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[ CAS No. 859538-41-3 ]

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Chemical Structure| 859538-41-3

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Quality Control of [ 859538-41-3 ]

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Product Details of [ 859538-41-3 ]

CAS No. :	859538-41-3	MDL No. :	MFCD18256209
Formula :	C₇H₅F₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	173.12 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 859538-41-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 859538-41-3 ]

* 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.

Downstream synthetic route of [ 859538-41-3 ]

[ 859538-41-3 ] Synthesis Path-Downstream 1~9

1
[ 1221272-81-6 ]
[ 859538-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / dimethyl sulfoxide / 24 h / 60 °C / 31029.7 Torr 2.1: sodium hydroxide / ethanol / 5 h / 0 - 20 °C 2.2: pH 4
	Multi-step reaction with 2 steps 1.1: triethylamine / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / dimethyl sulfoxide / 24 h / 60 °C / 31029.7 Torr / autoclave 2.1: lithium hydroxide / ethanol / 5 h / 0 - 20 °C 2.2: pH ~ 4

Reference： [1]Current Patent Assignee: SIENA BIOTECH S.P.A. SOCIETA' IN LIQUIDAZIONE; ROCHE HOLDING AG - US2011/312937, 2011, A1
[2]Current Patent Assignee: SIENA BIOTECH S.P.A. SOCIETA' IN LIQUIDAZIONE; ROCHE HOLDING AG - WO2011/138293, 2011, A1

2
[ 1346148-42-2 ]
[ 859538-41-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester With lithium hydroxide In ethanol at 0 - 20℃; for 5h; Stage #2: With citric acid In water	108.b A solution of 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester (700 mg, 3.7 mmol) in ethanol (8.0 ml) was treated with a solution of sodium hydroxide (5M, 1.5 ml) at 0 °C. Then the reaction mixture was allowed to attain room temperature and was stirred for 5 hours. For the workup, ethanol was removed at reduced pressure. The resulting solid was dissolved in water (5 ml) and the solution was washed with ethyl acetate (2 x 5 ml). The aqueous layer acidified with a solution of citric acid (10%, pH~4), followed by extraction with a 7:3-mixture of dichloromethane and methanol (5 x 10 ml). The combined organic layers were washed with brine (20 ml), dried over sodium sulphate, and evaporated at reduced pressure. The 5- difluoromethyl-pyridine-2-carboxylic acid was obtained as a white solid (400 mg, 62%> of theory).
62%	Stage #1: 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester With sodium hydroxide In ethanol at 0 - 20℃; for 5h; Stage #2: With citric acid In water	108.b b) 5-Difluoromethyl-pyridine-2-carboxylic acidA solution of 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester (700 mg, 3.7 mmol) in ethanol (8.0 ml) was treated with a solution of sodium hydroxide (5M, 1.5 ml) at 0° C. Then the reaction mixture was allowed to attain room temperature and was stirred for 5 hours. For the workup, ethanol was removed at reduced pressure. The resulting solid was dissolved in water (5 ml) and the solution was washed with ethyl acetate (2×5 ml). The aqueous layer acidified with a solution of citric acid (10%, pH4), followed by extraction with a 7:3-mixture of dichloromethane and methanol (5×10 ml). The combined organic layers were washed with brine (20 ml), dried over sodium sulphate, and evaporated at reduced pressure. The 5-difluoromethyl-pyridine-2-carboxylic acid was obtained as a white solid (400 mg, 62% of theory).

Reference： [1]Current Patent Assignee: SIENA BIOTECH S.P.A. SOCIETA' IN LIQUIDAZIONE; ROCHE HOLDING AG - WO2011/138293, 2011, A1 Location in patent: Page/Page column 175
[2]Current Patent Assignee: SIENA BIOTECH S.P.A. SOCIETA' IN LIQUIDAZIONE; ROCHE HOLDING AG - US2011/312937, 2011, A1 Location in patent: Page/Page column 83-84

4
[ 149806-06-4 ]
[ 859538-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; ethyl acetate; n-heptane 2: n-heptane; toluene 3: hydrogenchloride / liquid HCl
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride; water / 1.5 h / 110 °C
	Multi-step reaction with 3 steps 1: ethyl acetate; N,N-dimethyl-formamide; n-heptane 2: toluene; n-heptane 3: hydrogenchloride / liquid HCl

	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride / water / 15 h / 110 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride; water / 1.5 h / 110 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 16 h / 25 °C 3: hydrogenchloride; water / 2.5 h / 110 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride / water / 1.5 h / 110 °C

Reference： [1]Current Patent Assignee: AMGEN INC - US2014/107109, 2014, A1
[2]Current Patent Assignee: AMGEN INC - US2014/213581, 2014, A1
[3]Current Patent Assignee: AMGEN INC - US2014/249104, 2014, A1
[4]Current Patent Assignee: AMGEN INC - WO2014/138484, 2014, A1
[5]Current Patent Assignee: AMGEN INC - US2015/38497, 2015, A1
[6]Current Patent Assignee: MERCK & CO INC - US2015/307465, 2015, A1
[7]Current Patent Assignee: AMGEN INC - WO2016/22724, 2016, A1

5
[ 131747-68-7 ]
[ 859538-41-3 ]

Reference： [1]Patent: US2014/107109,2014,A1
[2]Patent: US2014/213581,2014,A1
[3]Patent: US2014/249104,2014,A1
[4]Patent: WO2014/138484,2014,A1
[5]Patent: US2015/38497,2015,A1
[6]Patent: US2015/307465,2015,A1
[7]Patent: WO2016/22724,2016,A1

6
[ 1211540-57-6 ]
[ 859538-41-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; water at 110℃; for 1.5h;	16.3 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H)
100%	With hydrogenchloride; water at 110℃; for 1.5h;	26.3 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H).
100%	With hydrogenchloride In water at 110℃; for 1.5h;	3 Step 3: 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl) picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110°C for 1.5 h. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z = 174 (M+H) +.

