[ CAS No. 1310351-03-1 ] {[proInfo.proName]}

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Quality Control of [ 1310351-03-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1310351-03-1 ]

CAS No. :	1310351-03-1	MDL No. :	MFCD29054276
Formula :	C₆H₆F₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	176.12	Pubchem ID :	-
Synonyms :

Safety of [ 1310351-03-1 ]

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Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
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Application In Synthesis of [ 1310351-03-1 ]

* 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 [ 1310351-03-1 ]
Downstream synthetic route of [ 1310351-03-1 ]

[ 1310351-03-1 ] Synthesis Path-Upstream 1~1

1
[ 1310351-03-1 ]
[ 1310350-99-2 ]

Reference： [1] Patent: US2011/144097, 2011, A1,
[2] Patent: WO2011/69934, 2011, A1,
[3] Patent: US2012/184540, 2012, A1,
[4] Patent: US2011/312937, 2011, A1,
[5] Patent: US2012/35195, 2012, A1,
[6] Patent: WO2012/19966, 2012, A1,
[7] Patent: WO2012/98064, 2012, A1,
[8] Patent: US2012/238548, 2012, A1,
[9] Patent: WO2012/126791, 2012, A1,
[10] Patent: US2012/295900, 2012, A1,
[11] Patent: WO2012/156284, 2012, A1,
[12] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3980 - 3995
[13] Patent: WO2011/138293, 2011, A1,

[ 1310351-03-1 ] Synthesis Path-Downstream 1~3

1
[ 67-56-1 ]
[ 925179-02-8 ]
[ 1310351-03-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid; at 0℃; for 2h;Reflux;	a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester A solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C. and treated with sulphuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours. For the workup, the solution was cooled and concentrated at reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and water (30 ml). The organic layer was separated, washed with water until the water phase showed a neutral pH. After drying over sodium sulphate, the organic layer was evaporated at reduced pressure. The 1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester was obtained as a colorless liquid (535 mg, 99% of theory) pure enough to be engaged in the next step without further purification. MS (ISP): m/z=177.1 [M+H]+.
99%	With sulfuric acid; at 0℃; for 2h;Reflux;	A solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg,3.1 mmol) in methanol (18 ml) was cooled to 0 C and treated with sulphuric acid (98%, 0.2 ml, 3.1mmol). The mixture was heated to reflux for 2 hours. For the workup, the solution was cooled and concentrated at reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and water (30 ml). The organic layer was separated, washed with water until the water phase showed a neutral pH. After drying over sodium sulphate, the organic layer was evaporated at reduced pressure. The l-difluoromethyl-lH-pyrazole-3-carboxylic acid methyl ester was obtained as a colorless liquid (535 mg, 99% of theory) pure enough to be engaged in the next step without further purification. MS (ISP): m/z = 177.1 [M+H]+.
99%	With sulfuric acid; at 0℃; for 2h;Reflux;	a) l-Difluoromethyl-lH-pyrazole-3-carboxylic acid methyl esterA solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C and treated with sulphuric acid (98%, 0.2 ml, 3.1mmol). The mixture was heated to reflux for 2 hours. For the workup, the solution was cooled and concentrated at reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and water (30 ml). The organic layer was separated, washed with water until the water phase showed a neutral pH. After drying over sodium sulphate, the organic layer was evaporated at reduced pressure. The l-difluoromethyl-lH-pyrazole-3-carboxylic acid methyl ester was obtained as a colorless liquid (535 mg, 99%) pure enough to be engaged in the next step without further purification; (calculated) C6H6F2N202 [176.12]; (found) [M+H]+ = 177

