[ CAS No. 1002309-47-8 ] {[proInfo.proName]}

Name: 1002309-47-8|6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole|98%
Brand: Ambeed
SKU: A121051
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Quality Control of [ 1002309-47-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1002309-47-8 ]

SDS Specification

Alternatived Products of [ 1002309-47-8 ]

Product Details of [ 1002309-47-8 ]

CAS No. :	1002309-47-8	MDL No. :	MFCD12408395
Formula :	C₁₃H₁₆BNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VLJNKSRMMHATGX-UHFFFAOYSA-N
M.W :	261.15	Pubchem ID :	46739806
Synonyms :

Calculated chemistry of [ 1002309-47-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.46
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	76.1
TPSA :	59.59 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.37
Log Po/w (WLOGP) :	2.6
Log Po/w (MLOGP) :	1.5
Log Po/w (SILICOS-IT) :	3.0
Consensus Log Po/w :	2.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.89
Solubility :	0.0339 mg/ml ; 0.00013 mol/l
Class :	Soluble
Log S (Ali) :	-4.3
Solubility :	0.0131 mg/ml ; 0.0000502 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.57
Solubility :	0.007 mg/ml ; 0.0000268 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.9

Safety of [ 1002309-47-8 ]

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 [ 1002309-47-8 ]

* 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 [ 1002309-47-8 ]

[ 1002309-47-8 ] Synthesis Path-Downstream 1~14

2
[ 53218-26-1 ]
[ 73183-34-3 ]
[ 1002309-47-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 95℃; for 18h;Inert atmosphere; Sealed flask;	6-bromobenzo[d]thiazole (0.428 g; 2 mmol), potassium acetate (0.687 g; 7.0 mmol) and bis[pinacolato]diborane (0.762 g; 3.0 mmol) were placed in a 20 mL microwave vial, dissolved in dry DMF (13 mL) and the flask was purged with nitrogen. The catalyst [1 ,1 '- Bis(diphenylphosphino)ferrocene]palladium(ll) chloride, complex with dichloromethane (0.169 g; 0.20 mmol) was added, the flask was again purged with argon, sealed and the reaction was heated at 950C for 18 h. The reaction mixture was diluted with water and the suspension was extracted twice with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (10 -80 %) in heptane furnished 0.510 g (98 %) of the title compound.1H NMR (DMSO-d6) delta 9.49 (s, 1 H); 8.50 (s, 1 H); 8.09 (d, J = 8.1 Hz, 1 H); 7.80 (dd, J = 8.1 , 0.6 Hz, 1 H); 1.33 (s, 12 H).
90%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere;	A suspension of 6-bromo-benzothiazole (300 mg, 1.40 mmol), bis(pinacolato)diboron (427 mg, 1.68 mmol) and potassium acetate (KOAc)(412 mL, 4.20 mmol) in N,N-dimethylformamide (DMF, 6 mL) was added to PdCl2(dppf)2 (57 mg, 0.07 mmol), and the mixture was stirred at 100 C under N2 for 4 hours. After cooling to room temperature, the mixture was diluted with brine and EtOAc, and stirred for 5 minutes. After separating the organic layer, the aqueous layer was extracted three times with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, and concentrated under a reduced pressure. The residue was purified by MPLC on silica gel eluting with EtOAC/hexane (1/20) to obtain the title compound (329 mg, 90%) as a white solid. 1H NMR (300 MHz, CDC13) delta 9.06 (s, 1H), 8.46 (s, lH), 8.13 (d, 1H), 7.94 (d, 1H), 1.38 (s, 12H).
77%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 90℃; for 16.5833h;	Example 48: Synthesis of boronate fragment 48b (used for the preparation of 1136)48a 48bStep 1 :A stirred DMF (5 mL) solution of the arylbromide 48a (0.152 g, 0.71 mmol), potassium acetate (0.209 g, 2.1 mmol) and bis(pinacolato)diborane (0.234 g, 0.92 mmol) is degassed by bubbling Ar through the solution for 20 min. PdCI2(dppf)-DCM (87 mg, 0.11 mmol) is added and degassing is continued for 15 min. The system is sealed (Teflon screw cap vessel) under Ar and heated to 9O0C for 16 h. The reaction mixture is allowed to cool to RT, dilute with EtOAc (150 mL), washed with brine (3 x 100 mL) and water (2 x 100 mL), dried over anhydrous MgSO4, filtered and concentrated to dryness. The residue is purified by CombiFlash Companion <n="108"/>(EtOAc/hexanes) to give the desired boronate 48b (144 mg, 77% yield) as a yellowish solid.

