.63 (m, 1H), 3.59 (t, J=1.0 Hz, 2H), 3.32 - 3.28 (m, 1H), 3.27 - 3.16 (m, 4H), 2.99 - 2.90 (m, 2H), 2.90 - 2.81 (m, 2H), 2.68 - 2.58 (m, 2H).

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100716, 2014, A1 Location in patent: Paragraph 00232

17
6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide [ No CAS ]
[ 200064-13-7 ]
6-(5-morpholino-3-pyridyl)-3,4-dihydro-2H-1,8-naphthyridine-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 90℃; for 1h; Sealed tube; Inert atmosphere;	57 Synthesis of 6-(5-morpholino-3-pyridyl)-3,4-dihydro-2H-1,8-naphthyridine-1-carboxamide (Compound 90, Table 1) In a sealed tube which contains the crude 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (generated according to the procedure for Step 3 of Example 16 in 5 ml 1,4-dioxane, 0.78 mmol) is added 4-(5-bromo-pyridin-3-yl)-morpholine (228 mg, 0.94 mmol), Na2CO3 (166 mg, 1.56 mmol) and water (1.0 ml). The mixture is bubbled with Argon for 5 min. Then PdCl2(DPPF) DCM complex (64 mg, 0.078 mmol) is added. The mixture is then bubbled with Argon for 5 min. The cap is sealed and the mixture is heated at 90° C. in oil bath for 1 h. The reaction mixture is cooled to room temperature. The reaction mixture is filtered through diatomaceous earth and washed with DCM. The filtrate is partitioned between water and DCM. The aqueous phase is extracted with DCM. The combined DCM phases are concentrated. The crude is purified by flash silica gel column (MeOH/ DCM 0 to 4% gradient, then 4%). The fractions which contain the desired product are combined, concentrated and further purified by C-18 prep HPLC (MeCN with 0.1% TFA/Water with 0.1% TFA, 20 ml/min, 0 to 45% gradient over 10 min run). The desired fractions are combined and basified by 1N Na2CO3 to pH=10, and are extracted by DCM. The DCM phases are combined and concentrated under vacuum to obtain 60 mg of the title compound.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2014/323468, 2014, A1 Location in patent: Paragraph 0543

18
[ 200064-13-7 ]
[ 1008853-90-4 ]

Yield	Reaction Conditions	Operation in experiment
34 mg	With ammonium hydroxide; copper(II) oxide In 1-methyl-pyrrolidin-2-one; dichloromethane at 120℃; for 1h; Microwave irradiation;	0090-1 0090-1 0090-1 A 25% ammonia aqueous solution (2 mL) was added to a mixture of 4-(5-bromopyridin-3-yl)morpholine (447 mg) and copper(I) oxide (130 mg) in N-methylpyrrolidone (2 mL), followed by stirring at 120° C. for 60 minutes using a microwave reaction apparatus. Dichloromethane and water were added to the reaction mixture. The organic layer was collected by separation, and dried over anhydrous sodium sulfate. The obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate), thereby obtaining 5-morpholinopyridine-3-amine (34 mg). MS m/z (M+H): 180.

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US2015/322063, 2015, A1 Location in patent: Paragraph 0802; 0803; 0804

19
1-(3-amino-5-methyl-5H-chromeno[4,3-c]pyridin-8-yl)pyrrolidin-2-one [ No CAS ]
[ 200064-13-7 ]
1-(5-methyl-3-((5-morpholinopyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin-8-yl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine; caesium carbonate In 1,4-dioxane at 100℃; for 18h; Inert atmosphere;	96.2 Step 2: Preparation of l-(5-methyl-3-((5-morpholinopyridin-3-yl)amino)-5H-chromeno[4,3- c]pyridin-8-yl)pynOlidin-2-one To a mixture of Pd2(dba)3 (15 mg, 0.017 mmol) in dioxane (1 mL) was added BrettPhos (18 mg, 0.034 mmol). The resulting mixture was degassed and purged with N2 and then stirred at 50 °C for 10 min. The reaction mixture was cooled to 20 °C and l-(3-amino-5- methyl-5H-chromeno[4,3-c]pyridin-8-yl)pynOlidin-2-one (50 mg, 0.17 mmol), 4-(5- bromopyridin-3-yl)morpholine (54 mg, 0.22 mmol) and CS2CO3 (165 mg, 0.500 mmol) were added and then stirring at 100 °C for 18 h under N2. A black suspension was formed. LCMS showed the starting material was consumed completely and the purity of the desired product (Rt = 0.701 min; MS Calcd: 457.1; MS Found: 458.2 [M+H]+). The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by prep-HPLC (0.05%NH3·H2q as an additive) and lyophilized to give l-(5-methyl-3-((5-morpholinopyridin- 3-yl)amino)-5H-chromeno[4,3-c]pyridin-8-yl)pynOlidin-2-one (27.7 mg, yield: 35%) as an off-white solid. (1289) NMR (400 MHz, DMSO-rie) d 1.52 (3H, d, J= 6.8 Hz), 2.01-2.09 (2H, m), 2.50 (2H, overlap with DMSO), 3.15 (4H, t, J= 4.8Hz), 3.77 (4H, t, J= 4.8 Hz), 3.83 (2H, t , J= 7.6 Hz), 5.26 (1H, q, J= 6.4 Hz), 6.72 (1H, s), 7.30 (1H, dd, J= 8.4, 2.4 Hz), 7.38 (1H, d , J= 2.4 Hz), 7.87 (3H, dd, J= 8.8 Hz, 2.0 Hz), 8.28 (1H, d, J= 2.0 Hz), 8.66 (1H, s), 9.32 (1H, brs).

Reference： [1]Current Patent Assignee: HIBERCELL INC - WO2019/126730, 2019, A1 Location in patent: Paragraph 0461

20
C₁₆H₂₄BNO₄ [ No CAS ]
[ 200064-13-7 ]
4-[5-(morpholin-4-yl)pyridin-3-yl]-2-(propan-2-yloxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In 1,4-dioxane; water Inert atmosphere; Heating;

Reference： [1]Kwiatkowski, Jacek; Liu, Boping; Pang, Shermaine; Ahmad, Nur Huda Binte; Wang, Gang; Poulsen, Anders; Yang, Haiyan; Poh, Yong Rui; Tee, Doris Hui Ying; Ong, Esther; Retna, Priya; Dinie, Nurul; Kwek, Perlyn; Wee, John Liang Kuan; Manoharan, Vithya; Low, Choon Bing; Seah, Peck Gee; Pendharkar, Vishal; Sangthongpitag, Kanda; Joy, Joma; Baburajendran, Nithya; Jansson, Anna Elisabet; Nacro, Kassoum; Hill, Jeffrey; Keller, Thomas H.; Hung, Alvin W. [Journal of Medicinal Chemistry, 2020, vol. 63, # 2, p. 621 - 637]

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 200064-13-7 ]

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[ 200064-13-7 ] Synthesis Path-Downstream 1~20

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Bromides

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Morpholines

Pyridines

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[ 200064-13-7 ]

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