[ CAS No. 209960-29-2 ]

Name: 209960-29-2|2-Fluoro-4-(morpholin-4-yl)aniline|95%
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Product Details of [ 209960-29-2 ]

CAS No. :	209960-29-2	MDL No. :	MFCD09029885
Formula :	C₁₀H₁₃FN₂O	Boiling Point :	368.2±42.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	196.22 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 209960-29-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.53
TPSA :	38.49 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) :	-6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	1.19
Log Po/w (WLOGP) :	1.29
Log Po/w (MLOGP) :	1.24
Log Po/w (SILICOS-IT) :	1.63
Consensus Log Po/w :	1.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.06
Solubility :	1.72 mg/ml ; 0.00876 mol/l
Class :	Soluble
Log S (Ali) :	-1.59
Solubility :	4.99 mg/ml ; 0.0254 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.51
Solubility :	0.611 mg/ml ; 0.00311 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.68

Safety of [ 209960-29-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 209960-29-2 ]

* 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 [ 209960-29-2 ]

[ 209960-29-2 ] Synthesis Path-Downstream 1~32

1
[ 209960-29-2 ]
[ 754193-45-8 ]
[ 855869-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In dichloromethane at 20℃; for 12h;

2
[ 218301-62-3 ]
[ 209960-29-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 5%-palladium/activated carbon; hydrogen In ethanol for 18h;	General procedure for the catalytic reduction of nitrobenzenes 8 and 12. General procedure: Palladium on carbon (5% w/w, 0.30 g) was added to a solution of the appropriate nitrobenzene (7.4 mmol) in ethanol (100 mL) and stirred under hydrogen (1 atm) for 18 h. The mixture was filtered through celite under an argon atmosphere, rinsing with ethanol. The filtrate was concentrated and dried in vacuo affording the crude aniline, which was used without purification.4-Morpholinoaniline 9 (from 8). lavender crystals yield 98%, mp 103.2-103.7 °C. 1H NMR (400 MHz, CDCl3) δ 2.97-3.06 (m, 4H), 3.44 (br s, 2H), 3.81-3.89 (m, 4H), 6.67 (d, J 8.6 Hz, 2H), 6.80 (d, J 9.0 Hz, 2H).2-Fluoro-4-morpholinoaniline (from 12). purple crystals, yield 97%. 1H NMR (400 MHz, CDCl3) δ 2.95-3.05 (m, 4H), 3.78-3.88 (m, 4H), 6.55 (d, J 8.6 Hz, 1H), 6.63 (dd, J 13.5, 2.2 Hz, 1H), 6.72 (t, J 9.4 Hz, 1H).
96%	With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;
50%	With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; Flow reactor;

8.4%	With hydrogen In methanol for 2.5h;
	With hydrogen In methanol for 2h;	224.B 1-(3-amidinophenyl)-3-methyl-5-[(3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl]pyrazole bis-trifluoroacetate Part B. Preparation of N-(3-fluoro-4-aminophenyl)morpholine. N-(3-fluoro-4-nitrophenyl)morpholine (6.01 g,26.59 mmol) and a catalytic amount of palladium on carbon(10%) were suspended in 100 mL methanol in a Parr flask. The reaction mixture was placed on the Parr Hydrogenator at 60psi for 2H. The reaction mixture was passed through a Celite pad and the filtrate was concentrated under reduced pressure to give 4.50 g of N-(3-fluoro-4-aminophenyl)morpholine an off-colored solid. 1H-NMR(DMSO-d6) δ: 6.73 (t,1H, J = 9.34), 6.28 (m,2H), 3.64 (bt, 4H, J = 4.58Hz), 2.76 (bt, 4H, J = 4.58Hz). ESI mass spectrum analysis m/z (relative intensity) 197 (M+H, 100). 19FNMR(DMSO-d6) δ: -124.455.
	With hydrogen In methanol for 2.5h;	29 Preparation of 2-fluoro-4-morpholinoaniline 2-Fluoro-4-morpholinonitrobenzene (1.80 g) was dissolved in methanol (100 mL) and 10% Pd/C (94 mg) was added. The mixture was placed in a hydrogenator (45 psi) for 2.5 h. The reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated to give 1.51 g solid. 1H NMR (CDCl3) δ6.76-6.54 (m, 3H), 3.84 (t, 4H), 3.45 (bs, 2H), 3.02 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 197.1 (M+H, 100).
	With hydrogen In methanol for 2.5h;	29 2-Fluoro-4-morpholinonitrobenzene (1.80 g) was dissolved in methanol (100 mL) and 10% Pd/C (94 mg) was added. The mixture was placed in a hydrogenator (45 psi) for 2.5 h. The reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated to give 1.51 g solid.1H NMR (CDCl3) δ 6.76-6.54 (m, 3H), 3.84 (t, 4H), 3.45 (bs, 2H), 3.02 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 197.1 (M+H, 100).
	With palladium on activated charcoal; hydrogen In methanol
	With palladium on activated charcoal; hydrogen In methanol at 20℃; for 3h;	47.B Step B: Step B: 2-Fluoro-4-morpholine aniline To a solution of 4-(3-fluoro-4-nitrophenyl)morpholine (1.00g, 4.42mmol) in methanol (20mL) was added palladium carbon (517.41mg, 486.20μmol), and it was replaced three times with a hydrogen balloon and then stirred at room temperature for 3 hours. It was filtered with Celite and spin-dried to give the title compound. 1H NMR (400MHz, DMSO-d6) δ=6.73 - 6.63 (m, 2H), 6.54 (dd, J=1.9, 8.4 Hz, 1H), 4.58 (s, 2H), 3.74-3.65 (m, 4H), 2.97-2.85 (m, 4H).

