[ CAS No. 153747-97-8 ]

Name: 153747-97-8|tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate|96%
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Quality Control of [ 153747-97-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 153747-97-8 ]

Product Details of [ 153747-97-8 ]

CAS No. :	153747-97-8	MDL No. :	MFCD07369772
Formula :	C₁₄H₂₀BrN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DSLVSFMWCDGZIL-UHFFFAOYSA-N
M.W :	342.23 g/mol	Pubchem ID :	11244775
Synonyms :

Calculated chemistry of [ 153747-97-8 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.57
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	89.14
TPSA :	45.67 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.27
Log Po/w (XLOGP3) :	2.66
Log Po/w (WLOGP) :	2.14
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	1.8
Consensus Log Po/w :	2.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.6
Solubility :	0.0868 mg/ml ; 0.000254 mol/l
Class :	Soluble
Log S (Ali) :	-3.27
Solubility :	0.184 mg/ml ; 0.000536 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.52
Solubility :	0.102 mg/ml ; 0.000299 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.7

Safety of [ 153747-97-8 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P301+P310-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 153747-97-8 ]

* 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.

Upstream synthesis route of [ 153747-97-8 ]
Downstream synthetic route of [ 153747-97-8 ]

[ 153747-97-8 ] Synthesis Path-Upstream 1~9

1
[ 624-28-2 ]
[ 57260-71-6 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; sodium t-butanolate In toluene at 80℃; for 4 h; Sealed tube; Inert atmosphere	To a stirred solution of 2,5-dibromopyridine (2 g, 10.7 mmol), sodium tert-butoxide (1.6 g,16.6 mmol), xantphos (400 mg, 0.7 mmol) and toluene (100 mL) in sealed tube argon waspurged for 5 min. To the reaction mixture tert-butyl piperazine-1-carboxylate (3 .4 g, 14.30mmol) followed by Pd2(dba)3 (200 mg, 0.21 mmol) was added and heated at 80 °C for 4 h(TLC indicated complete consumption of starting material). The reaction mixture was dilutedwith EtOAc (200 mL), water (100 mL), filtered through Celite bed and washed with EtOAc(2 x 30 mL). The combined organic extracts were washed with brine (50 mL), dried overNa2S04 and concentrated under reduced pressure to give the crude product which waspurified by column chromatography (100-200 silica gel, 50 g, 10-20percent EtOAc-hexanes) toafford tert-butyl4-(5-bromo-2-pyridyl)piperazine-1-carboxylate (3 g, 82percent) as a yellow solid.LCMS (ESI+ ): m/z: 342.57 [M+Ht.

Reference： [1] Organic Letters, 2003, vol. 5, # 24, p. 4611 - 4614
[2] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 123
[3] Patent: WO2007/20888, 2007, A1, . Location in patent: Page/Page column 45-46
[4] Patent: US2006/293310, 2006, A1, . Location in patent: Page/Page column 5