77%		A stirred DMF (5 mL) solution of the arylbromide 46e (0 152 g, 0 71 mmol), potassium acetate (0 209 g, 2 1 mmol) and biotas(piotanacolato)diotaborane (0 234 g, 0 92 mmol) is degassed by bubbling Ar through the solution for 20 mm PdCI2(dppf)-DCM (87 mg, 0 11 mmol) is added and degassing is continued for 15 mm The system is sealed (Teflon screw cap vessel) under Ar and heated to 9O0C for 16 h The <n="113"/>reaction mixture is allowed to cool to RT, dilute with EtOAc (150 ml_), washed with brine (3 x 100 mL) and water (2 x 100 ml_), dried over anhydrous MgSO4, filtered and concentrated to dryness. The residue is purified by CombiFlash Companion (EtOAc/hexanes) to give the desired boronate 46b (144 mg, 77% yield) as a yellowish solid.
48%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 16h;Inert atmosphere;	The mixture of 6-bromobenzo[djthiazole (2-83, 200 mg, 0.94 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (239 mg, 0.94 mmol), KOAc (184mg, 1.88 mmol), Pd(dppf)C12 (68 mg, 0.094 mmol) in 1,4-dioxane (5 ml) was stirred for 16 h at 105 C under N2, after completion, added water, the mixture was extracted with ethyl acetate (50 mL x 3), combined the organic phase, concentrated under reduced pressure, the residue was purified by silica gel chromatography (Pet Ether/ethyl acetate = 10/1) to obtain title compound 2-84 (yellow solid, 120 mg, 48% yield). LCMS: 262(M + H) .
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 4h;Inert atmosphere;	The A12-1 (43mg, 0.20mmol) was dissolved in dioxane (4mL), was added bis (pinacolato) borate (61mg, 0.24mmol), KOAc (59mg,0.60mmol), Pd (dppf) 2Cl2 (16mg, 0.02mmol), purged with nitrogen, 90 stirred for 4 hours, cooled to room temperature, suction filtered through Celite, the filterWas spin dried to give crude black oil (126mg), was used directly in the next step.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100℃; for 7h;Inert atmosphere;	General procedure: Under argon protection,Add to the 100mL single-mouth bottle5-bromo-1-methyl-6-(trifluoromethyl)-1H-indazole(500mg, 1.79mmol),Bis(pinacolato)diboron(685.2mg, 2.69mmol),Potassium acetate (352.5 mg, 3.58 mmol),Pd(dppf)Cl2 (131.6 mg, 0.179 mmol)And dioxane (15mL), plus,The temperature was raised to 100 C for 7 h.The reaction system was cooled to room temperature, and 20 mL of water was added to the reaction solution.The aqueous phase was extracted three times with ethyl acetate (50 mL×3).The crude product was purified by column chromatography.The product was eluted with PE/EA = 10/1, and the product was collected and concentrated to give 300 mg of pale yellow oil, yield: 51.1%.

Reference： [1]Patent: WO2011/15641,2011,A1 .Location in patent: Page/Page column 132
[2]Patent: WO2013/9140,2013,A2 .Location in patent: Page/Page column 26
[3]Patent: WO2009/62285,2009,A1 .Location in patent: Page/Page column 106-107
[4]Patent: WO2009/62288,2009,A1 .Location in patent: Page/Page column 111-112
[5]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276
[6]Patent: WO2016/161145,2016,A1 .Location in patent: Paragraph 00756
[7]Patent: CN105254613,2016,A .Location in patent: Paragraph 0119; 0120; 0121
[8]Patent: CN108707139,2018,A .Location in patent: Paragraph 0612; 0614; 0659; 0660; 0661; 0662

