[ CAS No. 364793-82-8 ]

Name: 364793-82-8|4-(3-Bromobenzyl)morpholine|95+%
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SKU: A272566
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Quality Control of [ 364793-82-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 364793-82-8 ]

CAS No. :	364793-82-8	MDL No. :	MFCD00979456
Formula :	C₁₁H₁₄BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DQGAMPWGTUCNGP-UHFFFAOYSA-N
M.W :	256.14	Pubchem ID :	783082
Synonyms :

Calculated chemistry of [ 364793-82-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.12
TPSA :	12.47 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) :	-10.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.85
Log Po/w (XLOGP3) :	-3.17
Log Po/w (WLOGP) :	1.75
Log Po/w (MLOGP) :	2.15
Log Po/w (SILICOS-IT) :	2.96
Consensus Log Po/w :	1.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.38
Solubility :	620.0 mg/ml ; 2.42 mol/l
Class :	Highly soluble
Log S (Ali) :	3.48
Solubility :	767000.0 mg/ml ; 3000.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-3.84
Solubility :	0.0367 mg/ml ; 0.000143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.69

Safety of [ 364793-82-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 364793-82-8 ]

* 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 [ 364793-82-8 ]
Downstream synthetic route of [ 364793-82-8 ]

[ 364793-82-8 ] Synthesis Path-Upstream 1~2

1
[ 73183-34-3 ]
[ 364793-82-8 ]
[ 364794-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2989 - 2992
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 2, p. 196 - 218
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3820 - 3832

2
[ 73183-34-3 ]
[ 364793-82-8 ]
[ 364794-80-9 ]

Reference： [1] Patent: US2002/26052, 2002, A1,

[ 364793-82-8 ] Synthesis Path-Downstream 1~28

1
[ 110-91-8 ]
[ 3132-99-8 ]
[ 364793-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid In ethanol
	With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 3h;
	With sodium cyanoborohydride; acetic acid In ethanol; dichloromethane	R.31 4-(3-Bromobenzyl) morpholine REFERENCE EXAMPLE 31 4-(3-Bromobenzyl) morpholine To a mixture of 5.0 g (27.0 mmol) of 3-bromobenzaldehyde, 2.35 (27.0 mmol) of morpholine and 1.95 g (32.4 mmol) of acetic acid in 100 mL of ethanol was added 2.21 g (35.1 mmol) of sodium cyanoborohydride in portions over 5 minutes. The resulting mixture was stirred at room temperature for 15 hours. After removal of ethanol in vacuo, the residue was partitioned between 40 mL of methylene chloride and 40 mL of saturated aqueous sodium bicarbonate solution. The layers were separated, and the aqueous layer was extracted with 220 mL methylene chloride. The organic layers were combined and extracted with 350 mL of a 1Nhydrochloric acid solution. The combined aqueous solution was neutralized with SN sodium hydroxide, then sodium bicarbonate. The milky aqueous solution was extracted with 3*50 mL methylene chloride, and the combined organic layers were dried over magnesium sulfate. Following removal of the magnesium sulfate by filtration, and removal of methylene chloride in vacuo, 3.5 g of 4-(3-bromobenzyl) morpholine was obtained as a clear oil; 1H NMR (DMSO-d6) δ 7.50 (d, J=1 Hz, 1H), 7.47-7.43 (m, 1H), 7.33-7.26 (m, 2H), 3.57 (t, J=5 Hz, 4H), 3.46 (s, 2H), 2.34 (t, J=5 Hz, 4H); MS (ES) m/z 256.2, 258.1 (M+1). Analysis for C lH14 BrNO: Calcd: C, 51.58;H, 5.51; N, 5.47. Found: C, 51.62;H, 5.27; N, 5.31.