2
[ 53939-30-3 ]
[ 57260-71-6 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
81.5%	With potassium carbonate In acetonitrile at 110℃; for 12 h;	General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 °C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7percent).; The title compound was prepared using tert-butyl piperazine-1-carboxylate (1.45 g, 7.79 mmol),5-bromo-2-chloropyridine (1.00 g, 5.20 mmol) and potassium carbonate (1.44 g, 10.39 mmol) in acetonitrile (30 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (1.45 g, 8 1.5percent).MS (ESI, pos. ion) m/z: 342.1 [M+H] and‘H NMR (600 MHz, CDC13): (ppm) 8.17 (d, J 2.4 Hz, 1H), 7.52 (dd, J 9.0, 2.5 Hz, 1H), 6.52 (d, J 9.0 Hz, 1H), 3.55 - 3.49 (m, 4H), 3.49 - 3.45 (m, 4H), 1.46 (s, 9H).
58.8%	at 80℃; for 14 h;	To a stirred solution of 1-Boc piperazine (10.6 g, 57.29 mmol, Symax fine chemicals) in dryDMF (lOOmL), TEA (14.43 mL, 103.39 mmol) and 5-bromo-2-chloropyrimidine (10 g, 52.08mmol, Oakwood chemicals) were added and the reaction mixture was stirred at 80°C for 14h. It was cooled down to rt and poured on iced water (100 mL). The resulting precipitatewas filtered and washed with hexane (50 mL) to afford the title compound. Yield: 58.8percent(10 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 68.60(s, IH), 8.13 (dd, J= 8.6, 2.4Hz, IH), 7.54 (dd, J = 8.4, 0.4 Hz, IH), 3.22-3.20 (m, 4H), 2.61-2.59 (m, 4H), 1.42 (5, 9H).LCMS: (Method A) 343.9 (M +2H), Rt. 5.58 mm, 98.9percent (Max).
58.8%	With triethylamine In N,N-dimethyl-formamide at 80℃; for 14 h;	To a stirred solution of 1-Boc piperazine (10.6 g, 57.29 mmol, Symax fine chemicals) in dry DMF (100mL), TEA (14.43 mL, 103.39 mmol) and 5-bromo-2-chloropyridine (10 g, 52.08 mmol, Oakwood chemicals) were added and the reaction mixture was stirred at 80°C for 14 h. It was cooled down to rt and poured on iced water (100 mL). The resulting precipitate was filtered and washed with hexane (50 mL) to afford the title compound. Yield: 58.8percent (10 g, off white solid). ¹H NMR (400 MHz, DMSO-d₆): δ 8.60 (s, 1 H), 8.13 (dd, J = 8.6, 2.4 Hz, 1 H), 7.54 (dd, J = 8.4, 0.4 Hz, 1 H), 3.22-3.20 (m, 4H), 2.61 -2.59 (m, 4H), 1.42 (s, 9H). LCMS: (Method A) 343.9 (M +2H), Rt. 5.58 min, 98.9percent (Max).

Reference： [1] Patent: WO2016/192657, 2016, A1, . Location in patent: Page/Page column 65
[2] Patent: WO2017/144633, 2017, A1, . Location in patent: Page/Page column 111
[3] Patent: WO2017/144639, 2017, A1, . Location in patent: Page/Page column 96

3
[ 766-11-0 ]
[ 57260-71-6 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
87.66%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12 h;	Step 1: K₂CO₃ (2.76 g, 20 mmol) was added into a mixture of 270-2 (1.76 g, 10 mmol) and 270-1 (2.24 g, 12 mmol) in DMF (20 mL). The mixture was stirred at 110°C for 12h, poured into H₂O (100 mL). The obtained mixture was extracted with EtOAc (150 mL×3). The organic phases were combined and washed with brines (150 mL), dried over anhydrous sodium sulfate, filtrated, and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=7:1) to deliver 270-3 (3 g, yield 87.66percent) as colorless oil. MS ESI calcd for C₁₄H₂OBrN₃O₂ [M+H]⁺ 342, found 342.

Reference： [1] Patent: EP3124482, 2017, A1, . Location in patent: Paragraph 0711; 0712
[2] Patent: US2012/184520, 2012, A1, . Location in patent: Page/Page column 17

4
[ 24424-99-5 ]
[ 73406-97-0 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine In dichloromethane at 0 - 20℃;	[0949] To a solution ofcompound 90a (125 g, 516 mmol) inDCM (300mL), TEA (104 g, 1.03 mol) was added, followedby (BOC) 2 0 (135 g, 619 mmol) in portions with stirring at ooC. The resulting mixture was stirred overnight at room temperature. The reaction was then quenched with water (1 00mL), and the product was extracted with DCM (3x150 mL).The combined organic layers were concentrated underreduced pressure to obtain compound 90b as a white solid(125 g, 71percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C14H20BrN3 0 2 : 342.1 (M+H). found 342.1.

Reference： [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0948-0949
[2] Patent: CN104650049, 2018, B, . Location in patent: Paragraph 0359; 0360

5
[ 53939-30-3 ]
[ 57260-71-6 ]
[ 633283-53-1 ]
[ 153747-97-8 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 24, p. 4611 - 4614

6
[ 53939-30-3 ]
[ 153747-97-8 ]

Reference： [1] Patent: US2014/364414, 2014, A1,

7
[ 766-11-0 ]
[ 153747-97-8 ]