3
[ 1002309-47-8 ]
[ 1168134-90-4 ]
[ 1168134-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 20 - 80℃; for 14h;	Step 2Ethyl 2-(3-(benzo[d]thiazol-6-yl)-5-chloro-4-(cyclopropylmethoxy)phenyl)-4- methylpentanoate <n="281"/>To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)-phenyl)-4- methyl pentanoate (0.5 g, 1.239 mmol) in a mixture of DMF (10 mL) and water (5 mL) were added Cs2CO3 (1.4 g, 4.325 mmol), Pd (TPP) 4 (286 mg, 2.475 mmol) and 6- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzo[d]thiazole (355 mg, 1.363 mmol) at RT under N2 atmosphere and the resulting mixture was stirred at 80 C for 14 h. After completion of starting material (by TLC), the solids were removed via filtration through a bed of Celite was washing with EtOAc (3 x 100 mL). The combined organic layers were washed with water (3 x 50 mL), brine and dried over anhydrous Na2SO^ filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to afford ethyl 2-(3-(benzo[d]thiazol-6-yl)-5-chloro-4- (cyclopropylmethoxy)phenyl)-4-methylpentanoate (100 mg) as an off white solid.
100 mg	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 14h;Inert atmosphere;	To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-(cyclopropy3methoxy)- phenyl)-4-meth.yl pentanoate (0.5 g, 1 .239 mmol) in a mixture of DMF (1 0 ml.) and water (5 niL) were added Cs2C03(1.4 g, 4.325 mmol), Pd (TPP)4(286 mg, 2.475 mmol) and 6~ (4,4,5,5-tetrameth.y1-l,3,2-dioxaborolan-2-yl)benzo[d]thiazole (355 mg, 1.363 mmol) at RT under N2atmosphere and the resulting mixture was stirred at 80 C for 14 h. After completion of starting material (by TLC), the solids were removed via filtration through a bed of Celite was washing with EtOAc (3 x 100 mL). The combined organic layers were washed with water (3 x 50 mL), brine and dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to afford ethyl 2-(3-(benzo[d]thiazol-6-y3)-5- chloro-4- (cyclopropyimethoxy)phenyl)-4-m.ethylpentanoate (100 mg) as an off white solid.

Reference： [1]Patent: WO2009/86277,2009,A1 .Location in patent: Page/Page column 279-280
[2]Patent: WO2013/106328,2013,A1 .Location in patent: Paragraph 0757; 0758

4
[ 1002309-47-8 ]
[ 1418306-01-0 ]
[ 1418306-14-5 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 100℃; for 13h;Inert atmosphere;	Pd(PPh3)4 (17.9 mg, 0.016 mmol) was added to a mixture of 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzothiazole (Intermediate 2, 97.0 mg, 0.37 mmol), 1-[5-bromo-6-(6-methyl-pyridin-2-yl)-2,3-dihydro-imidazo[1,2-a]imidazol-1-yl]-ethanone (Intermediate 12, 100 mg, 0.31 mmol), K2CO3 (85.7 mg, 0.62 mmol) in toluene (4.5 mL) and EtOH (0.23 mL), and the mixture was stirred at 100 C under N2 for 13 hours. After cooling to room temperature, the mixture was filtered through celite, washed with CH2Cl2, and concentrated under a reduced pressure. The residue was purified by MPLC on NH silica gel eluting with CH2Cl2/hexane/EtOAc (3/1/0.5 ? 3/1/1) and recrysallization from CH2Cl2/hexane to obtain the coupled compound (49.2 mg, 42%) as a white solid.

Reference： [1]Patent: WO2013/9140,2013,A2 .Location in patent: Page/Page column 40; 41

5
[ 1002309-47-8 ]
[ 1418306-01-0 ]
[ 1418305-53-9 ]

