[ CAS No. 98139-15-2 ] {[proInfo.proName]}

Name: 98139-15-2|4-Aminopicolinonitrile|97%
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Quality Control of [ 98139-15-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 98139-15-2 ]

Product Details of [ 98139-15-2 ]

CAS No. :	98139-15-2	MDL No. :	MFCD07374351
Formula :	C₆H₅N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GMKRESMCPMIWGU-UHFFFAOYSA-N
M.W :	119.12	Pubchem ID :	23131454
Synonyms :

Calculated chemistry of [ 98139-15-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.36
TPSA :	62.7 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.85
Log Po/w (XLOGP3) :	0.22
Log Po/w (WLOGP) :	0.54
Log Po/w (MLOGP) :	-0.84
Log Po/w (SILICOS-IT) :	0.62
Consensus Log Po/w :	0.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.21
Solubility :	7.34 mg/ml ; 0.0616 mol/l
Class :	Very soluble
Log S (Ali) :	-1.1
Solubility :	9.55 mg/ml ; 0.0801 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.7
Solubility :	2.37 mg/ml ; 0.0199 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 98139-15-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 98139-15-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 98139-15-2 ]
Downstream synthetic route of [ 98139-15-2 ]

[ 98139-15-2 ] Synthesis Path-Upstream 1~2

1
[ 557-21-1 ]
[ 14432-12-3 ]
[ 98139-15-2 ]

Yield	Reaction Conditions	Operation in experiment
20%	at 145℃; for 20 h;	A mixture of 2-chloro-pyridin-4-ylamine (0.642 g, 5 mmol), Zn (CN) 2 (0.323 g, 2.75 mmol) and Pd (PPh3) 4 (0.288 g, 0.025 mmol) in 5 mL of DMF was heated at 145 C for 20 hours. After the reaction mixture cooled to room temperature, it was partitioned between ethyl acetate and H2O. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried (MGS04), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9: 1 HEXANES/ETHYL acetate to provide 0.29 g (20percent) of the desired product. MS (DCI) m/e 120 (M+H) + ; IH NMR (300 MHz, DMSO-D6) 8 8.08 (d, J=5.76 Hz, 1H), 6.94 (d, J=2.34 Hz, 1H), 6.68 (dd, J=5. 76,2. 37 Hz, 1H), 6.59 (s, 2H).

Reference： [1] Patent: WO2004/76424, 2004, A1, . Location in patent: Page 131

2
[ 19235-89-3 ]
[ 98139-15-2 ]

Reference： [1] Patent: WO2017/181177, 2017, A1,

[ 98139-15-2 ] Synthesis Path-Downstream 1~20

2
[ 557-21-1 ]
[ 14432-12-3 ]
[ 98139-15-2 ]

Yield	Reaction Conditions	Operation in experiment
20%	tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 145℃; for 20h;	A mixture of 2-chloro-pyridin-4-ylamine (0.642 g, 5 mmol), Zn (CN) 2 (0.323 g, 2.75 mmol) and Pd (PPh3) 4 (0.288 g, 0.025 mmol) in 5 mL of DMF was heated at 145 C for 20 hours. After the reaction mixture cooled to room temperature, it was partitioned between ethyl acetate and H2O. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried (MGS04), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9: 1 HEXANES/ETHYL acetate to provide 0.29 g (20%) of the desired product. MS (DCI) m/e 120 (M+H) + ; IH NMR (300 MHz, DMSO-D6) 8 8.08 (d, J=5.76 Hz, 1H), 6.94 (d, J=2.34 Hz, 1H), 6.68 (dd, J=5. 76,2. 37 Hz, 1H), 6.59 (s, 2H).

