[ CAS No. 956697-53-3 ] {[proInfo.proName]}

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Quality Control of [ 956697-53-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 956697-53-3 ]

SDS Specification

Alternatived Products of [ 956697-53-3 ]

Product Details of [ 956697-53-3 ]

CAS No. :	956697-53-3	MDL No. :	MFCD16038928
Formula :	C₂₆H₂₆F₃N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VZZJRYRQSPEMTK-CALCHBBNSA-N
M.W :	485.50	Pubchem ID :	24775005
Synonyms :	Erismodegib;LDE225;NVP-LDE225	Chemical Name :	N-(6-(cis-2,6-Dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide

Safety of [ 956697-53-3 ]

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 [ 956697-53-3 ]

* 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 [ 956697-53-3 ]
Downstream synthetic route of [ 956697-53-3 ]

[ 956697-53-3 ] Synthesis Path-Upstream 1~8

1
[ 139301-27-2 ]
[ 956697-53-3 ]

Yield	Reaction Conditions	Operation in experiment
61.1%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water at 130℃; Sealed tube	4- (trifluoromethoxy) phenylboronic acid (254mg, 1.24mmol), 3-bromo -N- [6- (2,6- dimethyl - morpholin-4-yl) - pyridine 3-yl] -4-methyl -benzamide 5 (250mg, 0.62mmol), Pd (PPh 3) 4 (36mg, 0.03mmol), Na 2 CO 3 (2.0Maqueous solution, 1.23mL, 2.4mmol) and a mixture of DME (4.5mL) in a sealed tube and heated at130 ° C overnight. The reaction mixture was diluted with EtOAc and water. Theaqueous layer was extracted with EtOAc. The combined organic layers were washedwith brine and concentrated to give a crude product, which was then purified bypreparative mass triggered HPLC (C 18 column and eluted with 0.05percent TFA in CH 3CN-H 2 O elution) to give N - (6 - ((2S, 6R) -2,6- dimethyl-morpholino)pyridin-3-yl) -2-methyl-4 '- (trifluoromethoxy) biphenyl-3-carboxylic amide(183.5mg, yield 61.1percent).

Reference： [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 47, p. 9562 - 9571
[2] Patent: CN103893184, 2016, B, . Location in patent: Paragraph 0096; 0100
[3] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684

2
[ 4548-45-2 ]
[ 956697-53-3 ]

Reference： [1] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684
[2] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684
[3] Patent: CN103893184, 2016, B,

3
[ 141-91-3 ]
[ 956697-53-3 ]

Reference： [1] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684
[2] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684
[3] Patent: CN103893184, 2016, B,

4
[ 20753-88-2 ]
[ 956697-53-3 ]

Reference： [1] Patent: CN105330658, 2016, A,
[2] Patent: CN105330658, 2016, A,

5
[ 14618-62-3 ]
[ 956697-53-3 ]

Reference： [1] Patent: CN105330658, 2016, A,
[2] Patent: CN105330658, 2016, A,

6
[ 4214-76-0 ]
[ 956697-53-3 ]

Reference： [1] Patent: CN109293649, 2019, A,
[2] Patent: CN109293649, 2019, A,

7
[ 7697-26-9 ]
[ 956697-53-3 ]

Reference： [1] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684

8
[ 139301-27-2 ]
[ 956697-53-3 ]

Reference： [1] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684

[ 956697-53-3 ] Synthesis Path-Downstream 1~13

2
[ 7697-26-9 ]
[ 956697-53-3 ]

Reference： [1]Drugs of the Future,2014,vol. 39,p. 677 - 684

3
3-bromo-N-(6-((2R,6S)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methylbenzamide [ No CAS ]
[ 139301-27-2 ]
[ 956697-53-3 ]

Yield	Reaction Conditions	Operation in experiment
61.1%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 130℃;Sealed tube;	4- (trifluoromethoxy) phenylboronic acid (254mg, 1.24mmol), 3-bromo -N- [6- (2,6- dimethyl - morpholin-4-yl) - pyridine 3-yl] -4-methyl -benzamide 5 (250mg, 0.62mmol), Pd (PPh 3) 4 (36mg, 0.03mmol), Na 2 CO 3 (2.0Maqueous solution, 1.23mL, 2.4mmol) and a mixture of DME (4.5mL) in a sealed tube and heated at130 C overnight. The reaction mixture was diluted with EtOAc and water. Theaqueous layer was extracted with EtOAc. The combined organic layers were washedwith brine and concentrated to give a crude product, which was then purified bypreparative mass triggered HPLC (C 18 column and eluted with 0.05% TFA in CH 3CN-H 2 O elution) to give N - (6 - ((2S, 6R) -2,6- dimethyl-morpholino)pyridin-3-yl) -2-methyl-4 '- (trifluoromethoxy) biphenyl-3-carboxylic amide(183.5mg, yield 61.1%).