Reference： [1]Patent: WO2013/9140,2013,A2

6
[ 1002309-47-8 ]
[ 1431773-82-8 ]
[ 1431773-04-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; XPhos; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Sealed tube;	A mixture of (S)-6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.15 g, 0.456 mmol), <strong>[1002309-47-8]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole</strong> (0.119 g, 0.456 mmol), Pd2(dba)3 (0.052 g, 0.09 mmol), X-phos (0.087 g, 0.18 mmol) and Na2CO3 (0.145 g, 1.368 mmol) in dioxane (20 mL) and water (5 mL) was heated to 100 C. for 16 h in a sealed tube under N2 atmosphere then concentrated in vacuo. The residue was purified by chromatography (silica gel, 15 g, 200-300 mesh, ethyl acetate:petroleum ether=1:5) to afford (S)-6-(benzo[d]thiazol-6-yl)-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (58 mg, 51%) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 9.71 (s, 1H), 9.49 (s, 1H), 8.91 (s, 1H), 8.69 (s, 1H), 8.23-8.08 (m, 3H), 7.66 (s, 1H), 7.43 (t, 1H, J=7.8 Hz), 6.74 (d, 1H, J=7.8 Hz), 6.06 (d, 1H, J=7.8 Hz), 4.26-4.23 (m, 1H), 3.59-3.55 (m, 1H), 3.44-3.40 (m, 1H), 2.08-1.98 (m, 3H), 1.69-1.66 (m, 1H), 1.09 (d, 3H, J=6.3 Hz). LC-MS: [M+H]+, 428, tR=1.997 min, HPLC: 95.07% at 214 nm, 98.34% at 254 nm, tR=4.349 min.
51%	With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; XPhos; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Sealed tube;	A mixture of (5)-6-chloro-N-(6-(2-methylpyrrolidin-l-yl)pyridin-2-yl)imidazo[l ,2-b]pyridazin- 8- amine (0.15 g, 0.456 mmol), 6-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzo[d]thiazole (0.1 19 g, 0.456 mmol), Pd2(dba)3 (0.052 g, 0.09 mmol), X-phos (0.087 g, 0.18 mmol) and Na2C03 (0.145 g, 1.368 mmol) in dioxane (20 mL) and water (5 mL) was heated to 100 C for 16 h in a sealed tube under N2 atmosphere then concentrated in vacuo. The residue was purified by chromatography (silica gel, 15 g, 200-300 mesh, ethyl acetate : petroleum ether = 1 : 5 ) to afford (S)-6-(benzo [d]thiazo l-6-yl)-N-(6-(2-methylpyrrolidin- 1 -yl)pyridin-2-yl)imidazo [1 ,2- b]pyridazin-8-amine (58 mg, 51 %) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 9.71 (s, 1H), 9.49 (s, 1H), 8.91 (s, 1H), 8.69 (s, 1H), 8.23 - 8.08 (m, 3H), 7.66 (s, 1H), 7.43 (t, 1H, J = 7.8 Hz), 6.74 (d, 1H, J= 7.8 Hz), 6.06 (d, 1H, J= 7.8 Hz), 4.26 - 4.23 (m, 1H), 3.59 - 3.55 (m, 1H), 3.44 - 3.40 (m, 1H), 2.08 - 1.98 (m, 3H), 1.69 - 1.66 (m, 1H), 1.09 (d, 3H, J= 6.3 Hz). LC-MS : [M+H]+, 428, tR = 1.997 min, HPLC: 95.07 % at 214nm, 98.34 % at 254nm, tR = 4.349 min.

Reference： [1]Patent: US2013/109661,2013,A1 .Location in patent: Paragraph 0453-0454
[2]Patent: WO2013/64445,2013,A1 .Location in patent: Page/Page column 115

7
[ 1002309-47-8 ]
C₁₄H₁₀BrFN₂O₂ [ No CAS ]
7-(benzo[d]thiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one [ No CAS ]

Reference： [1]Patent: WO2015/157093,2015,A1 .Location in patent: Paragraph 0088; 0453

8
[ 1002309-47-8 ]
C₁₇H₁₄ClFN₄ [ No CAS ]
C₂₄H₁₈FN₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23 mg	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	The A1-4 (50mg, 0.15mmol), A12-2 (126mg, crude) was dissolved in dioxane / water (5mL / 1mL), was added potassium carbonate (84mg,0.61 mmol), palladium tetrakistriphenylphosphine phosphorus (17mg, 0.015mmol), purged with nitrogen, stirred overnight at 100 deg. C, cooled to room temperature, suction filtered through Celite, the filterExtracted with ethyl acetate (15mL) diluted with anhydrous sodium sulfate, and sodium sulfate was filtered, spin-dry the solvent, the residue was purified by column chromatography (dichloromethane: methanol= 100: 1-50: 1) to afford an off-white solid (28mg, 43%). After parsing NMR spectrum (map data in Table 1), the resulting solid was compound

Reference： [1]Patent: CN105254613,2016,A .Location in patent: Paragraph 0119; 0122; 0123