Reference： [1]Patent: WO2004/76424,2004,A1 .Location in patent: Page 131

3
[ 98139-15-2 ]
[ 530-62-1 ]
C₇H₃N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 20℃; for 1.5h;Inert atmosphere;	Step One & Two. N-(2-Cyanopyridin-4-yl)-6-hydroxy-2,4-dioxo- 1,2,3,4- tetrahydropyrimidine-5-carboxamide (H3)L_TO a solution of compound C2 (0.713 g, 4.40 mmol) in anhydrous DMSO (2 mL) was added compound HI (0.476 g, 4.00 mmol) at ambient temperature under nitrogen. The reaction mixture was then stirred for 1.5 h to provide a solution of compound H2 in DMSO which was used directly in the subsequent step.

Reference： [1]Patent: WO2015/123003,2015,A1 .Location in patent: Paragraph 00169

4
[ 98139-15-2 ]
N-(2-cyanopyridin-4-yl)-6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/123003,2015,A1

5
methyl 4-(tert-butylsulfamoyl)-3-chloro-1-methyl-pyrrole-2-carboxylate [ No CAS ]
[ 98139-15-2 ]
4-(tert-butylsulfamoyl)-3-chloro-N-(2-cyanopyridin-4-yl)-1-methyl-1H-pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10 mg	With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 20℃; for 3h;Cooling with ice;	Methyl 4-(tert-butylsulfamoyl)-3-chloro-l -methyl -pyrrole-2-carboxylate (50 mg, 0.16 mmol) and <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (0.021 g, 0.18 mmol) were dissolved in THF (5 mL) and cooled in an ice bath. To this was added dropwise lithium bis(trimethylsilyl)amide in toluene (0.32 mL, 1 M, 0.32 mmol) over a period of 5 minutes. The resulting mixture was allowed to reach room temperature and was stirred for 3 hours. The resulting mixture was quenched using ammonium chloride (10 mL / aq. sat.). This was extracted using ethylacetate (3 X 20 mL). The combined extracts were washed with brine (20 mL), dried on Na2S04, filtered and concentrated in vacuo. The obtained crude was purified by silica gel column chromatography using gradient elution from heptane to iPrOH. (100:0 to 70:30). The desired fractions were concentrated in vacuo and dried in a vacuum oven at 55 C for 24 hours yielding compound 6 (10 mg) as a bright white powder. Method B; Rt: 0.91 min. m/z : 394.0 (M-H)~ Exact mass: 395.1. 1H NMR (0198) (400 MHz, DMSO-d6) delta ppm 1.18 (s, 9 H), 3.79 (s, 3 H), 7.38 (s, 1 H), 7.65 (s, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.20 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.5 Hz, 1 H), 10.97 (br. s., 1 H).

Reference： [1]Patent: WO2015/118057,2015,A1 .Location in patent: Page/Page column 27; 28

6
ethyl 3-fluoro-1-methyl-4-[[(1R)-2,2,2-trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylate [ No CAS ]
[ 98139-15-2 ]
N-(2-cyanopyridin-4-yl)-3-fluoro-1-methyl-4-[(1R)-2,2,2-trifluoro-1-methylethyl]sulfamoyl}-1H-pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47 mg	With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 0 - 20℃;Inert atmosphere;	To ethyl 3-fluoro-l -methyl -4-[[(lR)-2,2,2-trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2- carboxylate (128 mg, 0.37 mmol)and <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (57.2 mg, 0.48 mmol) dissolved in dry THF (20 mL) at 0C under nitrogen atmosphere, lithium (0240) bis(trimethylsilyl)amide in toluene (1.5 mL, 1 M, 1.478 mmol) was added. The mixture was stirred 1 hour at 0C and further overnight at room temperature. The reaction mixture was quenched with NH4C1 solution (30 mL) and extracted with EtOAc (50 mL), diluted with brine (50 mL) and extracted again with EtOAc (50 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated. The residue (dissolved in 1 mL DMF) was purified by column chromatography on silica gel using a 120g Reveleris cartridge with a gradient from 10 till 100% EtOAc in heptane. The product fractions were concentrated and the solid residue was crystallised from warm methanol (20 mL) upon addition of water. The light yellow crystals were filtered off and dried in vacuo at 50C overnight, resulting in compound 18 (47 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.18 (d, J=6.8 Hz, 3 H), 3.82 (s, 3 H), 3.93 - 4.04 (m, 1 H), 7.62 (d, J=4.4 Hz, 1 H), 7.91 (dd, J=5.7, 2.2 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.60 - 8.69 (m, 2 H), 10.72 (s, 1 H). Method D: Rt: 1.70 min. m/z: 418.0 (M-H)~ Exact mass: 419.1.

