[ CAS No. 59303-10-5 ] {[proInfo.proName]}

Name: 59303-10-5|2-Chloro-5-methylpyrazine|97%
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Quality Control of [ 59303-10-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 59303-10-5 ]

CAS No. :	59303-10-5	MDL No. :	MFCD00055039
Formula :	C₅H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XSDAJECCWPYVGW-UHFFFAOYSA-N
M.W :	128.56	Pubchem ID :	12600386
Synonyms :

Calculated chemistry of [ 59303-10-5 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.01
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.53
Log Po/w (XLOGP3) :	1.08
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	0.13
Log Po/w (SILICOS-IT) :	2.04
Consensus Log Po/w :	1.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.87
Solubility :	1.72 mg/ml ; 0.0134 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	7.87 mg/ml ; 0.0612 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.311 mg/ml ; 0.00242 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.93

Safety of [ 59303-10-5 ]

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 [ 59303-10-5 ]

* 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 [ 59303-10-5 ]
Downstream synthetic route of [ 59303-10-5 ]

[ 59303-10-5 ] Synthesis Path-Upstream 1~6

1
[ 822-36-6 ]
[ 67-66-3 ]
[ 38557-71-0 ]
[ 3435-25-4 ]
[ 59303-10-5 ]
[ 54198-82-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

2
[ 822-36-6 ]
[ 67-66-3 ]
[ 38557-71-0 ]
[ 3435-25-4 ]
[ 59303-10-5 ]
[ 54198-82-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

3
[ 59303-10-5 ]
[ 5521-58-4 ]

Reference： [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1580,1582

4
[ 20721-17-9 ]
[ 59303-10-5 ]

Reference： [1] Patent: WO2003/82817, 2003, A2, . Location in patent: Page/Page column 58
[2] Patent: WO2004/80998, 2004, A1, . Location in patent: Page column 28-29

5
[ 20721-17-9 ]
[ 59303-10-5 ]

Reference： [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1580,1582
[2] Patent: EP1422218, 2004, A1, . Location in patent: Page 177; 178

6
[ 822-36-6 ]
[ 67-66-3 ]
[ 38557-71-0 ]
[ 3435-25-4 ]
[ 59303-10-5 ]
[ 54198-82-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

[ 59303-10-5 ] Synthesis Path-Downstream 1~40

1
[ 59303-10-5 ]
[ 5521-58-4 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1580,1582

2
[ 20721-17-9 ]
[ 59303-10-5 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1580,1582
[2]Patent: EP1422218,2004,A1 .Location in patent: Page 177; 178

3
[ 822-36-6 ]
[ 67-66-3 ]
[ 38557-71-0 ]
[ 3435-25-4 ]
[ 59303-10-5 ]
[ 54198-82-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1427 - 1430

5
[ 20721-17-9 ]
[ 59303-10-5 ]

Yield	Reaction Conditions	Operation in experiment
		Step B. 2-Chloro-5-methylpyrazine; A 250-mL round bottom flask was charged with 8.61 g of 2-hydroxy- 5-methylpyrazine from Step A and 50 mL of phosphorus oxychloride. After the addition of 0.2 mL of sulfuric acid, the mixture was heated at reflux for 1 h. An additional 2.5 mL of sulfuric acid was added and the resultant solution was heated at reflux for 14 h, and then concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The aqueous phase was extracted with three portions of ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. Purification by flash chromatography (silica gel, 4: 1 then 1: 1 hexane/ethyl acetate) afforded the title compound as a yellow oil. MS 128.9 (M+1).
		2-HYDROXY-5-METHYLPYRAZINE (0.984g, 8.94 mmol) was refluxed in 15 mL PHOSPHOROXY- chloride for 1.5h. The reaction mixture was slowly poured into ice and adjusted to pH6 by addition of sodium carbonate. The mixture was extracted six times with ethyl acetate (50 mL each). The combined organic extracts were dried with sodium sulfate, filtered and eva- porated. The crude product was used without any further purification for the next step.

Reference： [1]Patent: WO2003/82817,2003,A2 .Location in patent: Page/Page column 58
[2]Patent: WO2004/80998,2004,A1 .Location in patent: Page column 28-29

6
[ 59303-10-5 ]
[ 500370-18-3 ]

Reference： [1]Patent: EP1422218,2004,A1 .Location in patent: Page 177; 178

7
[ 59303-10-5 ]
4-((1r,4r)-4-(4-(methylsulfonyl)phenoxy)cyclohexyloxy)piperidine hydrochloride [ No CAS ]
2-methyl-5-(4-((1r,4r)-4-(4-(methylsulfonyl)phenoxy)cyclohexyloxy)piperidin-1-yl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In isopropyl alcohol; at 200℃; for 5h;microwave irradiation;	A mixture of 4-((lr,4r)-4-(4-(methylsulfonyl)phenoxy)cyclohexyloxy)piperidine hydrochloride (24.2 mg, 0.062 mmol), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (90 mg, 0.700 mmol), and triethylamine (40 mu, 0.287 mmol) in iPrOH (1 mL) was heated under microwave irradiation at 200 C for 5 h. The mixture was concentrated and the residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (8.7 mg) as a white solid. LCMS m/z = 446.2 [M+H]+; .H NMR (400 MHz, CDC13) delta 1.46-1.68 (m, 6H), 1.89-1.96 (m, 2H), 1.99- 2.04 (m, 2H), 2.10-2.15 (m, 2H), 2.39 (s, 3H), 3.03 (s, 3H), 3.21-3.27 (m, 2H), 3.55-3.59 (m, IH), 3.63-3.67 (m, IH), 3.91-3.97 (m, 2H), 4.39-4.44 (m, IH), 6.98-7.01 (m, 2H), 7.83-7.86 (m, 2H), 7.94 (s, IH), 8.07 (s, IH).