Reference： [1]Fellowes, Thomas; Hong, Yuning; Lobachevsky, Pavel; Martin, Roger F.; Owyong, Tze Cin; Skene, Colin E.; White, Jonathan M. [Arkivoc, 2022, vol. 2022, # 4]
[2]Cantillo, David; Moghaddam, Mojtaba Mirhosseini; Kappe, C. Oliver [Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4530 - 4542]
[3]Örkényi, Róbert; Éles, János; Faigl, Ferenc; Vincze, Péter; Prechl, Anita; Szakács, Zoltán; Kóti, János; Greiner, István [Angewandte Chemie - International Edition, 2017, vol. 56, # 30, p. 8742 - 8745][Angew. Chem., 2017, vol. 129, # 30, p. 8868 - 8871,4]
[4]Quan, Mimi L.; Lam, Patrick Y. S.; Han, Qi; Pinto, Donald J. P.; He, Ming Y.; Li, Renhua; Ellis, Christopher D.; Clark, Charles G.; Teleha, Christopher A.; Sun, Jung-Hui; Alexander, Richard S.; Bai, Steve; Luettgen, Joseph M.; Knabb, Robert M.; Wong, Pancras C.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1729 - 1744]
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP946508, 2009, B1 Location in patent: Page/Page column 92
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6339099, 2002, B1 Location in patent: Page column 105-106
[7]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP991638, 2005, B1 Location in patent: Page/Page column 46
[8]Location in patent: scheme or table Patil, Sudhakar G.; Bagul, Rahul R.; Swami, Mangesh S.; Kotharkar, Nandini; Darade, Kalpana [Chinese Chemical Letters, 2011, vol. 22, # 8, p. 883 - 886]
[9]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - EP3640247, 2020, A1 Location in patent: Paragraph 0293; 0295

3
[ 209960-29-2 ]
1-(3'-aminobenzisoxazol-5'-yl)-3-trifluoromethyl-5-[(2-fluoro-4-morpholinophenyl)aminocarbonyl]pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: (dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C 2.1: acetoxyhydroxamic acid; potassium tert-butoxide / dimethylformamide / 12 h / 20 °C 2.2: HCl / ethanol / 80 °C

4
[ 446-35-5 ]
[ 209960-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.81 g / tetrahydrofuran / 2 h / 20 °C 2: 8.4 percent / H₂ / Pd/C / methanol / 2.5 h / 2327.17 Torr
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: palladium on activated charcoal; hydrogen / methanol
	Multi-step reaction with 2 steps 1: ethanol / 0.17 h / 100 °C / 7500.75 Torr / Flow reactor 2: hydrogen; palladium 10% on activated carbon / ethanol / 50 °C / 760.05 Torr / Flow reactor

Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 80 °C 1.2: 16 h / 20 °C 2.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 20 °C

Reference： [1]Quan, Mimi L.; Lam, Patrick Y. S.; Han, Qi; Pinto, Donald J. P.; He, Ming Y.; Li, Renhua; Ellis, Christopher D.; Clark, Charles G.; Teleha, Christopher A.; Sun, Jung-Hui; Alexander, Richard S.; Bai, Steve; Luettgen, Joseph M.; Knabb, Robert M.; Wong, Pancras C.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1729 - 1744]
[2]Patil, Sudhakar G.; Bagul, Rahul R.; Swami, Mangesh S.; Kotharkar, Nandini; Darade, Kalpana [Chinese Chemical Letters, 2011, vol. 22, # 8, p. 883 - 886]
[3]Örkényi, Róbert; Éles, János; Faigl, Ferenc; Vincze, Péter; Prechl, Anita; Szakács, Zoltán; Kóti, János; Greiner, István [Angewandte Chemie - International Edition, 2017, vol. 56, # 30, p. 8742 - 8745][Angew. Chem., 2017, vol. 129, # 30, p. 8868 - 8871,4]
[4]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - EP3640247, 2020, A1