Reference： [1]Patent: WO2015/118057,2015,A1 .Location in patent: Page/Page column 34

7
ethyl 3-chloro-1,5-dimethyl-4-[[(1R)-2,2,2-trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylate [ No CAS ]
[ 98139-15-2 ]
3-chloro-N-(2-cyano-4-pyridyl)-1,5-dimethyl-4-[[(1R)-2,2,2-trifluoro-1-methylethyl]sulfamoyl]pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29 mg	With lithium hexamethyldisilazane; In tetrahydrofuran; at 20℃;	Ethyl 1,5 -dimethyl- lH-pyrrole-2-carboxylate (2.5g, 15 mmol) was added drop wise to chlorosulfonic acid (10 mL, 150 mmol) at 0C under nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was slowly added to ice-water (200 mL), followed by extraction with DCM (3 x 100 mL). The combined organic extracts were dried (Na2S04) and concentrated to give a light purple powder which decomposed over time to a dark sticky powder. This was dissolved in SOCl2 (8 mL, 110 mmol) and stirred 1 hour at 80C. The reaction mixture was concentrated and the residue was subjected to column chromatography on a Reveleris 120g cartridge using a gradient from 10 till 50 % EtOAc in heptane. The product fractions were concentrated to dryness yielding ethyl 4-chlorosulfonyl-l,5-dimethyl-pyrrole-2-carboxylate (600 mg) as white powder. Ethyl 4- chlorosulfonyl-l,5-dimethyl-pyrrole-2-carboxylate (600 mg, 2.26 mmol) was dissolved in ACN (4 mL) and dried on molecular sieves and NaHC03 (1.39 g, 16.5 mmol) was added. (R)-l,l,l- trifluoro-2-propylamine (766 mg, 6.77 mmol) was dissolved in ACN (1 mL) and dried on molecular sieves. The two suspensions were combined and heated at 80C for 4 hours. The reaction mixture was filtered and the filter cake was washed with acetonitrile. The combined filtrates were evaporated to dryness and the residue was purified using silica gel column chromatography to afford ethyl l,5-dimethyl-4-[[(lR)-2,2,2-trifluoro-l-methyl- ethyl]sulfamoyl]pyrrole-2-carboxylate (600 mg) as co lories sticky powder. (0292) Ethyl l,5-dimethyl-4-[[(lR)-2,2,2-trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylate (400 mg, 1.17 mmol) was dissolved in HO Ac (10 mL) and NCS (156 mg, 1.17 mmol) was added. The reaction mixture was heated at 40C over weekend. The reaction mixture was evaporated to dryness and the residue was purified using silica gel column chromatography (0293) (EtOAc in heptane from 0 to 100% to afford crude product which was purified again using silica gel column chromatography using methanol in DCM from 0.1 to 0.5 % to afford ethyl 3-chloro- l,5-dimethyl-4-[[(lR)-2,2,2-trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylate (177 mg). Method D: Rt: 1.89 min. m/z: 375 (M-H)~ Exact mass: 376.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.12 (d, J=7.0 Hz, 3 H), 1.30 (t, J=7.2 Hz, 3 H), 2.48 (s, 3 H), 3.75 (s, 3 H), 3.82 - 3.94 (m, 1 H), 4.29 (q, J=7.0 Hz, 2 H), 8.42 (br. s., 1 H). Ethyl 3-chloro-l,5-dimethyl-4-[[(lR)-2,2,2-trifluoro-l-methyl-ethyl]sulfamoyl]pyrrole-2- carboxylate (88 mg , 0.23 mmol) and <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (33.4 mg, 0.28 mmol) were dissolved in THF (10 mL). Lithium bis(trimethylsilyl)amide (0.7 mL, 1 M, 0.7 mmol) was added drop wise and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with sat. NH4C1 (5 mL). The organic layer was removed and the aqueous layer extracted with DCM (2 X 5 mL). The combined organic layers were evaporated to dryness and the residue was purified on silica (EtOAc in heptane from 0 to 100%) to afford a white powder. A second purification was performed via Prep HPLC (Stationary phase: RP XBridge Prep C18 OmicronBeta-10muiotaeta,30chi150iotaetaiotaeta, Mobile phase: 0.25% NH4HCO3 solution in water, MeOH) yielding compound 32 (29 mg) as a white powder. Method B: Rt: 0.93 min. m/z: 448 (M-H)~ Exact mass: 449.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.17 (d, J=6.8 Hz, 3 H), 2.48 - 2.52 (m, 3 H), 3.65 (s, 3 H), 3.94 (spt, J=7.2 Hz, 1 H), 7.91 (dd, J=5.6, 2.1 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.45 (br. s., 1 H), 8.65 (d, J=5.7 Hz, 1 H), 11.05 (br. s., 1 H).