Reference： [1]Patent: WO2011/127051,2011,A1 .Location in patent: Page/Page column 167

8
[ 59303-10-5 ]
[ 1382136-68-6 ]
[ 1391081-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In dimethyl sulfoxide; at 150℃;Microwave irardiation;	Example 105-(4-Methanesulfonyl-phenyl)-2-[1 -(5-methyl-pyrazin-2-yl)-piperidin-4-yl1-2,3-dihydro- furo 2,3c]pyridineA mixture of 5-(4-methanesulfonyl-phenyl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3- c]pyridine (50 mg), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (30 mg), and cesium carbonate (91 mg) in dimethylsulfoxide (1 ml_) is heated to 150C in a microwave oven. After cooling to room temperature the reaction mixture is diluted with water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgS04, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 98:2? 97:3). The crude product is triturated with a small amount of methanol and the precipitate is filtered off, washed with diethyl ether, and dried to give the title compound. LC (method 5): tR = 1.08 min; Mass spectrum (EST): m/z = 451 [M+H]+.
	With caesium carbonate; In dimethyl sulfoxide; at 150℃;Microwave irradiation;	A mixture of 5-(4-methanesulfonyl-phenyl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine (50 mg), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (30 mg), and cesium carbonate (91 mg) in dimethylsulfoxide (1 mL) is heated to 150 C. in a microwave oven. After cooling to room temperature the reaction mixture is diluted with water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 98:2?97:3). The crude product is triturated with a small amount of methanol and the precipitate is filtered off, washed with diethyl ether, and dried to give the title compound. LC (method 5): tR=1.08 min; Mass spectrum (ESI+): m/z=451 [M+H]+.

Reference： [1]Patent: WO2012/98217,2012,A1 .Location in patent: Page/Page column 101
[2]Patent: US2013/18030,2013,A1 .Location in patent: Paragraph 0445; 0446

9
[ 59303-10-5 ]
[ 1382137-31-6 ]
[ 1391081-73-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 100℃;	Example 38(S)-5-(1 -Methanesulfonyl-1 ,2,3,6-tetrahvdro-pyridin-4-yl)-2-methyl-2-ri -(5- trifluoromethyl-pyrazin-2-yl)-piperidin-4-yl1-2,3-dihvdro-furo[2,3-clpyridineThe title compound is prepared from (S)-5-(1 -methanesulfonyl-1 ,2,3,6-tetrahydro- pyridin-4-yl)-2-methyl-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine (Intermediate 41 ; the configuration of the stereocenter is arbitrarily assigned) and 2-chloro-5- (trifluoromethyl)pyrazine in dimethylsulfoxide at 100C in the presence of potassium carbonate. LC (method 4): tR = 1 .06 min; Mass spectrum (EST): m/z = 524 [M+H]+.

Reference： [1]Patent: WO2012/98217,2012,A1 .Location in patent: Page/Page column 112

10
[ 59303-10-5 ]
[ 1400706-57-1 ]
[ 1400707-76-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 72h;	Example 61N-Cvclopropyl-N-[1 -(5-methyl-pyrazin-2-yl)-piperidin-4-yl1-4-oxazol-5-yl-benzamide A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide (600 mg), 2- chloro-5-methyl-pyrazine (100 mg), and cesium carbonate (300 mg) in N,N- dimethylformamide (10 ml_) is stirred for 3 days at 80C. After cooling to room temperature ethyl acetate and water are added. The organic phase is separated, washed with water and brine, dried over MgS04, and concentrated in vacuo.The residue is chromatographed on silica gel (ethyl acetate/methanol 7:3) to give the title compound. LC (method 1 ): tR = 1 .08 min; Mass spectrum (EST): m/z = 404[M+H]+.
	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 72h;	A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide (600 mg), <strong>[59303-10-5]2-chloro-5-methyl-pyrazine</strong> (100 mg), and cesium carbonate (300 mg) in N,N-dimethylformamide (10 mL) is stirred for 3 days at 80 C. After cooling to room temperature ethyl acetate and water are added. The organic phase is separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 7:3) to give the title compound. LC (method 1): tR=1.08 min; Mass spectrum (ESI+): m/z=404 [M+H]+.

Reference： [1]Patent: WO2012/123449,2012,A1 .Location in patent: Page/Page column 118-119
[2]Patent: US2013/65906,2013,A1 .Location in patent: Paragraph 0534; 0535

11
[ 59303-10-5 ]
4-(((1r,4r)-4-(2-fluoro-4-(methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride [ No CAS ]
2-(4-(((1r,4r)-4-(2-fluoro-4-(methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-1-yl)-5-methylpyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.7%	With triethylamine; In isopropyl alcohol; at 150 - 200℃; for 16h;Microwave irradiation;	Example 1.18: Preparation of 2-(4-(((lr,4r)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-l-yl)-5-methylpyrazine (Compound 9).; A mixture of 4-(((l r,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride (36.1 mg, 0.089 mmol), prepared in Example 1.17, Step A, <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (25 mg, 0.194 mmol), and triethylamine (50 muEpsilon, 0.359 mmol) in iPrOH (2 mL) was heated under microwave at 150 C for 1 h, at 200 C for 1 h, and then at 180 C for 14 h. The mixture was purified by HPLC (5- 95% CH3CN). Fractions containing the title compound were partly concentrated and the residue was extracted with 1M NaOH and CH2C12 (three times). The combined organic phases were dried over MgS04, filtered, and concentrated to give the title compound (24.1 mg, 0.052 mmol, 58.7 % yield) as a white solid. Exact mass calculated for C24H32FN3O3S: 461.21 , found: LCMS m/z = 462.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.24-1.58 (m, 6H), 1.81-1.96 (m, 5H), 2.17-2.20 (m, 2H), 2.40 (s, 3H), 2.84-2.95 (m, 3H), 3.05 (s, 3H), 3.25-3.31 (m, 1H), 3.37 (d, = 6.2 Hz, 2H), 4.25-4.28 (m, 2H), 7.40-7.43 (m, 1H), 7.58-7.60 (m, 1H), 7.66-7.68 (m, 1H), 7.95 (s, 1H), 8.06 (s, 1H).