	In hydrogenchloride liquid HCl;	16.3 Step 3: Step 3: 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H).
	In hydrogenchloride liquid HCl;	240.3 Step 3: Step 3: 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H).
	With hydrogenchloride In water at 110℃; for 15h;	12.3 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl) picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110°C for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESf ) m/z = 174 (M+H) +
	With hydrogenchloride; water at 110℃; for 2.5h;	3 Step 3: (0583) 5-(Difluoromethyl)picolinonitrile (118 mg, 0.75 mmol) in 9 mL of conc. HCl was heated at 110° C. for 2.5 h. The mixture was cooled, concentrated and treated with diisopropylethylamine (2 mL). The mixture was re-concentrated and dried in vacuo to give 5-(difluoromethyl)picolinic acid that was used without purification.

Reference： [1]Current Patent Assignee: AMGEN INC - US2014/213581, 2014, A1 Location in patent: Paragraph 0644; 0647
[2]Current Patent Assignee: AMGEN INC - US2015/38497, 2015, A1 Location in patent: Paragraph 0807; 0810
[3]Current Patent Assignee: AMGEN INC - WO2016/22724, 2016, A1 Location in patent: Page/Page column 320
[4]Current Patent Assignee: AMGEN INC - US2014/107109, 2014, A1 Location in patent: Page/Page column
[5]Current Patent Assignee: AMGEN INC - US2014/249104, 2014, A1 Location in patent: Page/Page column
[6]Current Patent Assignee: AMGEN INC - WO2014/138484, 2014, A1 Location in patent: Page/Page column 147
[7]Current Patent Assignee: MERCK & CO INC - US2015/307465, 2015, A1 Location in patent: Paragraph 0583

7
[ 859538-41-3 ]
[ 1624604-99-4 ]

Yield	Reaction Conditions	Operation in experiment
		200 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-(difluoromethyl)picolinamide Example 200 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-(difluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method Z, Example 186 above, but using 5-(difluoromethyl)picolinic acid (intermediate 12). MS m/z=465.0 [M+H]+. Calculated for C19H15F7N4O2: 464.34 1H NMR (400 MHz, CHLOROFORM-d) δ=9.97 (br. s., 1H), 8.76 (br. s., 1H), 8.38 (d, J=8.2 Hz, 1H), 8.16-8.02 (m, 2H), 7.15 (br. s., 1H), 6.97-6.62 (m, 1H), 4.13-4.00 (m, 1H), 2.80 (d, J=13.7 Hz, 1H), 1.93 (t, J=13.2 Hz, 1H), 1.67 (br. s., 3H)

Reference： [1]Current Patent Assignee: AMGEN INC - US2014/249104, 2014, A1 Location in patent: Page/Page column

8
[ 859538-41-3 ]
[ 1624605-20-4 ]

Yield	Reaction Conditions	Operation in experiment
		221 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluoro-5-methylphenyl)-5-(difluoromethyl)picolinamide Example 221 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluoro-5-methylphenyl)-5-(difluoromethyl)picolinamide The title compound was synthesized by procedure and steps analogous to those described in Method A3, Example 216 above, but using 5-(difluoromethyl)picolinic acid (intermediate 12) in step 10. MS m/z=478.9 [M+H]+. Calculated for C20H17F7N4O2: 478.12. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.98 (t, J=12.86 Hz, 1H) 2.26 (d, J=1.90 Hz, 3H) 2.47 (br. s., 1H) 4.28-4.71 (m, 3H) 6.09 (s, 2H) 7.29 (t, J=54.10 Hz, 1H) 7.73 (dd, J=6.65, 2.56 Hz, 1H) 7.82 (dd, J=3.70, 2.80 Hz, 1H) 8.27 (d, J=1.32 Hz, 2H) 8.94 (s, 1H) 10.71 (s, 1H).

Reference： [1]Current Patent Assignee: AMGEN INC - US2014/249104, 2014, A1 Location in patent: Page/Page column

9
[ 859538-41-3 ]
[ 1448793-28-9 ]

Yield	Reaction Conditions	Operation in experiment
		41 Synthesis of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-(difluoromethyl)picolinamide Example 41 Synthesis of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-(difluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method F, Example 32 above, but using 5-(difluoromethyl)picolinic acid. MS m/z=464.9 [M+H]+. Calculated for C19H15F7N4O2: 464.11 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.29 (t, J=13.30 Hz, 1H) 2.77 (dd, J=13.74, 2.63 Hz, 1H) 4.18-4.32 (m, 1H) 4.41-4.87 (m, 2H) 6.90 (m, J=55.98, 1.00, 1.00 Hz, 1H) 7.16 (dd, J=11.40, 8.92 Hz, 1H) 7.61 (dd, J=6.87, 2.48 Hz, 1H) 8.01-8.15 (m, 2H) 8.39 (d, J=8.04 Hz, 1H) 8.78 (s, 1H) 10.02 (s, 1H).

Reference： [1]Current Patent Assignee: AMGEN INC - US2014/249104, 2014, A1 Location in patent: Page/Page column

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Ghs Precautionary Statements

Precautionary Statements-General
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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