9
[ 1002309-47-8 ]
[ 1391980-02-1 ]
5-(benzo[d]thiazol-6-yl)-4-(3-chlorophenyl)thiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.5h;Microwave irradiation;	General procedure: Step 4: A mixture of 5-bromo-4-(3-chlorophenyl)thiazol-2-amine (0.04 g, 0.14 mmol), <strong>[1002309-47-8]6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole</strong> (0.05 g, 0.18 mmol), tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol), and 2.0 M of aqueous Na2CO3 (0.2 mL) in 1,2-dimethoxyethane (1.4 mL), EtOH (0.6 mL) and water (0.4 mL) was irradiated under microwave at 150 C. for 0.5 h. The mixture was then concentrated under reduced pressure to give a residue, which was purified by chromatography eluting with ethyl acetate to provide 5-(benzo[d]thiazol-6-yl)-4-(3-chlorophenyl)thiazol-2-amine as a pale white solid (0.03 g, 55%).

Reference： [1]Patent: US2016/257690,2016,A1 .Location in patent: Paragraph 0729

10
[ 1002309-47-8 ]
8-chloro-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]
8-(1,3-benzothiazol-6-yl)-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 180℃; for 0.5h;Inert atmosphere; Sealed tube; Microwave irradiation;	A 5-mL microwave vessel is charged with 8-chloro-A -(4- methanesulfonylpyridin-3-yl)quinoxalin-6-amine (Intermediate 3B, 80 mg; 0.24 mmol; 1 eq.), 6-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- benzothiazole (75 mg; 0.29 mmol; 1.20 eq.), dioxane (3 mL) and a sodium carbonate 2 M aq. solution (0.24 mL; 0.48 mmol; 2 eq.). The mixture is degassed by sonication and bubbling argon for 10 min. Tetrakis(triphenylphosphine)palladium(0) (29 mg; 0.02 mmol; 0.10 eq.) is added and the vessel is sealed. The reaction mixture is heated under microwave irradiation at 180 C for 30 minutes. The reaction mixture is filtered through a pad of celite and the filtrate is diluted with DCM. The organic phase is washed with water and brine, dried over Na2S04 and concentrated. The residue is purified by FCC (0-5% MeOH in DCM) and by FCC (0-5% MeOH in EtOAc) to give 8-(1 ,3-benzothiazol-6-yl)-/v"-(4- methanesulfonylpyridin-3-yl)quinoxalin-6-amine (16 mg; 0.04 mmol; yield: 15%; bright yellow powder; HPLC purity: 97.6%).

Reference： [1]Patent: WO2016/180537,2016,A1 .Location in patent: Page/Page column 106; 107
[2]ChemMedChem,2019,vol. 14,p. 169 - 181

11
[ 1002309-47-8 ]
[ 1396776-45-6 ]
6-(2-amino-5-(benzo[d]thiazo1-6-yl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In tetrahydrofuran; water; at 65℃; for 16h;Inert atmosphere;	The mixture of 6-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzo [djthiazole (2-84, 80 mg, 0.31 mmol) and 6-(2-amino-5-(benzo[djthiazol-6-yl)pyridin-3-yl)-3 ,4- dihydroisoquinolin-1(2H)-one (2-4, 97 mg, 0.31 mmol), K3P04 (129 mg, 0.6lmmol), Pd(PPh3)2C12 (21 mg, 0.03 1 mmol) in THF (2 mL) and H20 (0.1 mL) was stirred at 65 C for 16 h under N2, after completion, filtered, concentrated under reduced pressure, the residue was purified by prep-HPLC (C18 column, CH3CN/H20, containing 0.05% TFA) to get title compound 1-44 (white solid, 11 mg, 10%). LCMS: 373 (M + H) HPLC: 100% (254 nm); ?H NMR (DMSO-d6, 400 MHz) oe 9.40 (s, 1H), 8.49 (d, J 1.5 Hz, 1H), 8.44 (d, J 2.4 Hz, 1H), 8.10 (d, J= 8.6 Hz, 1H), 8.01 -7.70 (m, 3H), 7.61 - 7.42 (m, 2H), 5.99 (s, 2H), 3.63 -3.36 (m, 2H), 2.98 (t, J 6.5 Hz, 2H).