Reference： [1]Patent: WO2012/135570,2012,A1 .Location in patent: Page/Page column 117

12
[ 59303-10-5 ]
[ 1407544-52-8 ]
[ 1407544-45-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium t-butanolate; DavePhos;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 120℃; for 0.416667h;Inert atmosphere; Microwave irradiation;	Example 8l-((2S,4R)-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2-methyl-4-((5- methylpyrazin-2-yl)amino)-3, -dihydroquinolin-l(2H)-yl)ethanonel-((2S,4R)-4-Amino-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)ethanone (for a preparation see Intermediate 7) (150mg, 0.457 mmol), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (147mg, 1.142 mmol), Davephos (71.9mg, 0.183 mmol), Pd2(dba)3 (84mg, 0.091 mmol) and sodium tert-butoxide (132mg, 1.370 mmol) were combined in 1,4-dioxane (4ml) and the mixture heated at 120C for 25min (microwave). The reaction mixture was partitioned between water (75ml) and DCM (3x 75ml). The organics were combined, dried (hydrophobic frit) and evaporated under vacuum. The resulting brown oil was dissolved in DMSO (3x 1ml) and purified by MDAP (formate x3). The solvent was evaporated under vacuum to give l-((2S,4R)-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2- methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-l(2H)-yl)ethanone (91mg, 0.216 mmol, 47 % yield) as a yellow glass. LCMS (formate), Rt 0.75min, MH+ 421.
47%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 120℃; for 0.75h;Microwave irradiation;	EXAMPLE 8 1-((2S,4R)-6-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)-2-methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-1(2H)-yl)ethanone 1-((2S,4R)-4-Amino-6-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (for a preparation see Intermediate 7) (150 mg, 0.457 mmol), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (147 mg, 1.142 mmol), Davephos (71.9 mg, 0.183 mmol), Pd2(dba)3 (84 mg, 0.091 mmol) and sodium tert-butoxide (132 mg, 1.370 mmol) were combined in 1,4-dioxane (4 ml) and the mixture heated at 120 C. for 25 min (microwave). The reaction mixture was partitioned between water (75 ml) and DCM (375 ml). The organics were combined, dried (hydrophobic frit) and evaporated under vacuum. The resulting brown oil was dissolved in DMSO (31 ml) and purified by MDAP (formate *3). The solvent was evaporated under vacuum to give 1-((2S,4R)-6-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)-2-methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-1(2H)-yl)ethanone (91 mg, 0.216 mmol, 47% yield) as a yellow glass. LCMS (formate), Rt 0.75 min, MH+421. Reference compound A: 2-methyl-6-(methyloxy)-4H-3,1-benzoxazin-4-one

Reference： [1]Patent: WO2012/150234,2012,A1 .Location in patent: Page/Page column 39
[2]Patent: US2014/66459,2014,A1 .Location in patent: Paragraph 0286-0287

13
[ 59303-10-5 ]
[ 1415836-62-2 ]
[ 1415835-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 200℃; for 0.5h;Microwave irradiation;	Example 192-(2-Methyl-imidazol-1 -yl)-pyrimidine-5-carboxylic acid cvclopropyl-H -(5-methyl- pyrazin-2-yl)-pipehdin-4-vH-amideA mixture of 2-(2-methyl-imidazol-1 -yl)-pyrimidine-5-carboxylic acid cyclopropyl- piperidin-4-yl-amide (44 mg, Intermediate 20), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (15 mg) and ethyldiisopropylamine (35 muIota_) in N-methyl-2-pyrrolidinone (1 .0 ml_) is heated in a microwave oven for 30 min at 200C. After removal of the solvent the residue is purified by HPLC (H2O/MeOH/TFA) to give the title compound. LC (method 3): tR = 0.92 min; Mass spectrum (ESI+): m/z = 419 [M+H]+.
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 200℃; for 0.5h;Microwave irradiation;	Example 19 2-(2-Methyl-imidazol-1-yl)-pyrimidine-5-carboxylic acid cyclopropyl-[1-(5-methyl-pyrazin-2-yl)-piperidin-4-yl]-amide A mixture of 2-(2-methyl-imidazol-1-yl)-pyrimidine-5-carboxylic acid cyclopropyl-piperidin-4-yl-amide (44 mg, Intermediate 20), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (15 mg) and ethyldiisopropylamine (35 muL) in N-methyl-2-pyrrolidinone (1.0 mL) is heated in a microwave oven for 30 min at 200 C. After removal of the solvent the residue is purified by HPLC(H2O/MeOH/TFA) to give the title compound. LC (method 3): tR=0.92 min; Mass spectrum (ESI+): m/z=419 [M+H]+.

Reference： [1]Patent: WO2012/168315,2012,A1 .Location in patent: Page/Page column 123-124
[2]Patent: US2013/143892,2013,A1 .Location in patent: Paragraph 0485; 0486

14
[ 59303-10-5 ]
[ 1433707-80-2 ]

Yield	Reaction Conditions	Operation in experiment
5.52 g	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chlorobenzene; at 130℃; for 4h;	PREPARATION EXAMPLE 2: N-rri -(5-methoxypyrazin-2-vncvclopropyllmethyll-2- (trifluoromethyl)benzamide (compound A.26)Step 1 : 2-(bromomethyl)-5-chloro-pyrazine5.0 g of <strong>[59303-10-5]2-chloro-5-methyl-pyrazine</strong>, 6.9 g of N-bromosuccinimide and 0.33 g of 2,2'- azobis(2-methylpropionitrile) were suspended in 67 ml of chlorobenzene. The yellow mixture was heated to 130C and stirred for 4 hours. Then the mixture was cooled to ambient temperature, diluted with ethyl acetate and an aqueous solution of sodium thiosulfate was added. After extraction the phases were separated, the organic layer was washed with brine, dried over anhydrous sodium sulphate and evaporated. The residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (2:1 ) as eluent. Thus, 5.52 g of 2-(bromomethyl)-5-chloro-pyrazine was obtained as a brown oil. 1H-NMR (CDCI3): 8.57 ppm (s, 1 H), 8.49 ppm (s, 1 H), 4.54 ppm (s, 2H).