Yield	Reaction Conditions	Operation in experiment
		224.B 1-(3-amidinophenyl)-3-methyl-5-[(3-fluoro-4-(N-morpholino)phenyl) aminocarbonyl]pyrazole bis-trifluoroacetate Part B. Preparation of N-(3-fluoro-4-aminophenyl)morpholine. N-(3-fluoro-4-nitrophenyl)morpholine (6.01 g,26.59 mmol) and a catalytic amount of palladium on carbon(10%) were suspended in 100 mL methanol in a Parr flask. The reaction mixture was placed on the Parr Hydrogenator at 60 psi for 2 H. The reaction mixture was passed through a Celite pad and the filtrate was concentrated under reduced pressure to give 4.50 g of N-(3-fluoro-4-aminophenyl)morpholine an off-colored solid. 1 H-NMR(DMSO-d6) δ: 6.73 (t, 1 H, J=9.34), 6.28 (m, 2 H), 3.64 (bt, 4 H, J=4.58 Hz), 2.76 (bt, 4 H, J=4.58 Hz). ESI mass spectrum analysis m/z(relative intensity) 197 (M+H, 100). 19 FNMR(DMSO-d6) δ: -124.455.

6
[ 110-91-8 ]
[ 367-24-8 ]
[ 209960-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate	A 1-(3-amidinophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl)pyrazole bis-trifluoro acetate and 1-(3-Carboxamidophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl) pyrazole Part A. Preparation of 2-fluoro-4-(-N-morpholino)aniline. Morpholine(10.0 mL,115 mmol) was added to a mixture of 4-bromo-2-fluoroaniline(1.03 g,5.42 mmol), copper(I) bromide (0.039 g,0.27 mmol) and potassium carbonate(1.50 g,10.84 mmol). The reaction mixture was heated to 130° C. for 48 h, concentrated under reduced pressure and purified by flash chromotography to afford 0.11 g of pure 2-fluoro-4-(-N-morpholino)aniline. 1 H-NMR(DMSO-d6) δ: 6.73 (dd, 1 H, J1 =8.8 Hz, J2 =9.9 Hz), 6.64 (dd, 1 H, J1 =2.6 Hz, J2 =13.2 Hz), 6.57 (m, 1 H), 3.85 (m, 4 H), 3.02 (m, 4 H). ESI mass spectrum analysis m/z(relative intensity) 197 (M+H, 100). 19 FNMR (dmso-d6,300 MHz) δ: -133.
	With potassium carbonate at 130℃; for 48h;	230.A; 231.A 1-(3-amidinophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phanyl)aminocarbonyl)pyrazole bis-trifluoro acetate and 1-(3-Carboxamidophonyl)-3-trifluoramethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl) pyrazole Part A. Preparation of 2-fluoro-4-(-N-morpholino)aniline. Morpholine(10.0 mL,115 mmol) was added to a mixture of 4-bromo-2-fluoroaniline(1.03 g, 5.42 mmol), copper(I) bromide (0.039 g,0.27 mmol) and potassium carbonate(1.50 g,1.0.84 mmol). The reaction mixture was heated to 130°C for 48h, concentrated under reduced pressure and purified by flash chromotography to afford 0.11 g of pure 2-fluoro-4-(-N-morpholino) aniline. 1H-NMR(DMSO-d6) δ: 6.73 (dd, 1H, J1 = 8.8Hz, J2 = 9.9Hz), 6.64 (dd, 1H, J1 = 2.6Hz, J2 = 13.2Hz), 6.57 (m,1H), 3.85 (m,4H), 3.02 (m,4H). ESI mass spectrum analysis m/z(relative intensity) 197 (M+H, 100). 19FNMR (dmso-d6,300MHz) δ: -133.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6020357, 2000, A
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP946508, 2009, B1 Location in patent: Page/Page column 94

7
[ 209960-29-2 ]
[ 754193-45-8 ]
[ 76-05-1 ]
[ 127-06-0 ]
[ 218299-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-(3-fluoro-4-aminophenyl)morpholine; 2-(3-cyano-4-fluoro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride With dmap Stage #2: acetone oxime With sodium t-butanolate Stage #3: trifluoroacetic acid With hydrogenchloride more than 3 stages;	29 Preparation of 1-(3'-Aminobenzisoxazol-5'-yl)-3-trifluoromethyl-5-[(3-fluoro-4-morpholinophenyl)aminocarbonyl]pyrazole The title compound was prepared from 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-pyrazolecarboxylic acid and 2-fluoro-4-morpholinoaniline as a TFA salt by the same procedures described in Example 26. 1H NMR (DMSO-d6) δ9.39 (s, 1H), 8.06 (d, 1H), 7.77-7.48 (m, 4H), 6.81-6.75 (m, 2H), 3.77 (t, 4H), 3.15 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 491.2 (M+H, 100).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6339099, 2002, B1 Location in patent: Page column 106