Reference： [1]Patent: WO2015/118057,2015,A1 .Location in patent: Page/Page column 42; 43

8
ethyl 3-fluoro-1-methyl-4-[[1-(trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate [ No CAS ]
[ 98139-15-2 ]
N-(2-cyano-4-pyridyl)-3-fluoro-1-methyl-4-[[1-(trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51 mg	With lithium hexamethyldisilazane; In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere;	Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1500 mg, 5.56 mmol) was dissolved in dry pyridine (26.25 mL, 325.2 mmol). l-(trifluoromethyl)cyclopropan-l -amine (1392 mg, 11.1 mmol) was added and the mixture was stirred at 70C for 6 hours. The mixture was concentrated in vacuo. The obtained residue was purified by silica gel column (0877) chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (1.21 g) as a beige powder. Ethyl 3-fluoro-l-methyl-4-[[l- (0878) (trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.31 mmol) and (0879) <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (40.05 mg, 0.34 mmol) were dissolved in THF (3 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (0.76 mL, 1 M, 0.76 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC on (RP SunFire Prep CI 8 OmicronBeta-10muetaiota,30chi150etaiotaetaiota). Mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours resulting in compound 192 (51 mg) as a white powder. Method B: Rt: 0.90 min. m/z: 430.1 (M-H)" Exact mass: 431.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.14 - 1.30 (m, 4 H), 3.75 - 3.89 (m, 3 H), 7.57 (d, J=4.6 Hz, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.21 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.7 Hz, 1 H), 9.15 (br. s., 1 H), 10.67 (br. s., 1 H).

Reference： [1]Patent: WO2015/118057,2015,A1 .Location in patent: Page/Page column 124; 125

9
ethyl 3-fluoro-1-methyl-4-[(2,2,2-trifluoro-1,1-dimethylethyl)sulfamoyl]pyrrole-2-carboxylate [ No CAS ]
[ 98139-15-2 ]
N-(2-cyano-4-pyridyl)-3-fluoro-1-methyl-4-[(2,2,2-trifluoro-1,1-dimethylethyl)sulfamoyl]pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45 mg	With lithium hexamethyldisilazane; In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere;	Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1200 mg, 4.45 mmol) was dissolved in dry pyridine (21 mL, 0.98 g/mL, 260.17 mmol). l,l,l-trifluoro-2-methylpropan-2- amine (1131.2 mg, 8.9 mmol) was added and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3- fluoro-l-methyl-4-[(2,2,2-trifluoro-l,l-dimethyl-ethyl)sulfamoyl]pyrrole-2-carboxylate (1.15 g) as a beige powder which was used as such in the next step. Ethyl 3-fluoro-l-methyl-4-[(2,2,2- trifluoro- l,l-dimethyl-ethyl)sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.42 mmol) and (0863) <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (54.55 mg, 0.46 mmol) were dissolved in THF (4.1 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (1.04 mL, 1 M, 1.04 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC (RP SunFire Prep CI 8 OmicronBeta-10muiotaeta,30chi150 mm), mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 188 (45 mg) as a white powder. Method B: Rt: 0.94 min. m/z: 432.1 (M-H)" Exact mass: 433.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.39 (s, 6 H), 3.83 (s, 3 H), 7.58 (d, J=4.4 Hz, 1 H), 7.91 (dd, J=5.6, 1.9 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.47 (br. s., 1 H), 8.63 (d, J=5.7 Hz, 1 H), 10.67 (br. s., 1 H)