Reference： [1]Patent: WO2013/64518,2013,A1 .Location in patent: Page/Page column 84

15
[ 59303-10-5 ]
[ 1433707-71-1 ]

Reference： [1]Patent: WO2013/64518,2013,A1

16
[ 59303-10-5 ]
[ 1433708-16-7 ]

Reference： [1]Patent: WO2013/64518,2013,A1

17
[ 59303-10-5 ]
[ 1433708-19-0 ]

Reference： [1]Patent: WO2013/64518,2013,A1

18
[ 59303-10-5 ]
[ 1433707-33-5 ]

Reference： [1]Patent: WO2013/64518,2013,A1

19
[ 59303-10-5 ]
rac-1-((2S,3R,4R)-4-amino-2-cyclopropyl-3-methyl-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]
rac-1-((2S,3R,4R)-2-cyclopropyl-3-methyl-4-((5-methylpyrazin-2-yl)amino)-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 90℃; for 20h;Inert atmosphere;	A solution of rac- I -((2S,3R,4R)-4-am ino-2-cyclopropyl-3-methyl-6-morpholino-3,4-dihydroqu inolin1(2H)-yl)ethanone (for a preparation see Intermediate 83, 100 mg, 0.304 mmol), DavePhos (11.95mg, 0.030 mmol), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (46.8 mg, 0.364 mmol), Pd2(dba)3 (13.90 mg, 0.015 mmol) and sodium tert-butoxide (58.3 mg, 0.607 mmol) in 1,4-dioxane (3 mL) was stirred under nitrogen at 90 C for 20 h. The reaction mixture was allowed to cool to rt, filtered through celite and rinsed with ethyl acetate. The solvent was evaporated in vacuo then the sample was dissolved in 1:1 MeOH:DMSO (1 mL) and purified by MDAP (HpH). The appropriate fractions were combined andconcentrated in vacuo to give the title compound (36 mg, 0.085 mmol, 28%). LCMS (2 mm Formic): Rt = 0.84 mi [MH] = 422.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 340

20
[ 59303-10-5 ]
rac-1-((2S,3R,4R)-4-amino-2,3-dimethyl-6-(tetrahydro-2H-pyran-4-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]
rac-1-((2S,3R,4R)-2,3-dimethyl-4-((5-methylpyrazin-2-yl)amino)-6-(tetrahydro-2H-pyran-4-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28 mg	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 72h;Inert atmosphere;	a reaction vessel 4-bromo-N-methylbenzamide (53.1 mg, 0.248 mmol), rac-1-((2S,3R,4R)-4- amino-2,3-dimethyl-6-(tetrahyd ro-2H-pyran-4-yl)-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for apreparation see Intermediate 152, 37.5 mg, 0.124 mmol), sodium tert-butoxide (35.8 mg, 0.372 mmol), in 1,4-Dioxane (5 mL) were added. The solution was treated with Pd2(dba)3 (17.03 mg, 0.019 mmol) and DavePhos (9.76 mg, 0.025 mmol) and left to stir at 100 C for 2 h under N2. The reaction mixture was allowed to cool to rt and then filtered through celite and the celite washed with ethyl acetate. The combined filtrates were concentrated in vacuo to a crude orange/brown gum. This gumwas purified by MDAP (Formic) to give asolid. This solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated to give the product (17 mg, 0.039 mmol, 31.5%) as an off-white solid. LCMS (2 mm Formic): Rt = 0.83 mi [MH] = 436.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 323

21
[ 59303-10-5 ]
rac-tert-butyl 4-((2S,3R,4R)-1-acetyl-4-amino-2-ethyl-3-methyl-1,2,3,4-tetrahydroquinolin-6-yl)piperazine-1-carboxylate [ No CAS ]
rac-tert-butyl 4-((2S,3R,4R)-1-acetyl-2-ethyl-3-methyl-4-((5-methylpyrazin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.5%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere; Microwave irradiation;	A 0.5-2 mL microwave vial was evacuated and back filled with N2. rac-tert-Butyl 4-((2S,3R,4R)-1- acetyl-4-am ino-2-ethyl-3-methyl- I ,2,3,4-tetrahydroq uinolin-6-yl)piperazine- I -carboxylate (for a preparation see Intermediate 172, 46 mg, 0.110 mmol) in I ,4-dioxane (1.5 mL) was then added. To this was added <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (28.4 mg, 0.221 mmol), sodium tert-butoxide (21.23 mg,0.221 mmol) and DavePhos (8.69 mg, 0.022 mmol) and the resultant suspension then had N2 bubbled through it for -5 mi Pd2(dba)3 (20.22 mg, 0.022 mmol) was added and N2 was bubbled through the reaction mixture for a further -5 mm. The reaction was then heated to 100 C for 30 mm in a microwave. The reaction was then reheated to 100 C in a microwave for 30 mm. The reaction mixture was diluted with EtOAc and filtered though celite (2.5 g). The celite was washed with furtherEtOAc (2x10 mL) and the resultant solution concentrated in vacuo. This was taken up inMeOH/DMSO (1:1, 0.9 mL) and purified by MDAP (Formic). The appropriate fraction was collectedand concentrated in vacuo to afford an orange glass (21 .6 mg, 0.042 mmol, 38.5%).LCMS (2 mm Formic): Rt = 1.07 mi [MH] = 509.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 136; 137