99%	sulfuric acid; In methanol; at 0℃; for 2h;Reflux;	a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester A solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C. and treated with sulphuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours. For the workup, the solution was cooled and concentrated at reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and water (30 ml). The organic layer was separated, washed with water until the water phase showed a neutral pH. After drying over sodium sulphate, the organic layer was evaporated at reduced pressure. The 1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester was obtained as a colorless liquid (535 mg, 99%) pure enough to be engaged in the next step without further purification; (calculated) C6H6F2N2O2 [176.12]; (found) [M+H]+=177.
99%	With sulfuric acid; at 0℃; for 2h;Reflux;	The 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid was obtained as follows:a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl esterA solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C. and treated with sulphuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours. For the workup, the solution was cooled and concentrated at reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and water (30 ml). The organic layer was separated, washed with water until the water phase showed a neutral pH. After drying over sodium sulphate, the organic layer was evaporated at reduced pressure. The 1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester was obtained as a colorless liquid (535 mg, 99% of theory) pure enough to be engaged in the next step without further purification. MS (ISP): m/z=177.1 [M+H]+.
99%	With sulfuric acid; at 0℃; for 2h;Reflux;	The 4-chloro-l-difluoromethyl-lH-pyrazole-3 -carboxylic acid was obtained as follows: a) l-Difluoromethyl-lH-pyrazole-3 -carboxylic acid methyl ester A solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C and treated with sulphuric acid (98%, 0.2 ml, 3. Immol). The mixture was heated to reflux for 2 hours. For the workup, the solution was cooled and concentrated at reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and water (30 ml). The organic layer was separated, washed with water until the water phase showed a neutral pH. After drying over sodium sulphate, the organic layer was evaporated at reduced pressure. The l-difluoromethyl-lH-pyrazole-3-carboxylic acid methyl ester was obtained as a colorless liquid (535 mg, 99% of theory) pure enough to be engaged in the next step without further purification. MS (ISP): m/z = 177.1 [M+H]+.
93%	With sulfuric acid; for 2h;Reflux;	A solution of 1 -(difluoromethyl)-1 /-/-pyrazole-3-carboxylic acid (238 mg, 1 .47 mmol) in methanol (9 mL) was cooled to 0 C and treated with concentrated sulfuric acid (98%, 0.10 mL, 1 .8 mmol). The reaction mixture was heated at reflux for 2 hours, whereupon it was cooled, concentrated in vacuo, and partitioned between ethyl acetate (15 mL) and water (15 mL). The organic layer was washed with water (3 x 10 mL) until the water washes reached pH 4-5, then washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was obtained as a clear, colorless oil. Yield: 241 mg, 1 .37 mmol, 93%. LCMS m/z 177.0 [M+H]+. 1 H NMR (400 MHz, CDCI3) δ 7.89 (d, J=2.7 Hz, 1 H), 7.28 (t, JHF=60.0 HZ, 1 H), 6.99 (d, J=2.6 Hz, 1 H), 3.98 (s, 3H).
	With sulfuric acid; at 0℃; for 2h;Reflux;	A solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C and treated with sulphuric acid (98%, 0.2 ml, 3.1mmol). The mixture was heated to reflux for 2 hours, cooled to 22C and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z = 177.1 [M+H]+.
	With sulfuric acid; at 0℃; for 2h;Reflux;	A solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS925179-O2-8) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C. and treated with sulphuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours, cooled to 22 C. and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z=177.1 [M+H]+.
	With sulfuric acid; at 0℃; for 2h;Reflux;	Example 160(S)-2-Amino-6-{5-[(4-chloro-l-difluoromethyl-lH-pyrazol-3-ylmethyl)-amino]-2-fluoro- phenyl}-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-onea) l-Difluoromethyl-lH-pyrazole-3-carboxylic acid methyl esterA solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C and treated with sulphuric acid (98%, 0.2 ml, 3.1mmol). The mixture was heated to reflux for 2 hours, cooled to 22C and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z = 177.1 [M+H]+.
	With sulfuric acid; at 0℃; for 2h;Reflux;	a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester A solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS [925179-02-8]) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C. and treated with sulfuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours, cooled to 23 C. and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z=177.1 [M+H]+.
	sulfuric acid; for 2h;Reflux;	The 4-chloro-l-difluoromethyl-lH-pyrazole-3 -carbaldehyde was prepared as follows: a) l-Difluoromethyl-lH-pyrazole-3-carboxylic acid methyl esterFA solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS [925179-02-8]) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C and treated with sulfuric acid (98%, 0.2 ml, 3.1mmol). The mixture was heated to reflux for 2 hours, cooled to 23 C and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z = 177.1 [M+H]+.
	With sulfuric acid; at 0℃; for 2h;Reflux;	The 4-chloro-l-difluoromethyl-lH-pyrazole-3-carbaldehyde was prepared as follows: a) l-Difluoromethyl-lH-pyrazole-3-carboxylic acid methyl esterF A solution of l-difluoromethyl-lH-pyrazole-3-carboxylic acid (CAS [925179-02-8]) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C and treated with sulfuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours, cooled to 23 C and concentrated at reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS (ISP): m/z = 177.1 [M+H]+.
	With sulfuric acid; for 2h;Reflux;	a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester A solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS [925179-02-8]) (500 mg, 3.1 mmol) in methanol (18 ml) was cooled to 0 C. and treated with sulfuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours, cooled to 23 C. and concentrated at reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS (ISP): m/z=177.1 [M+H]+.