Reference： [1]Berger, Dan; Dutia, Minu; Powell, Dennis; Wissner, Allan; DeMorin, Frenel; Raifeld, Yuri; Weber, Jennifer; Boschelli, Frank [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2989 - 2992]
[2]Moss, Neil; Breitfelder, Steffen; Betageri, Raj; Cirillo, Pier F.; Fadra, Tazmeen; Hickey, Eugene R.; Kirrane, Thomas; Kroe, Rachel R.; Madwed, Jeffrey; Nelson, Richard M.; Pargellis, Christopher A.; Qian, Kevin C.; Regan, John; Swinamer, Alan; Torcellini, Carol [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247]
[3]Current Patent Assignee: PFIZER INC - US2002/26052, 2002, A1

2
[ 73183-34-3 ]
[ 364793-82-8 ]
[ 364794-80-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 179,p. 449 - 469
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2989 - 2992
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 196 - 218
[4]Journal of Medicinal Chemistry,2013,vol. 56,p. 3820 - 3832

3
[ 110-91-8 ]
polymer, degree of polymerization 60; monomer(s): 2-chlorosulfonyl-5-norbornene; ethyl vinyl ether; 3-bromobenzyl alcohol [ No CAS ]
[ 364793-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 40℃;

Reference： [1]Zhang, Mianji; Moore, Joel D.; Flynn, Daniel L.; Hanson, Paul R. [Organic Letters, 2004, vol. 6, # 16, p. 2657 - 2660]

4
[ 2298-07-9 ]
[ 364793-82-8 ]
[ 945537-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(3-bromobenzyl)morpholine With tributyltin chloride; tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: 4-Bromo-1-naphthylamine In 1,4-dioxane at 100℃; for 24h; Further stages.;

Reference： [1]Moss, Neil; Breitfelder, Steffen; Betageri, Raj; Cirillo, Pier F.; Fadra, Tazmeen; Hickey, Eugene R.; Kirrane, Thomas; Kroe, Rachel R.; Madwed, Jeffrey; Nelson, Richard M.; Pargellis, Christopher A.; Qian, Kevin C.; Regan, John; Swinamer, Alan; Torcellini, Carol [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247]

5
[ 364793-82-8 ]
1-[5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl]-3-[4-(3-(morpholin-4-yl-methyl)phenyl)naphthalen-1-yl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Bu₃SnCl; t-BuLi / tetrahydrofuran / -78 °C 1.2: Pd(PPh₃)4 / dioxane / 24 h / 100 °C 2.1: dimethylsulfoxide / 45 °C

6
[ 364793-82-8 ]
4-(2,4-Dichloro-5-methoxyanilino)-7-[3-(4-morpholinylmethyl)-phenyl]-3-quinolinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: PdCl₂dppf*CH₂Cl₂; KOAc / dimethylsulfoxide 2: Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane / 2 h / Heating

7
[ 364793-82-8 ]
4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-morpholinylmethyl]phenyl }-3-quinolinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: PdCl₂dppf*CH₂Cl₂; KOAc / dimethylsulfoxide 2: Pd(PPh₃)4; NaHCO₃ / 1,2-dimethoxy-ethane

8
[ 364793-82-8 ]
(3-(4-Morpholinylmethyl)phenyl)-zinc bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With zinc In tetrahydrofuran for 12h; Heating / reflux;	2 Example 2; Synthesis of (3-(4-Morpholinylmethyl)phenyl) zinc bromide Example 2 Synthesis of (3-(4-Morpholinylmethyl)phenyl) zinc bromide Three equivalents of Rieke zinc (10 grams in 100 mL THF) was added to an oven dried 100 mL 2-neck round bottom flask with condenser, with an atmosphere of argon gas, with a plastic cannula. One equivalent of (3-(4- Morpholinylmethyl)phenyl) bromide was added neat via syringe over one minute. The reaction was heated to reflux for approximately 12 hours, to yield (3-(4-Morpholinylmethyl)phenyl) zinc bromide.