Reference： [1]Patent: WO2016/161145,2016,A1 .Location in patent: Paragraph 00757

12
[ 1002309-47-8 ]
6-[18F]fluorobenzo[d]thiazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276

13
[ 1002309-47-8 ]
1-((2S)-2-(5-iodo-1H-imidazol-2-yl)-4-((tetrahydrofuran-3-yl)methyl)piperazin-1-yl)-2-(6-methoxy-2-methyl-1H-benzo[d]imidazol-1-yl)ethan-1-one [ No CAS ]
1-((2S)-2-(5-(benzo[d]thiazol-6-yl)-1H-imidazol-2-yl)-4-((tetrahydrofuran-3-yl)methyl)piperazin-1-yl)-2- (6-methoxy-2-methyl-1H-benzo[d]imidazol-1-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,2-dimethoxyethane; water; at 110℃; for 1h;	Y7 (1.0 eq) and 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3-benzothiazole (1.2 eq) were dissolved in DME (0.03 M) and obtained solution was then degassed and K2C03 (3 eq) in H20 (0.03 M) was added followed by PdCl2(dppf)DCM (0.5 eq). The mixture was heated at 110 C and stirred for 1 h then filtered, concentrated and purified by RP-HPLC (MeCN, H20 + 0.1% TFA) to give the title compound (36%) as a white solid. H-NMR (400 MHz, 300 K, CD3CN) delta (80 :20* mixture of rotamers) 9.14* and 9.12 (s, 1H), 8.60- 8.55 (d, 1H, J= 4.4 Hz), 8.12 (d, 1H, J= 8.4 Hz), 7.96-7.93 (m, 1H), 7.7 (d, 1H, J= 8.9 Hz), 7.60 (s, 1H), 7.25 (s, 1H), 7.11 (dd, 1H, J= 2.5, 8.9 Hz), 6.08 and 5.81 (brs, 1H), 5.56-5.51 *, 5.41-5.28 (m, 2H), 4.14-3.59 (m, overlapped with H20 + TFA, 7H), 3.85 (s, 3H), 3.52-3.48 (m, 1H), 3.34-3.13 (m, 4H), 2.74 (s, 3H), 2.24-2.10 (m, 1H), 1.89-1.81 (m, 1H), 1.73-1.64 (m, 1H). MS (ES+) m/z 572 (M+H)+.

Reference： [1]Patent: WO2018/115275,2018,A1 .Location in patent: Page/Page column 69; 70

14
[ 1002309-47-8 ]
6-bromo-5-chloroimidazo[1,2-a]pyrazin-8-amine [ No CAS ]
5,6-bis(1,3-benzothiazol-6-yl)imidazo[1,2-a]pyrazin-8-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 150℃; for 2h;Inert atmosphere;	In a pressure tube were mixed 6-bromo-5-chloroimidazo[1 ,2-a]pyrazin-8-amine (200 mg, 0.96 mmol), 4-cyanophenylboronic acid (155 mg, 1.06 mmol, 1.1 equiv.) and Na2CO3 (122 mg, 1.15 mmol, 1.2 equiv.) in a 10:1 mixture of 1,4-dioxane:water (6 mL). The reaction mixture wassparged with argon for 10 mm. Pd(PPh3)4 (55 mg, 0.05 mmol, 5 mol%) was then added and the tube was capped and the reaction mixture was warmed to 100C and stirred overnight. After that time, remaining amount of SM was observed by LCMS therefore additional portion of boronic acid (15 mg, 0.11 mmol, 0.1 equiv.) and the reaction mixture was sparged for 5 mm followed by the addition of another portion of Pd(PPh3)4 (27 mg, 0.025 mmol, 2.5 mol%). The tube was capped and the reaction mixture was warmed to 10000 and stirred overnight. After that time, the reaction mixture was then cooled down to r.t., filtered through Celite and rinsed with EtOAc. The organic solution was washed with water and brine and aqueous layer was extracted with EtOAc. Separated organic layer was dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure to afford the crude material as a brown residue. The obtained crude material was purified by flash chromatography on ON-silica eluting with hexane and DOM to lead to the title product (145 mg, 0.54 mmol, 56%) as a pale yellow solid. ESl-MS:269.90 [M+H]+.

Reference： [1]Patent: WO2019/2606,2019,A1 .Location in patent: Page/Page column 93; 94; 113

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[ CAS No. 1002309-47-8 ] {[proInfo.proName]}

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[ 1002309-47-8 ] Synthesis Path-Downstream 1~14

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Organoboron

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Benzothiazoles

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