22
[ 59303-10-5 ]
(S)-tert-butyl 4-((rac-2S,3R,4R)-1-acetyl-4-amino-2-cyclopropyl-3-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-2-methylpiperazine-1-carboxylate [ No CAS ]
(S)-tert-butyl 4-((rac-2S,3R,4R)-1-acetyl-2-cyclopropyl-3-methyl-4-((5-methylpyrazin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)-2-methylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.5%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 120℃; for 0.666667h;Microwave irradiation;	To a microwave vial was added (S)-tert-butyl 4-((rac-2S,3R,4R)-1-acetyl-4-amino-2-cyclopropyl-3- methyl-I ,2,3,4-tetrahydroq uinolin-6-yl)-2-methylpiperazine- I -carboxylate (for a preparation see Intermediate 179, 37.7 mg, 0.085 mmol) in 1,4-dioxane (2.5 mL). To this was added <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (21.90 mg, 0.170 mmol), Pd2(dba)3 (15.60 mg, 0.017 mmol), sodium tert-butoxide (24.56 mg, 0.256 mmol) and DavePhos (13.41 mg, 0.034 mmol). The vessel was sealed and heated on a microwave heater at 120 C for 40 mm. The reaction mixture was filtered over a 2.5 g celite cartridge, washed through with ethyl acetate and concentrated in vacuo. The residue was dissolved in MeOH:DMSO (1:1, 1 mL) and purified by MDAP (Formic). The solvent was evaporated in vacuo to give the required product (5.7 mg, 12.5%). LCMS No data.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 141; 142

23
[ 59303-10-5 ]
rac-(2S,3R,4R)-1-acetyl-4-amino-2-cyclopropyl-N,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxamide [ No CAS ]
rac-(2S,3R,4R)-1-acetyl-2-cyclopropyl-N,3-dimethyl-4-((5-methylpyrazin-2-yl)amino)-1,2,3,4-tetrahydroquinoline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.5%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere;	To a reaction vessel <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (81 mg, 0.630 mmol), rac-(2S,3R,4R)-1-acetyl-4- amino-2-cyclopropyl-N ,3-dimethyl- 1,2 ,3,4-tetrahydroqu inoline-6-carboxamide (for preparation see Intermediate 200, 80 mg, 0.265 mmol), sodium tert-butoxide (77 mg, 0.796 mmol), in I ,4-dioxane (5 mL) were added. The solution was treated with Pd2(dba)3 (36.5 mg, 0.040 mmol) and DavePhos (20.89 mg, 0.053 mmol) and left to stir at 100 C for 2 h under N2. The reaction mixture was allowedto cool to rt and then filtered through celite and the celite washed with ethyl acetate. The combined filtrates were concentrated in vacuo to give a crude orange/brown gum. This gum was purified by MDAP (Formic) to give a solid, this solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated to give the product (59 mg, 0.150 mmol, 56.5%) as a beige solid.LCMS (2 mm Formic): Rt = 0.70 mi [MH] = 394.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 355

24
[ 59303-10-5 ]
tert-butyl 4-((2S,3R,4R)-1-acetyl-4-amino-2,3-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)piperazine-1-carboxylate [ No CAS ]
tert-butyl 4-((2S,3R,4R)-1-acetyl-2,3-dimethyl-4-((5-methylpyrazin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10 mg	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 0.75h;Microwave irradiation;	A microwave vial was charged with tert-butyl 4-((2S ,3R,4R)- I -acetyl-4-amino-2,3-dimethyl- 1,2,3,4-tetrahydroquinolin-6-yl)piperazine- I -carboxylate (for a preparation see Intermediate 213, 69 mg,0.151 mmol) in 1,4-dioxane (2 mL) followed by <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (37 mg, 0.288 mmol),then sodium tert-butoxide (27 mg, 0.281 mmol), DavePhos (12 mg, 0.030 mmol), and Pd2(dba)3 (26 mg, 0.028 mmol). The reaction mixture was heated to 100 C for 45 mm using a microwave reactor, then diluted with EtOAc and filtered through a pad of celite. The celite pad was washed with EtOAc (10 mL) and the filtrate concentrated under reduced pressure. The residue was purified by MDAP(Formic). The desired fractions were combined and evaporated in vacuo to afford the desired product

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 155; 156

25
[ 59303-10-5 ]
rac-1-((2S,3R,4R)-4-amino-2-ethyl-6-fluoro-3-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]
rac-1-((2S,3R,4R)-2-ethyl-6-fluoro-3-methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.6%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 18h;	The rac- I -((2S,3R,4R)-4-amino-2-ethyl-6-fluoro-3-methyl-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for a preparation see Intermedaite 40, 100 mg, 0.400 mmol), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (77mg, 0.599mmo1), Pd2(dba)3 (54.9 mg, 0.060 mmol), sodium tert-butoxide (115 mg, 1.199 mmol) andDavePhos (15.72 mg, 0.040 mmol) were suspended I ,4-dioxane (10 mL) and allowed to stir at 100C for 18 h. The reaction was allowed to cool to rt and were filtered through celite and concentratedto a gum. This gum was purified using a MDAP (Formic) to give a solid, this solid was eluted througha NH2 SPE (5 g) with MeOH, the eluent was concentrated and dried to give the product (50 mg,0.146 mmol, 36.6%) as an off-white solid. LCMS (2 mm Formic): Rt = 0.89 mi [MH] = 343.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 315