Reference： [1]Patent: WO2015/118057,2015,A1 .Location in patent: Page/Page column 122; 123

10
1-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-1H-pyrrole-2-carboxylic acid [ No CAS ]
[ 98139-15-2 ]
N-(2-cyanopyridin-4-yl)-1-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-1H-pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.6 g		l-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-lH-pyrrole-2-carboxylic acid (200 mg, (0182) 0.729 mmol) was dissolved in DMF (1.7 mL) and triethylamine (0.41 mL, 2.9 mmol) and HATU (360 mg, 0.95 mmol) were added. After 10 minutes <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (174 mg, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 42 hours. The mixture was poured into water (50 mL) and the organics were extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (Na2S04) and concentrated to dryness. The residue was purified using silica gel column chromatography (ethyl acetate in heptane from 0 to 100%) followed by prep. HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30 x 150mm), Mobile phase: 0.5% NH4OAc solution in water + 10% CH3CN, MeOH), resulting in compound 1 (4.6 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.54 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.4 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.43 (s, 1 H), 7.66 (d, J=1.3 Hz, 1 H), 7.86 - 8.12 (m, 2 H), 8.26 (d, J=2.0 Hz, 1 H), 8.60 (d, J=5.7 Hz, 1 H), 10.68 (br. s., 1 H). Method A; Rt: 1.22 min. m/z : 374.0 (M-H)~ Exact mass: 375.1.

Reference： [1]Patent: WO2015/118057,2015,A1 .Location in patent: Page/Page column 24

11
(3R*,4R*)-2-isobutyl-1-oxo-3-(thiophen-2-yl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid [ No CAS ]
[ 98139-15-2 ]
C₂₄H₂₂N₄O₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 7950 - 7962

12
C₁₇H₁₃Cl₂NO₃S [ No CAS ]
[ 98139-15-2 ]
5-chloro-N-(2-cyanopyridin-4-yl)-3-((3,5-dimethylphenyl)-sulfonyl)-1H-indole-2-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 6528 - 6547

13
[ 19235-89-3 ]
[ 98139-15-2 ]

Reference： [1]Patent: WO2017/181177,2017,A1

14
4-((diphenylmethylene)amino)picolinonitrile [ No CAS ]
[ 98139-15-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride; In methanol; at 20℃; for 2h;	Into a 50-mL round-bottom flask, was placed 4-[(diphenylmethylidene)amino] pyridine-2-carbonitrile (1.23 g, 2.17 mmol, 1.00 equiv., 50%), hydrogen chloride(2M) (8 mL, 2.00 equiv.), methanol (24 mL). The resulting solution was stirred for 120 min at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 2x10 mL of dichloromethane and the water phase combined. The pH value of the water phase was adjusted to 8 with sodium bicarbonate (sat. solution). The resulting solution was extracted with 3x10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1x20 mL of brine, dried over Na2SC the solids were filtered out. The residue was evaporated and the result solid was dried in an oven under reduced pressure. This resulted in 0.28 g (81%) of 4-aminopyridine-2-carbonitrile as a yellow solid.