Reference： [1]Current Patent Assignee: RIEKE METALS - US2004/224364, 2004, A1 Location in patent: Page 3

9
[ 73183-34-3 ]
[ 364793-82-8 ]
4-(2,4-Dichloro-5-methoxyanilino)-7-[3-(4-morholinylmethyl) phenyll-3-quinolinecarbonitrile [ No CAS ]
[ 364794-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In water; dimethyl sulfoxide; ethyl acetate; toluene;	EXAMPLE 26 4-(2,4-Dichloro-5-methoxyanilino)-7-[3-(4-morholinylmethyl) phenyll-3-quinolinecarbonitrile To a dry flask under a nitrogen atmosphere was added 200 mg (0.78 mmol) of 4-(3-bromobenzyl) morpholine, 0.218 g (0.86 mmol) of bis(pinacolato) diboron, 230 mg (2.34 mmol) of potassium acetate, 5 mL of dimethylsulfoxide and 32 mg (0.04 mmol) of [1,1'-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane. The reaction mixture was heated at 80 C. for 2 hours. After cooling, the mixture was partitioned between 20 mL of toluene, 40 mL of ethyl acetate and 40 mL of water. The layers were separated and the aqueous layer was further extracted with 30 mL of ethyl acetate. The organic layers were combined and washed with 4*40 mL water. After drying over magnesium sulfate, removal of the solvents gave crude 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl]morpholine as a dark oil.

Reference： [1]Patent: US2002/26052,2002,A1

10
[ 110-91-8 ]
[ 823-78-9 ]
[ 364793-82-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran at 20℃; for 17h;	16 Preparation 16: 4 -(3-Bromobenzyl)morpholine; 1 -Bromo-3-bromomethyIbenzene (16 g, 64 mmol) in dry tetrahydrofuran (30 mL) was treated w ith morpholine (19.5 g, 224 mmol) and the resulting solution stirred at RT for 17 hours. Ethyl acetate (250 mL) was added and washed with water (150 mL). The aqueous layer was basified to pH 14 with 5M sodium hydroxide and saturated with sodium chloride and re -extracted with the organic layer, followed by extraction with ethyl acetate (2x 100 mL). The combined organic extracts were dried (MgSO 4) leaving a yellow oil (16.4 g, 100 %).
80%	With triethylamine In acetonitrile at 20℃; for 3h;
35%	With potassium carbonate In acetonitrile at 20 - 35℃; for 16h;	To a stirred solution of morpholine (0.5 g, 5.8 mmol) in acetonitrile (5 ml) was added K2CO3 (2.4 g, 17.44 mmol), followed by 3-bromobenzyl bromide (1.45 g, 5.8 mmol) at 0°C and the reaction mixture was stirred at 20-35°C for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (2 x 50 ml). The combined organic layers were washed with brine (50 ml), followed by drying over anhydrous Na2S04 and filtering. The filtrate was rotary evaporated to get residue which was purified by column chromatography using a mixture of 5% ethyl acetate/ hexane as an eluent to get the desired compound as a white solid (700 mg, 35%). NMR (400 MHz, DMSO-d6) δ 7.26 (d, J = 8.3 Hz, 2H), 7.19-7.15 (m, 2H), 5.18 (s, 2H), 3.56 (t, J = 4.6 Hz, 4H), 2.58 (t, J = 4.4 Hz, 4H).