26
[ 59303-10-5 ]
rac 1-((2S,3R,4R)-4-amino-2,3-dimethyl-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]
1-((2S,3R,4R)-2,3-dimethyl-4-((5-methylpyrazin-2-yl)amino)-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9 mg	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 0.75h;Microwave irradiation;	A microwave vial was charged with I -((2S,3R,4R)-4-am ino-2,3-dimethyl-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone (for a preparation see Intermediate 211, 125 mg, 72% purity,0.297 mmol, -25% ee) in 1,4-dioxane (2 mL) followed by <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (76 mg, 0.593mmol), then sodium tert-butoxide (57 mg, 0.593 mmol), DavePhos (24 mg, 0.061 mmol), andPd2(dba)3 (54 mg, 0.059 mmol). The reaction mixture was heated to 100 C for 45 mm using amicrowave.reactor, then diluted with EtOAc and filtered through a pad of celite. The celite pad was washed with EtOAc (10 mL) and the filtrate concentrated under reduced pressure. The residue was purified by MDAP (Formic). The desired fractions were combined and evaporated in vacuo and the residue dissolved in methanol then passed through an amino-propyl SPE column which was washed with further methanol. The methanol washes were combined then concentrated in vacuo to to affordthe desired product as a white solid (9 mg, -25% ee). LCMS (2 mm Formic): Rt = 0.75 mi [MH] = 396.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 334; 335

27
[ 59303-10-5 ]
rac-1-((2S,3R,4R)-4-amino-2-ethyl-3-methyl-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]
rac-1-((2S,3R,4R)-2-ethyl-3-methyl-4-((5-methylpyrazin-2-yl)amino)-6-morpholino-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14 mg	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 120℃; for 0.5h;Microwave irradiation;	To a solution of rac- I -((2S,3R,4R)-4-amino-2-ethyl-3-methyl-6-morpholino-3,4-dihydroqu inolin1(2H)-yl)ethanone (for a preparation see Intermediate 73, 50 mg, 0.158 mmol) in 1,4-dioxane (1.5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (28.8 mg, 0.032 mmol), Davephos (12.40mg, 0.032 mmol), sodium tert-butoxide (30.3 mg, 0.315 mmol) and <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (40.5 mg, 0.315 mmol). The reaction mixture was heated under microwave conditions, using initial normal absorption setting, to 120 C for 30 mm. The sample was diluted with ethyl acetate (5 mL) and loaded onto a celite cartridge (2.5 g). The cartridge was washed with further ethyl acetate (2x10 mL), and the combined fractions dried under a stream of nitrogen. The sample was dissolved in DMSO(2x1 mL) and purified by MDAP (HpH). The solvent was blown down under a stream of nitrogen to give the required product (14 mg) as a yellow gum. LCMS (2 mm HpH): Rt = 0.87 mi [MH] = 410.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 336

28
[ 59303-10-5 ]
rac-1-((2S,3R,4R)-4-amino-2-cyclopropyl-6-(3,6-dihydro-2H-pyran-4-yl)-3-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]
rac-1-((2S,3R,4R)-2-cyclopropyl-6-(3,6-dihydro-2H-pyran-4-yl)-3-methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-1(2H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.9%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In 1,4-dioxane; at 100℃; for 3h;Inert atmosphere;	The <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (0.053 mL, 0.613 mmol), rac-l -((2S,3R,4R)-4-amino-2-cyclopropyl-6-(3,6-dihydro-2H-pyran-4-yl)-3-methyl-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for a preparation seeIntermediate 78, 100 mg, 0.306 mmol), Pd2(dba)3 (42.1 mg, 0.046 mmol), sodium tert-butoxide (88mg, 0.919 mmol) and DavePhos (12.06 mg, 0.031 mmol) were suspended in 1,4-dioxane (10 mL)and allowed to stir at 100 C for 3 h. The reaction was allowed to cool and was partitioned between water and EtOAc, the organic layer was washed with brine, dried using a hydrophobic frit and concentrated to a gum. This gum was purified by column chromatography on silica gel eluting with 0- 50% EtOAc:cyclohexane and then 0-10% MeOH:DCM, to give a crude gum. This gum was furtherpurified using a MDAP (Formic) to give a white solid, this solid was eluted through a NH2 SPE (2 g) with MeOH the eluent was concentrated and dried to give the product (46 mg, 0.110 mmol, 35.9%) as an off-white solid. LCMS (2 mm Formic): Rt = 0.93 mi [MH] = 419.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 325; 326

29
[ 59303-10-5 ]
(-)-R-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate [ No CAS ]
(R)-tert-butyl 3,3-difluoro-4-(((5-methylpyrazin-2-yl)amino)methyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃;Inert atmosphere;	To a solution of R-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate (188 mg, 0.75mmol) in dioxane (3 mL) were added <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (100 mg, 0.78 mmol),Pd2(dba)3CHCI3(21 mg, 0.02 mmol ), Xantphos (23 mg, 0.04 mmol) and Cs2CO3 (329 mg, 1.0 mmol). The mixture was heated to 90C under N2. After stirring overnight, the reaction solution was treated with ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography over silica gel (ethyl acetate/hexane = 1/1) to afford the title compound as a pale-yellow powder (115 mg, 45%). MS (ESI) calcd for C16H24F2N402: 342.2 ; found: 343.4[M+H]. 1H NMR (400 MHz, CDCI3) 6 7.86 (s, 1H), 7.83 (s, 1H), 4.63-4.53 (m, 1H), 4.48-4.04 (m, 2H), 3.73-3.67 (m, 1H), 3.52-3.45 (m, 1H), 3.00-2.89 (m, 1H),2.79-2.70 (m, 1H), 2.38 (s, 3H), 2.28-2.15 (m, 1H), 1.85-1.80 (m, 1H), 1.47 (s, 9H).