8
[ 209960-29-2 ]
C₁₃H₉ClFN₃O [ No CAS ]
[ 76-05-1 ]
[ 127-06-0 ]
[ 218299-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-(3-fluoro-4-aminophenyl)morpholine; C₁₃H₉ClFN₃O With dmap Stage #2: acetone oxime With sodium t-butanolate Stage #3: trifluoroacetic acid With hydrogenchloride more than 3 stages;	44 Example 44 1-(3'-Aminobenzisoxazol-5'-yl)-3-ethyl-5-[(2-fluoro-4-morpholinophenyl)aminocarbonyl]pyrazole The title compound was prepared in an analogous fashion as TFA salt. 1H NMR (acetone-d6) δ9.08 (s, 1H), 7.94 (d, 1H), 7.64 (m, 2H), 7.47 (d, 1H), 6.92 (s, 1H), 6.78 (m, 2H), 4.07 (bs, 2H), 3.77 (t, 4H), 3.1 (t, 4H), 2.70 (q, 2H), 1.28 (t, 3H) ppm. ESI mass spectrum z (rel. intensity) 451.2 (M+H, 100).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6339099, 2002, B1 Location in patent: Page column 111

9
[ 209960-29-2 ]
[ 209917-95-3 ]
[ 209960-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In dichloromethane at 20℃; for 72h;	224.C 1-(3-amidinophenyl)-3-methyl-5-[(3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl]pyrazole bis-trifluoroacetate Part C. Preparation of 1-(3-cyanophenyl)-3-methyl-5-((3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl)pyrazole. Dimethylaminopyridine(0.28 g,2.25 mmol) was added to a solution of 1-(3-cyanophenyl)-3-methyl-pyrazole-5-carboxylic acid chloride (0.46 g,1.88 mmol) and N-(3-fluoro-4-aminophenyl)morpholine (0.37 g,1.88 mmol) in 20 mL methylene chloride. The reaction mixture was stirred at ambient temperature for 72H and then concentrated under reduced pressure. The resulting residue was purified via flash chromotography to give 0.070 g of pure 1-(3-cyanophenyl)-3-methyl-5-((3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl)pyrazole. 1H-NMR(DMSO-d6) δ: 10.50 (s,1H) 7.93 (s,1H), 7.83 (d,1H, J = 7.33Hz), 7.73 (d, 1H, J = 8.79Hz), 7.62 (t, 1H, J = 7.87Hz), 7.53 (m,1H), 7.34 (d, 1H, J = 9.15Hz), 6.99 (t, 1H, J = 9.34Hz), 6.93 (s,1H), 3.69 (bt, 4H, J = 4.58Hz), 2.92 (bt, 4H, J = 4.58Hz), 2.28 (s,3H). ESI mass spectrum analysis m/z(relative intensity) 406 (M+H, 100), 833 (2M+Na). 19F NMR (dmso-d6,300MHz) δ: -122.081.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP946508, 2009, B1 Location in patent: Page/Page column 92

10
[ 209960-29-2 ]
N-(3-cyanophenyl)-3-trifluoromethyl-pyrazole-5-carboxylic acid chloride [ No CAS ]
[ 209960-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In dichloromethane at 20℃; for 20h;	230.B; 231.B 1-(3-amidinophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phanyl)aminocarbonyl)pyrazole bis-trifluoro acetate and 1-(3-Carboxamidophonyl)-3-trifluoramethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl) pyrazole Part B. Preparation of 1-(3-cyanophenyl)-3-trifluoromethyl-5-((2'-fluoro-4'-(N-morpholino)phenyl)aminocarbonyl)pyrazole. 2-Fluoro-4-(N-morpholino)aniline(0.11 g,0.56 mmol) in 5 mL methylene chloride was dripped into a stirring solution of N-(3-cyanophenyl)-3-trifluoromethyl-pyrazole-5-carboxylic acid chloride(0.17 g,0.56 mmol) and dimethylaminopyridine (0.082 g, 0.67 mmol) in 10 mL methylene chloride. The reaction mixture was stirred at ambient temperature for 20h. The reaction mixture was concentrated under reduced pressure and purified by flash chromatography to give 0.19 g of pure 1-(3-cyanophenyl)-3-trifluoromethyl-5-[(2'-fluoro-4'-(N-morpholino)phenyl)aminocarbonyl]pyrazole. 1H-NMR(DMSO-d6)δ:7.94 (m, 1H), 7.86 (s,1H), 7.77 (m,3H), 7.61 (dd, 2H, J1 = 7.7Hz, J2 = 8.1Hz), 7.12 (s,1H), 3.85 (m,4H), 3.14 (m,4H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP946508, 2009, B1 Location in patent: Page/Page column 94

11
[ 209960-29-2 ]
[ 1313809-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C