	With triethylamine In tetrahydrofuran at 15 - 25℃; for 8h; Inert atmosphere;	52 Intermediate 52 To a suspension of l-bromo-3-bromomethyl-benzene (530 mg, 2.10 mmol) in THF (10 mL) was added morpholine (200 mg, 1.80 mmol) and Et3N (350 mg, 3.5 mmol). The resulting suspension was stirred at room temperature for 8 hours. Water (35 mL) was then added, and the mixture was extracted with EtOAc (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative TLC (petroleum ether / EtOAc: 5/1) to afford the title compound. LRMS (ESI) calc'd. for CnHi5BrNO [M+H]+: 255, found 255. 1H NMR (CDC13, 400MHz): δ 7.51 (s, 1H), 7.40 (d, / = 8.0 Hz, 1H), 7.29 (d, / = 8.0 Hz, 1H), 7.19 (t, J = 8.0 Hz, 1H), 3.66 (m, 4H), 3.47 (s, 2H), 2.41 (m, 4H).
	With triethylamine In tetrahydrofuran at 20℃; for 8h; Inert atmosphere;	4-(3-bromobenzyl)morpholine To a suspension of 1-bromo-3-bromomethyl-benzene (530 mg, 2.1 mmol) in THF (10 mL) was added morpholine (200 mg, 1.8 mmol) and Et3N (350 mg, 3.5 mmol). The resulting suspension was stirred at room temperature for 8 hour. When the LCMS showed the reaction was complete, water (35 mL) was added, and the mixture was extracted with EtOAc (50 mL),dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified bypreparative TLC (petroleum ether / EtOAc: 5/1) to afford compound, 1-43. MS (ESI) calcd. For C,,H,5BrNO [M+H] 255, found 255. ‘H NMR (CDC13, 400MHz): ö 7.51 (s, 1H), 7.40 (d, J= 8 Hz, 1H), 7.29 (d, J= 8 Hz, 1H), 7.19 (t, J = 8 Hz, 1H), 3.66 (m, 4H), 3.47 (s, 2H), 2.41 (m, 4H).
	With potassium carbonate In acetonitrile at 20 - 25℃;

Reference： [1]Current Patent Assignee: PFIZER INC - WO2007/91152, 2007, A1 Location in patent: Page/Page column 46
[2]Ouach, Aziz; Vercouillie, Johnny; Bertrand, Emilie; Rodrigues, Nuno; Pin, Frederic; Serriere, Sophie; Boiaryna, Liliana; Chartier, Agnes; Percina, Nathalie; Tangpong, Pakorn; Gulhan, Zuhal; Mothes, Celine; Deloye, Jean-Bernard; Guilloteau, Denis; Page, Guylene; Suzenet, Franck; Buron, Frederic; Chalon, Sylvie; Routier, Sylvain [European Journal of Medicinal Chemistry, 2019, vol. 179, p. 449 - 469]
[3]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2013/80222, 2013, A1 Location in patent: Page/Page column 35-36
[4]Current Patent Assignee: PHARMARON INC - WO2014/146490, 2014, A1 Location in patent: Page/Page column 83
[5]Current Patent Assignee: PHARMARON INC - WO2014/146246, 2014, A1 Location in patent: Page/Page column 70
[6]Ferguson, Jalisa H.; De Los Santos, Zeus; Devi, Saroja N.; Kaluz, Stefan; Van Meir, Erwin G.; Zingales, Sarah K.; Wang, Binghe [Journal of Enzyme Inhibition and Medicinal Chemistry, 2017, vol. 32, # 1, p. 992 - 1001]

11
(1R*,2S*)-5'-methoxy-2-(3-vinyl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
[ 364793-82-8 ]
(1R*,2S*)-5'-methoxy-2-((E)-3-(3-(moroholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 150℃; for 0.5h; Microwave irradiation; Inert atmosphere;	A133 Example Al 33. (1 R.2S)-5'-methoxy-2-(3-(3-(morpholinomethvnstyrvn-lH-indazol-6- vDspirorcyclopropane- 1 ,3'-indolin]-2'-one 2,2,2-trifluoroacetateTo a mixture of (l R,2S)-5'-methoxy-2-(3-vinyl-lH-indazol-6-yl)spiro [cyclopropane- l,3'-indolin]-2'-one (66 mg, 0.2 mmol), 4-(3-bromobenzyl)morpholine (56 mg, 0.22 mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol) and P(o-tol)3 (6.7 mg, 0.022 mmol) in DMF (2 mL) was added 'Pr2NEt (0.07 mL, 0.4 mmol). The resulting mixture was purged with argon, then microwaved 30 min at 150 0C. The crude mixture was passed through a microfilter then purified by prep-HPLC to give the title compound (50 mg, 40%) as a light yellow foam. NMR indicated 13% branched isomer. Spectral data was identical to that in obtained in Example A 132.