Reference： [1]Patent: US2011/144097,2011,A1 .Location in patent: Page/Page column 51-52
[2]Patent: WO2011/69934,2011,A1 .Location in patent: Page/Page column 102
[3]Patent: WO2012/98064,2012,A1 .Location in patent: Page/Page column 86
[4]Patent: US2012/184540,2012,A1 .Location in patent: Page/Page column 45
[5]Patent: US2012/258962,2012,A1 .Location in patent: Page/Page column 45
[6]Patent: WO2012/139993,2012,A1 .Location in patent: Page/Page column 85-86
[7]Journal of Medicinal Chemistry,2013,vol. 56,p. 3980 - 3995
[8]Patent: WO2015/155626,2015,A1 .Location in patent: Page/Page column 81
[9]Patent: WO2011/138293,2011,A1 .Location in patent: Page/Page column 177; 178
[10]Patent: US2012/35195,2012,A1 .Location in patent: Page/Page column 68
[11]Patent: WO2012/19966,2012,A1 .Location in patent: Page/Page column 163
[12]Patent: US2012/238548,2012,A1 .Location in patent: Page/Page column 49
[13]Patent: WO2012/126791,2012,A1 .Location in patent: Page/Page column 95-96
[14]Patent: WO2012/156284,2012,A1 .Location in patent: Page/Page column 116-117
[15]Patent: US2012/295900,2012,A1 .Location in patent: Page/Page column 62

2
[ 1310351-03-1 ]
[ 1310350-99-2 ]

Reference： [1]Patent: US2011/144097,2011,A1
[2]Patent: US2011/312937,2011,A1
[3]Patent: WO2012/19966,2012,A1
[4]Patent: WO2012/98064,2012,A1
[5]Patent: US2012/238548,2012,A1
[6]Patent: WO2012/126791,2012,A1
[7]Patent: US2012/295900,2012,A1
[8]Journal of Medicinal Chemistry,2013,vol. 56,p. 3980 - 3995
[9]Patent: WO2011/138293,2011,A1

3
[ 67-56-1 ]
[ 1310350-99-2 ]
[ 1310351-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 0℃; for 2h;Reflux;	a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester A solution of <strong>[1310350-99-2]1-difluoromethyl-1H-pyrazole-3-carboxylic acid</strong> (CAS925179-02-8) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C. and treated with sulphuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours, cooled to 22 C. and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z=177.1 [M+H]+.

Reference： [1]Patent: US2011/312937,2011,A1 .Location in patent: Page/Page column 85

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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. 1310351-03-1 ] {[proInfo.proName]}

Quality Control of [ 1310351-03-1 ]

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Application In Synthesis of [ 1310351-03-1 ]

[ 1310351-03-1 ] Synthesis Path-Upstream 1~1

[ 1310351-03-1 ] Synthesis Path-Downstream 1~3

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