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 9562 - 9571
[2]Green Chemistry,2019,vol. 21,p. 6258 - 6262
[3]Patent: CN103893184,2016,B .Location in patent: Paragraph 0096; 0100
[4]Drugs of the Future,2014,vol. 39,p. 677 - 684

4
[ 139301-27-2 ]
[ 956697-53-3 ]

Reference： [1]Drugs of the Future,2014,vol. 39,p. 677 - 684
[2]Green Chemistry,2019,vol. 21,p. 6258 - 6262

5
[ 956697-53-3 ]
N-[6-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-3-pyridinyl]-2-methyl-4’-(trifluoromethoxy)-[1,1‘-biphenyl]-3-carboxamide diphosphate [ No CAS ]

Reference： [1]Drugs of the Future,2014,vol. 39,p. 677 - 684

6
(2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine [ No CAS ]
2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid [ No CAS ]
[ 956697-53-3 ]

Yield	Reaction Conditions	Operation in experiment
93.6%		In a 500 ml four-necked flask equipped with a stirring, thermometer, reflux condenser and exhaust gas absorption device,Add 250 g of 1,2-dichloroethane, 31.5 g (0.11 mol) of 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxylic acid (VI) ,0.05 g of DMF, 17.9 g (0.15 mol) of thionyl chloride, stirred at 55-60 C for 4 hours.Excess chlorosulfoxide and solvent were recovered by distillation under reduced pressure, and the residue acid chloride was dissolved in 100 g of fresh 1,2-dichloroethane (acid chloride solution) and transferred to a constant pressure dropping funnel.In a 500 ml four-necked flask with stirring, thermometer, reflux condenser and exhaust gas absorption device,Add 200 grams of 1,2-dichloroethane,15.2 g (0.11 mol) potassium carbonate, 20.7 g (0.1 mol) of (2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine (V) obtained by the method of Example 5. ),The solution of the acid chloride obtained above was added dropwise at 40-45 C for 2 hours, and then stirred at 45-50 C for 4 hours.The mixture was cooled to 20-25 C, filtered, and the filter cake was washed twice with 1,2-dichloroethane, 50 g each time, and the filtrate was combined. The filtrate was washed twice with saturated aqueous sodium chloride solution, 30 g each time. The organic phase is separated, and the organic phase is distilled under reduced pressure to recover the solvent.To the residue was added 0.5 g of activated carbon, 200 g of isopropanol, and decolorized at 80-82 C for 1 hour.

Reference： [1]Patent: CN109293649,2019,A .Location in patent: Paragraph 0063; 0089-0090
[2]Green Chemistry,2019,vol. 21,p. 6258 - 6262
[3]Drugs of the Future,2014,vol. 39,p. 677 - 684

7
[ 4548-45-2 ]
[ 956697-53-3 ]

Reference： [1]Drugs of the Future,2014,vol. 39,p. 677 - 684
[2]Drugs of the Future,2014,vol. 39,p. 677 - 684
[3]Patent: CN103893184,2016,B
[4]Green Chemistry,2019,vol. 21,p. 6258 - 6262
[5]Green Chemistry,2019,vol. 21,p. 6258 - 6262

8
[ 141-91-3 ]
[ 956697-53-3 ]

9
(2S,6R)-2,6-dimethyl-4-(5-nitropyridin-2-yl)morpholine [ No CAS ]
[ 956697-53-3 ]

10
(2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine [ No CAS ]
[ 956697-53-3 ]

Reference： [1]Drugs of the Future,2014,vol. 39,p. 677 - 684

11
[ 956697-53-3 ]
N-(6-((2R,6S)-2,6-dimethylmorpholino)-2-oxo-1,2-dihydropyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium formate; In water; acetonitrile; for 3.33333h;Electrochemical reaction;	Example 4: Preparation of N-(6-((2R,6S)-2,6-dimethylmorpholino)-2-oxo-1,2- dihydropyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide (Metabolite M43) The compound was prepared by electrochemical oxidation: A Harvard syringe pump (702212B, Harvard Apparatus Holliston, MA) with a Hamilton 5ml syringe was attached to the flow cell (mu-prepcell with magic diamond electrode) controlled by a Roxy potentiostat (Antec, Leyden, Netherlands). A solution of N-(6-((2S,6R)-2,6-dimethylmorpholino)pyridin-3-yl)-2- methyl-4'-(trifluoromethoxy)-[l, -biphenyl]-3-carboxamide (250 muMu) in acetonitrile / aqueous ammonium formiate (pH 7.4; 20 mM) 1 : 1 was introduced to the flow cell at a flow rate of 25 mu / min. A square wave pulse of 1.2 and 1.6 V was applied during 200 minutes.The collected reaction mixture was lyophilized and purified by semiprep RP-HPLC on a Waters Acquity UPLC HSS T3 (1.8muetaiota; 3.0 x 150 mm) column. The pure fraction was lyophilized and submitted without weighing to NMR and HR-MS analysis. HR-MS (m/z, MH+): 502.194471H NMR (600 MHz, DMSO-i/6): delta ppm = 1.13 (d, 6H), 2.23 (s, 3H), 2.31 (t, 2H), 3.62 (m, 2H), 3.75 (m, 2H), 5.80 (m, 1H), 7.29 (d, 1H), 7.35 (t, 1H), 7.4- 7.6 (m, 5H), 7.94 (d, 1H), 9.02 (s br, 1H)