Reference： [1]Current Patent Assignee: UNIVERSITY HEALTH NETWORK - WO2010/115279, 2010, A1 Location in patent: Page/Page column 242-243

12
(1R*,2S*)-2-(3-vinyl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
[ 364793-82-8 ]
(1R*,2S*)-(E)-2-(3-(3-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 125℃; for 2h; Microwave irradiation; Inert atmosphere;	A152 Example Al 52. (l R,2S)-(E)-2-(3-(3-(morpholinomethyl)styryl)-l H-indazol-6-yl)spiro [cyclopropane-l ,3'-indolin1-2'-one 2,2.2-trifluoroacetateTo a mixture of (l R,2S)-2-(3-vinyl-l H-indazol-6-yl)spiro[cyclopropane-l,3'-indolin]- 2'-one (60.2 mg, 0.2 mmol) and 4-(3-bromobenzyl)morpholine (51.2 mg, 0.2 mmol) in DMF (1.5 mL) was added 1Pr2NEt (0.07 mL), followed by Pd(OAc)2 (2.2 mg, 0.01 mmol) and P(o-tol)3 (6.7 mg, 0.022 mmol). The resulting mixture was purged with argon, and then microwaved 2 h at 125 0C. Purification by prep-HPLC gave the title compound as a white solid (22 mg, 19%). NMR indicated 3% branched isomer. Spectral data was identical to that in obtained in Example A151.
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 125℃; for 2h; Microwave irradiation; Inert atmosphere;	A152 Example A 152. ( 1 R.2S)-(E)-2-(3-(3-(morpholinomethyl)styryl)- 1 H-indazol-6-yl)spiro[00279] To a mixture of ( 1 R,2S)-2-(3-vinyl- 1 H-indazol-6-yl)spiro[cyclopropane- 1 ,3'- indolin]-2'-one (60.2 mg, 0.2 mmol) and 4-(3-bromobenzyl)morpholine (51 .2 mg, 0.2 mmol) in DMF (1.5 mL) was added 'Pr2NEt (0.07 mL), followed by Pd(OAc)2 (2.2 mg, 0.01 mmol) and P(o-tol)3 (6.7 mg, 0.022 mmol). The resulting mixture was purged with argon, and then microwaved 2 h at 125 °C. Purification by prep-HPLC gave the title compound as a white solid (22 mg, 19%). NMR indicated 3% branched isomer. Spectral data was identical to that in obtained in Example A151.

Reference： [1]Current Patent Assignee: UNIVERSITY HEALTH NETWORK - WO2010/115279, 2010, A1 Location in patent: Page/Page column 254
[2]Current Patent Assignee: UNIVERSITY HEALTH NETWORK - WO2011/123946, 2011, A1 Location in patent: Page/Page column 117

13
(1R*,2S*)-5'-methoxy-2-(3-vinyl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
[ 364793-82-8 ]
(1R*,2S*)-5'-methoxy-2-(3-(3-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 150℃; for 0.5h; Microwave irradiation; Inert atmosphere;	A133 Example A133. (lR,2S)-5'-methoxy-2-(3- 3- moφholinomethvnstyrvn-lH-indazol-6- yl)spiro\|cyclopropane- 1 ,3'-indolin\|-2'-one 2,2.2-trifluoroacetate[00273] To a mixture of (lR,2S)-5'-methoxy-2-(3-vinyl-lH-indazol-6-yl)spiro[cyclopropane- l ,3'-indolin]-2'-one (66 mg, 0.2 mmol), 4-(3-bromobenzyl)morpholine (56 mg, 0.22 mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol) and P(o-tol)3 (6.7 mg, 0.022 mmol) in DMF (2 mL) was added 'Pr2NEt (0.07 mL, 0.4 mmol). The resulting mixture was purged with argon, then microwaved 30 min at 150 °C. The crude mixture was passed through a microfilter then purified by prep-HPLC to give the title compound (50 mg, 40%) as a light yellow foam. NMR indicated 13% branched isomer. Spectral data was identical to that in obtained in Example A 132.