Reference： [1]Patent: WO2016/196513,2016,A1 .Location in patent: Paragraph 0245

30
[ 59303-10-5 ]
[ 35344-95-7 ]
1-(5-methylpyrazin-2-yl)-1H-pyrazole-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.10%	With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 6h;	To a solution of 2-chloro-5-methylpyrazine (2.00 g, 15.56 mmol) in DMF (50 mL) was added <strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (2.24 g, 23.34 mmol) followed by Cs2CO3 (10.14 g, 31.10 mmol) and the resulting reaction mixture was heated at 100°C for 6 h. The reaction mixture was cooled to ambient temperature, concentrated to dryness under reduced pressure, diluted with water (50 mL) and extracted with ethyl acetate (2 x 75 mL). The combined organic layers was washed with brine (30 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Redisep - 80 g, 0-100percent EtOAc/n-hexane) to obtain Intermediate 125 (1.10 g, 37.10percent) as a pale yellow solid.1H NMR (300 MHz, DMSO-d6) G ppm 2.58 (s, 3 H), 8.36 (s, 1 H), 8.54 (s, 1 H), 9.14 (s, 1 H), 9.31 (s, 1 H), 9.98 (s, 1 H). LCMS (Method- D): retention time 1.25 min, [M+H] 189.2.

Reference： [1]Patent: WO2018/222795,2018,A1 .Location in patent: Page/Page column 256; 257

31
[ 59303-10-5 ]
[ 143557-91-9 ]
tert-butyl (1R,3r,5S)-3-(5-methylpyrazin-2-yl)oxy-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium tert-butylate; In tetrahydrofuran; for 16h;Reflux;	General procedure: . Following GP2, t-BuOK (0.1 g, 1 eq., 0.88 mmol) was added to a solution of tert-butyl (1R,3r,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (0.2 g, 1 eq., 0.88 mmol), and <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (0.11 g, 1 eq., 0.88 mmol) in dry THF (7 mL). The reaction mixture was refluxed for 16 h. Then, the mixture was quenched with water (15 mL) and extracted with DCM (210 mL). The organic extracts were washed with brine (15 mL), dried over Na2SO4 and concentrated in vacuo to furnish the crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (0 to 80%) to give the pure title compound as colourless oil (0.07 g, 25%). UPLC-MS (method A): Rt. 2.58 min (TIC); ionization ES+320 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 8.17 (d, J=1.3 Hz, 1H), 8.06 (s, 1H), 5.26 (t, J=5.0 Hz, 1H), 4.18-4.03 (m, 2H), 2.39 (s, 3H), 2.17-1.97 (m, 4H), 1.96-1.77 (m, 4H), 1.42 (s, 9H).

Reference： [1]Patent: US2019/135778,2019,A1 .Location in patent: Paragraph 0168-0169; 0112-0113

32
[ 59303-10-5 ]
[ 109384-19-2 ]
C₁₅H₂₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		NaH (60% in mineral oil, 103 mg, 2.57 mmol) was added to a stirred solution of l-Boc- 4-hydroxypiperidine (CAS: 109384-19-2; 470 mg, 2.33 mmol) in DMF (10 mL) at 0 C under N2 atmosphere. The mixture was stirred at room temperature for 1 h. 2-Chloro-5- methylpyrazine (CAS: 59303-10-5; 300 mg, 2.33 mmol) was added to the mixture under N2 atmosphere and the reaction mixture was stirred at 50 C for 16 h. A solution of 1- Boc-4-hydroxypiperidine (CAS: 109384-19-2) in DMF which was stirred for 1 h at room temperature was added, and the reaction mixture was stirred at 80 C for another 16 h. The mixture was diluted with water and extracted with DCM. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 80:20). The desired fractions were collected and concentrated in vacuo to afford intermediate 151 (320 mg, 47%) as a white solid.

Reference： [1]Patent: WO2019/243530,2019,A1 .Location in patent: Page/Page column 67

33
[ 59303-10-5 ]
[ 109384-19-2 ]
C₁₀H₁₅N₃O [ No CAS ]

Reference： [1]Patent: WO2019/243530,2019,A1

34
[ 59303-10-5 ]
[ 147081-49-0 ]
(R)-tert-butyl 3-((5-methylpyrazin-2-yl)amino)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 80℃; for 3h;Inert atmosphere;	A mixture of <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (300 mg, 1.6 mmol), (R)-tert-butyl 3-aminopyrrolidine-l- carboxylate (206 mg, 1.6 mmol), BINAP (199 mg, 0.3 mmol), Pd2(dba)3 (73 mg, 0.08 mmol) and t- BuONa (307 mg, 3.2 mmol) in toluene (10 mL) was stirred at 80C under N2 for 3 hours. The mixture was cooled to RT and concentrated. The residue was purified by reverse phase chromatography to afford (R)-tert-butyl 3-((5-methylpyrazin-2-yl)amino)pyrrolidine-l-carboxylate (240 mg, 54%) as yellow oil. [M+H] Calc?d for Ci4H22N402, 279.1; Found, 279.1.