Reference： [1]Patent: WO2017/181177,2017,A1 .Location in patent: Paragraph 0518; 0521-0522

15
[ 98139-15-2 ]
N-(2-(aminomethyl)pyridin-4-yl)-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)pyridin-2-amine [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

16
[ 98139-15-2 ]
5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)-N-(2-(((tetrahydro-2H-pyran-4-yl)amino)methyl)pyridin-4-yl)pyridin-2-amine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

17
2-bromo-5-methoxy-4-[3-(pyrrolidin-1-yl)propoxy]pyridine [ No CAS ]
[ 98139-15-2 ]
4-((5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)pyridin-2-yl)amino)picolinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; tert-butyl XPhos; In 1,4-dioxane; at 110℃; for 16h;Sealed tube;	Into a 30-mL sealed tube, was placed 2-bromo-5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridine (314 mg, 1.00 mmol, 1.00 equiv.), <strong>[98139-15-2]4-aminopyridine-2-carbonitrile</strong> (240 mg, 2.01 mmol, 2.00 equiv.), Pd2(dba)3-chloroform (0.1 g, 0.10 equiv.), t-BuXPhos (0.085 g, 0.20 equiv.), Cs2C03 (970 mg, 2.97 mmol, 3.00 equiv.), dioxane (10 mL). The resulting solution was stirred for 16 h at 110 C in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3x30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 1x50 mL of brine, dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (3 mL) was purified by Flash- Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN:Water=l :5 increasing to MeCN:Water=10: l within 120 min; Detector, UV 254 nm. 70 mg product was obtained. This resulted in 70 mg (20%) of 4-([5-methoxy-4-[3- (pyrrolidin-l-yl)propoxy]pyridin-2-yl]amino)pyridine-2-carbonitrile as an off-white solid.

Reference： [1]Patent: WO2017/181177,2017,A1 .Location in patent: Paragraph 0518; 0523-0524

18
[ 98139-15-2 ]
4-(4-(12-β-dihydroartemisinoxymethyl)-1H-1,2,3-triazol-1-yl)-picolinonitrile [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 5978 - 5995

19
[ 98139-15-2 ]
C₆H₃N₅ [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 5978 - 5995

20
1-(naphthalen-1-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid [ No CAS ]
[ 98139-15-2 ]
N-(2-cyanopyridin-4-yl)-1-(naphthalen1-yl)-5-(trifluoromethyl)- 1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With pyridine; trichlorophosphate; at 0℃; for 1h;	P0C13 (0.3 mE) was added dropwise to a solution consisting of 1 -(naphthalen- 1 -yl)-5-(trifluoromethyl)-i Hpyrazole-4-carboxylic acid 2b (150 mg, 0.490 mmol), <strong>[98139-15-2]4-aminopicolinonitrile</strong> (64.2 mg, 0.53 9 mmol) and pyridine (5 mE). The mixture was stirred at 0 C. for 1 h. The resulting mixture was concentrated under reduced pressure to give a crude product, which was purified by preparative HPEC (40% to 70% (v/v) ACN and H20 with 0.05% NH3) to afford compound 1. Compound 1 was concentrated to dryness under reduced pressure (101.30 mg, 5 1%). ECMS (ESI): RT=5.45 mm, mass calcd. for C2,H,2F3N50 407.348, mlz found 408.0 [M+H]. ?H NMR (400 MHz, DMSO-d5) oe ppm 11.31 (s, 1H), 8.71 (d, J=5.2 Hz, 1H), 8.56 (s, 1H), 8.30 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H),8.00 (d, J=4.0 Hz, 1H), 7.83-7.77 (m, 1H), 7.76-7.62 (m, 3H), 7.14 (d, J=8.0 Hz, 1H).

Reference： [1]Patent: US2018/170909,2018,A1 .Location in patent: Paragraph 1296; 1297

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[ CAS No. 98139-15-2 ] {[proInfo.proName]}

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[ 98139-15-2 ] Synthesis Path-Upstream 1~2

[ 98139-15-2 ] Synthesis Path-Downstream 1~20

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Amines

Nitriles

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Pyridines

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