Reference： [1]Current Patent Assignee: UNIVERSITY HEALTH NETWORK - WO2011/123946, 2011, A1 Location in patent: Page/Page column 113-114

14
(1R*,2S*)-2-(3-vinyl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
[ 364793-82-8 ]
(1R*,2S*)-(E)-2-(3-(3-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one 2,2,2-trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 2 h / 125 °C / Microwave irradiation; Inert atmosphere 2: water; acetonitrile

Reference： [1]Current Patent Assignee: UNIVERSITY HEALTH NETWORK - WO2011/123946, 2011, A1

15
(1R*,2S*)-5'-methoxy-2-(3-vinyl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one [ No CAS ]
[ 364793-82-8 ]
(1R*,2S*)-5'-methoxy-2-((E)-3-(3-(moroholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one 2,2,2-trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 0.5 h / 150 °C / Microwave irradiation; Inert atmosphere 2: water; acetonitrile

Reference： [1]Current Patent Assignee: UNIVERSITY HEALTH NETWORK - WO2011/123946, 2011, A1

16
[ 364793-82-8 ]
[ 1432450-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; 1,4-dioxane / 12 h / 80 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; ethanol / 12 h / 80 °C

Reference： [1]Patel, Gautam; Karver, Caitlin E.; Behera, Ranjan; Guyett, Paul J.; Sullenberger, Catherine; Edwards, Peter; Roncal, Norma E.; Mensa-Wilmot, Kojo; Pollastri, Michael P. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3820 - 3832]

17
[ 364793-82-8 ]
N-(3-(morpholinomethyl)benzyl)cyclobutanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: sodium tetrahydroborate / methanol / 20 - 25 °C / Inert atmosphere

Reference： [1]Ferguson, Jalisa H.; De Los Santos, Zeus; Devi, Saroja N.; Kaluz, Stefan; Van Meir, Erwin G.; Zingales, Sarah K.; Wang, Binghe [Journal of Enzyme Inhibition and Medicinal Chemistry, 2017, vol. 32, # 1, p. 992 - 1001]

18
[ 364793-82-8 ]
3,4-dimethoxy-N-(3-(morpholinomethyl)benzyl)-N-phenylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: sodium tetrahydroborate; indium(III) chloride / acetonitrile / 0.33 h / Inert atmosphere 3.1: potassium carbonate / dichloromethane / 20 - 25 °C

19
[ 364793-82-8 ]
N-cyclobutyl-3,4-dimethoxy-N-(3-(morpholinomethyl)benzyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: sodium tetrahydroborate / methanol / 20 - 25 °C / Inert atmosphere 3.1: potassium carbonate / dichloromethane / 20 - 25 °C

20
[ 364793-82-8 ]
N-(3-(morpholinomethyl)benzyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: sodium tetrahydroborate; indium(III) chloride / acetonitrile / 0.33 h / Inert atmosphere

21
[ 33513-42-7 ]
[ 364793-82-8 ]
[ 446866-83-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 4-(3-bromobenzyl)morpholine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;

22
[ 364793-82-8 ]
(R)-4-((3'-(1-(quinuclidin-3-yl)-1H-1,2,3-triazol-4-yl)[1,1′-biphenyl]-3-yl)methyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / 90 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Ouach, Aziz; Vercouillie, Johnny; Bertrand, Emilie; Rodrigues, Nuno; Pin, Frederic; Serriere, Sophie; Boiaryna, Liliana; Chartier, Agnes; Percina, Nathalie; Tangpong, Pakorn; Gulhan, Zuhal; Mothes, Celine; Deloye, Jean-Bernard; Guilloteau, Denis; Page, Guylene; Suzenet, Franck; Buron, Frederic; Chalon, Sylvie; Routier, Sylvain [European Journal of Medicinal Chemistry, 2019, vol. 179, p. 449 - 469]