Reference： [1]Patent: WO2020/6497,2020,A1 .Location in patent: Paragraph 00376

35
[ 59303-10-5 ]
[ 5350-57-2 ]
2‐[2‐(diphenylmethylidene)hydrazin‐1‐yl]‐5‐methylpyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate; In toluene; at 90℃; for 5h;Inert atmosphere; Sealed tube;	A pressure tube was charged with benzophenone hydrazine (1.07 g, 5.4 mmol), <strong>[59303-10-5]2-chloro-5-methylpyrazine</strong> (500 mg, 3.9 mmol), sodium tert-butoxide (523 mg, 5.4 mmol), JohnPhos (34.8 mg, 0.12 mmol), Pd2(dba)3 (35.6 mg, 0.04 mmol) and degassed toluene (6 mL). The suspension was degassed further with N2 and sealed. The reaction was heated at 90 oC for 5 h. The reaction was allowed to cool to room temperature and was quenched with water (20 mL). The reaction was neutralized with 1M HCl(aq). The mixture was extracted with EtOAc (3 x 20 mL). The combined organic extracts were washed with brine (40 mL), dried (Na2SO4), filtered and concentrated. The crude product was purified by Biotage Isolera chromatography (silica gel, eluting with 0-16% EtOAc in heptane) to give 950 mg (85% yield) of the title compound as a white solid.1H NMR (500 MHz, CDCl3) d 8.81 (d, J = 1.1 Hz, 1H), 8.02 (s, 1H), 7.85 (s, 1H), 7.62- 7.55 (m, 4H), 7.54- 7.50 (m, 1H), 7.38- 7.33 (m, 4H), 7.33- 7.30 (m, 1H), 2.46 (s, 3H). LCMS (Analytical Method D) Rt= 1.30 min, MS (ESIpos): m/z= 288.90 [M+H]+.

Reference： [1]Patent: WO2020/97609,2020,A1 .Location in patent: Page/Page column 184-185

36
[ 59303-10-5 ]
2‐hydrazinyl‐5‐methylpyrazine dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2020/97609,2020,A1

37
[ 59303-10-5 ]
6‐methyl‐2H,3H‐[1,2,4]triazolo[4,3‐a]pyrazin‐3‐one [ No CAS ]

Reference： [1]Patent: WO2020/97609,2020,A1

38
[ 109-08-0 ]
[ 38557-71-0 ]
[ 59303-10-5 ]
[ 95-58-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; triethylamine; In 1,2-dichloro-ethane; at 45 - 60℃; under 150.015 - 225.023 Torr; for 4.5h;Large scale;	100L enamel reaction kettle, equipped with material dropping pipe (connected with metering pump), equipped with chlorine gas introduction pipe (connected with chlorine gas automatic control system), automatic pressure control system, temperature detection chain control system. Add 96kg of solvent dichloroethane and 1kg of triethylamine to the reaction kettle and start stirring, then pass chlorine gas, and set the pressure in the kettle to be automatically controlled at 0.02-0.03MPa for 20-30 minutes. Then start feeding with a metering pump at a rate of 5kg/h (according to 10kg of methylpyrazine mixed with 10kg of dichloroethane to be used evenly), the reaction exotherm is obvious, the reaction temperature is controlled at 45 ~ 60 C , the temperature is higher than 60C. The feeding system is automatically cut off at (if necessary, the water flow can be manually controlled to lower the temperature), the beating is completed in about 4 hours, and then the reaction is continued for 30 minutes at a pressure of 0.02 ~ 0.03MPa. Then lower the temperature to 30-40C, introduce the residual chlorine gas in the reaction kettle into the lye spray absorption tower to absorb, the remaining reaction liquid in the kettle is pressed into the dichloroethane turnover tank with nitrogen through the pipeline filter (containing chlorine gas for recycling), the reaction kettle The remaining chloropyrazine hydrochloride solid is dissolved in 30Kg of water first, and then neutralized with 30% alkaline solution to pH 6-7, and then separated into layers to obtain crude chloropyrazine, about 12Kg, content about 92 % Is directly used for the next reaction.

Reference： [1]Patent: CN110963974,2020,A .Location in patent: Paragraph 0027-0028; 0031-0032

39
[ 59303-10-5 ]
[ 68716-48-3 ]
C₁₁H₉N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.87%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane at 90℃; for 6h; Inert atmosphere;	27 Synthesis of compound 27.3. Argon was purged for 15 min through a stirred mixture of compounds 27.1 (3.0g, 12.00mmol, 1.0eq), 27.2 (1.9g, 15.6mmol, 1.3eq), and tripotassium phosphate (6.3g, 30.0mmol, 2.5eq) in 1,4-dioxane (60mL). [1,1'- bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.877mg, 1.2mmol, 0.1eq) was added to it and further purging done for 10 min. Reaction was stirred at 90°C for 6h. After completion of reaction, reaction mixture was poured over water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to obtain 27.3. (1.5g, Yield: 57.87%). MS (ES): m/z 216.07 [M+H]+.

Reference： [1]Current Patent Assignee: NIMBUS THERAPEUTICS INC; SCHROEDINGER LLC - WO2020/112937, 2020, A1 Location in patent: Paragraph 00505-00506

40
[ 59303-10-5 ]
[ 1609393-90-9 ]
2-methoxy-3-(5-methylpyrazin-2-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In 1,4-dioxane; water at 105℃; for 20h; Sealed tube; Inert atmosphere;

Reference： [1]Liu, Chunjian; Lin, James; Langevine, Charles; Smith, Daniel; Li, Jianqing; Tokarski, John S.; Khan, Javed; Ruzanov, Max; Strnad, Joann; Zupa-Fernandez, Adriana; Cheng, Lihong; Gillooly, Kathleen M.; Shuster, David; Zhang, Yifan; Thankappan, Anil; McIntyre, Kim W.; Chaudhry, Charu; Elzinga, Paul A.; Chiney, Manoj; Chimalakonda, Anjaneya; Lombardo, Louis J.; Macor, John E.; Carter, Percy H.; Burke, James R.; Weinstein, David S. [Journal of Medicinal Chemistry, 2021, vol. 64, # 1, p. 677 - 694]

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[ CAS No. 59303-10-5 ] {[proInfo.proName]}

Quality Control of [ 59303-10-5 ]

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[ 59303-10-5 ] Synthesis Path-Upstream 1~6

[ 59303-10-5 ] Synthesis Path-Downstream 1~40

Related Functional Groups of [ 59303-10-5 ]

Chlorides

Related Parent Nucleus of [ 59303-10-5 ]

Pyrazines

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[ 59303-10-5 ]

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[ 59303-10-5 ]