Reference： [1]Patent: WO2015/92720,2015,A1 .Location in patent: Page/Page column 22

12
[ 956697-53-3 ]
N-(6-((2-hydroxypropyl)(2-oxopropyl)amino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant mutant bacterial P450 enzyme MCYP-0032; antifoam 204; In water; acetonitrile; at 30℃; for 20h;Enzymatic reaction;	Example 5: Preparation of N-(6-((2-hydroxypropyl)(2-oxopropyl)amino)pyridin-3-yl)-2- methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide (Metabolite M25) 1.1 g of the recombinant mutant bacterial P450 enzyme MCYP-0032 and 31.5 g of ready to use reaction mixture, both from CODEXIS Inc. (Redwood City, CA, USA), were dissolved in 1300 mL of deionized water. 350 mg of NVP-LDE225 dissolved in a mixture of 20 mL acetonitrile and 10 mL of deionized water as well as 200 muEpsilon of antifoam 204 (Sigma Aldrich) were added. Incubation was performed in portions of 100 mL volume in 500 mL Erlenmeyer flasks without stopper at 30C and 240 rpm in a laboratory shaker with 5 cm stroke radius. After 20 h of incubation the reaction mixture was supplemented with 100 g/L of NaCl and extracted with 2.5 volumes of tert.-butylmethylether for 10 min. 15 g of Isolute H-MN (Separtis AG, Grellingen, Switzerland) was added to the organic phase and the solvent was removed under reduced pressure. The Isolute H-MN was filled into a liquid chromatography precolumn attached to a column (50 x 200 mm) filled with Lichroprep RP-18 (40 - 63 muetaiota) and the products were eluted with a gradient of increasing acetonitrile concentration in water in the presence of 0.05 % TFA. The product containing fractions were further separated by three chromatographic methods on a Waters Autopurification LC/MS instrument: Method 1 : Column Kromasil CN 21 x 250 mm; gradient of 50 - 95 % of acetonitrile in aqueous 0.05 % formic acid. Method 2: Column Waters Sunfire CI 8 19 x 250 mm; gradient of 10 - 45 % of methanol in aqueous 0.4 % isopropylamine, pH 8. Method 3: Waters Sunfire CI 8 19 x 250 mm; gradient of 50 - 95 % of acetonitrile in aqueous 0.05 % formic acid. The organic solvent was removed from the product containing fractions under reduced pressure in a rotary evaporator and afterwards water by lyophilization.0.8 mg of the title compound was obtained with 91 % purity (LC/UV276 nm). LC/MS (m/z, MH ): 5021H NMR (600 MHz, DMSO-d6): delta ppm 1.08 (m, 3H), 2.09 (s, 3H), 2.23 (s, 3H), 2.37 (m, 2H), 4.1 - 4.2 (m, 2H), 4.33 (s, 2H), 6.83 (d, 1H), 7.25 - 7.55 (m, 7H), 7.91 (m, 1H), 8.40 (s, 1H), 10.23 (s, 1H)

Reference： [1]Patent: WO2015/92720,2015,A1 .Location in patent: Page/Page column 22; 23

13
N-(6-aminopyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxamide [ No CAS ]
2R,2'S-bis(1-propanol mathannesulfonate)ether [ No CAS ]
[ 956697-53-3 ]

Yield	Reaction Conditions	Operation in experiment
84.1%	With triethylamine; In ethanol; at 80 - 90℃;	Reaction flask was added cis-2R, 2'S- bis (1-propanol methanesulfonate) ether (IV) (1.74g, 6mmol) , N- (6-amino-pyridin-3-yl) -2- yl-4 '- (trifluoromethoxy) - [1,1'-biphenyl] -3-carboxamide (V) (1.94g, 5mmol) ,triethylamine (1.0g, 10mmol) and ethanol 50mL, was heated to 80-90 , the reaction was stirred 24-28 hours to complete the reaction by TLC.Recovery of the solvent by distillation under reduced pressure, the residue was recrystallized from acetonitrile to give a white solid type Sony Gibb (I) 2.04g, yield% 84.1,

Reference： [1]Patent: CN105330658,2016,A .Location in patent: Paragraph 0014; 0045; 0046

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Isomers

Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

Historical Records

Similar Product of
[ 956697-53-3 ]

A624949[ 1218778-77-8 ]

rel-N-(6-((2R,6S)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide bis(phosphate)

Reason: Free-salt

Ghs Precautionary Statements

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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. 956697-53-3 ] {[proInfo.proName]}

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