23
[ 364793-82-8 ]
(R)-4-(3-(5-(1-(quinuclidin-3-yl)-1H-1,2,3-triazol-4-yl)thiophen-2-yl)benzyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / 90 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation; Sealed tube

24
[ 364793-82-8 ]
(E)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((4-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinolin-3-yl)methyl)-5-(3-(morpholinomethyl)styryl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / toluene / 3 h / Inert atmosphere; Heating 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water; 1,4-dioxane / 6 h / Heating; Inert atmosphere

Reference： [1]Feng, Qiang; Feng, Zhanzhan; He, Hualong; Hu, Xi; Liu, Zhihao; Teng, Fei; Yu, Luoting; Zhang, Qiangsheng [Bioorganic and medicinal chemistry letters, 2020]

25
[ 364793-82-8 ]
(E)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-yl)methyl)-5-(3-(morpholinomethyl)styryl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / toluene / 3 h / Inert atmosphere; Heating 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water; 1,4-dioxane / 6 h / Heating; Inert atmosphere

Reference： [1]Feng, Qiang; Feng, Zhanzhan; He, Hualong; Hu, Xi; Liu, Zhihao; Teng, Fei; Yu, Luoting; Zhang, Qiangsheng [Bioorganic and medicinal chemistry letters, 2020]

26
[ 75927-49-0 ]
[ 364793-82-8 ]
[ 1010104-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Heating;	General procedure for the synthesis of 8 General procedure: Bromoaryl derivatives (5mmol, 1.0 equiv), pinacol vinylboronate (6mmol, 1.2 equiv) and DIEA (20mmol, 2.0 equiv) were dissolved in toluene (10mL), then air was immediately replaced 5 times with nitrogen after the addition of bis(tri-tert-butylphosphine)palladium(0). The reaction mixture stirred at 95 for 3 h. Upon completion of the reaction as determined by TLC, the solvent was removed under reduced pressure. the residue was dissolved in dichloromethane and filtered by diatomite. The filtrate was washed twice with water and concentrated under reduced pressure. The crude compound was purified by column chromatography eluting with ethyl acetate: hexane to afford the desired compound 8 as a liquid. Yield: 60%.

Reference： [1]Feng, Qiang; Feng, Zhanzhan; He, Hualong; Hu, Xi; Liu, Zhihao; Teng, Fei; Yu, Luoting; Zhang, Qiangsheng [Bioorganic and medicinal chemistry letters, 2020]

27
[ 225916-39-2 ]
[ 364793-82-8 ]
C₁₇H₁₈FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With P(t-Bu)3 Palladacycle Gen_. 3; potassium trimethylsilonate In tetrahydrofuran at 23℃; for 0.5h;

Reference： [1]Delaney, Connor P.; Kassel, Vincent M.; Denmark, Scott E. [ACS Catalysis, 2020, vol. 10, # 1, p. 73 - 80]

28
[ 124898-13-1 ]
[ 364793-82-8 ]
4-(3-(perfluoroethyl)benzyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 4,4'-dimethyl-2,2'-bipyridines; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; sodium acetate; N-(adamantan-1-yl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-amine; copper(I) bromide In acetonitrile for 16h; Irradiation;

Reference： [1]Zhao, Xiangbo; MacMillan, David W. C. [Journal of the American Chemical Society, 2020, vol. 142, # 46, p. 19480 - 19486]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 364793-82-8 ]

Quality Control of [ 364793-82-8 ]

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 364793-82-8 ]

Application In Synthesis of [ 364793-82-8 ]

[ 364793-82-8 ] Synthesis Path-Upstream 1~2

[ 364793-82-8 ] Synthesis Path-Downstream 1~28

Related Functional Groups of [ 364793-82-8 ]

Aryls

Bromides

Related Parent Nucleus of [ 364793-82-8 ]

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 364793-82-8 ]

Related Parent Nucleus of
[ 364793-82-8 ]