Reference： [1] Patent: CN104650049, 2018, B,

8
[ 73183-34-3 ]
[ 153747-97-8 ]
[ 496786-98-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; Inert atmosphere	[0951] A solution ofcompound 90b (125 g, 366 mmol) inDMF (1.30 L)was treatedwith, 4,4,4',4',5,5,5',5'-octamethyl2,2'-bi(1,3,2-dioxaborolane) (186 g, 732 mmol), Pd(OAc) 2(4.09 g, 18.3 mmol), PPh3 (19.2 g, 73.2 mmol) and KOAc(108 g, 1.10 mol) under a nitrogen atmosphere. The resultingmixture was stirred overnight at 80° C. Upon cooling to roomtemperature, the solids were collected by filtration. The filtrate was concentratedunderreduced pressure, and the resultant residue was purified by flash colunm chromatography onsilica gel (EtOAc/petroleum ether (1 :50 v/v)) to obtain compound 90c as a white solid (80.0 g, 56percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H32BN3 0 4 : 390.2(M+H). found 390.2.
2.55 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In dimethyl sulfoxide at 80℃; for 2 h; Inert atmosphere	Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (2.0 g, 5.84 mmol),Bis(boronic acid) pinacol ester (2.2 g, 8.77 mmol) andPotassium acetate (1.72 g, 17.53 mmol)To a solution of dimethyl sulfoxide (10 mL) was added Pd(dppf)Cl2.CH2Cl2 (473.0 mg, 0.58 mmol).The reaction was heated to 80°C and stirred for 2 hours.Cool toDiluted with ethyl acetate (100 mL) at room temperature and filtered through celite. The filtrate was washed with saturated brine (100 mL x 4), anhydrousSodium sulfate was dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 3/1) to give the title compoundThe product was an off-white solid (2.55 g, 112percent).

Reference： [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0950-0951
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5361 - 5379
[3] Patent: US2013/225548, 2013, A1, . Location in patent: Paragraph 0531; 0632
[4] Patent: CN104650049, 2018, B, . Location in patent: Paragraph 0426; 0427

9
[ 73183-34-3 ]
[ 153747-97-8 ]
[ 919347-67-4 ]
[ 496786-98-2 ]

Reference： [1] Patent: WO2015/88045, 2015, A1, . Location in patent: Paragraph 0239
[2] Patent: US2017/8885, 2017, A1, . Location in patent: Paragraph 0656; 0658
[3] Patent: WO2017/38909, 2017, A1, . Location in patent: Paragraph 0308; 0309; 0311

[ 153747-97-8 ] Synthesis Path-Downstream 1~58

Yield	Reaction Conditions	Operation in experiment
		A suspension of the bromopyridine (7.00 g, 28.91 mmol) in THF (60 ml) at room temperature was treated with di-tert-butyldicarbonate (6.30 g, 28.90 mmol) and the resulting mixture stirred for 2 h, then evaporated and the crude product purified by recrystallisation (ethanol-water) to afford the 5-Bromo-2-(4-tert-butoxycarbonylpiperazin-1-yl)pyridine (8.76 g) as a beige solid m.p. 88-90. deltaH (CDCl3) 1.47 (9H, s), 3.50 (8H, m), 6.52 (1H, d, J 9.0 Hz), 7.52 (1H, dd, J 9.0, 2.5 Hz) and 8.18 (1H, d, J 2.5 Hz).

2
[ 153747-97-8 ]
1-(5-bromo-pyridin-2-yl)piperazine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; isopropyl alcohol; In 1.4-dioxane; at 60℃; for 3h;	3.2.; 1-(5-bromo-2-pyridyl)piperazine 49 ml (272 mmol) of a solution of hydrochloric acid (6N) in isopropanol are added at room temperature to a solution of 18.60 g (54.40 mmol) of 1,1-dimethyl-ethyl 4-(5-bromo-2-pyridyl)-1-piperazinecarboxylate, obtained in step 3.1., in 100 ml of 1.4-dioxane. The reaction mixture is then maintained at about 60 C. for 3 hours. The mixture is concentrated to dryness under reduced pressure. The dihydrochloride obtained is taken up in 200 ml of dichloromethane and 200 ml of water, followed by portionwise addition, with stirring, of 10 g of sodium hydrogen carbonate. The phases are separated by settling, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. 12 g of product are obtained in the form of a white solid. m.p. ( C.): 72 C.

Reference： [1]Patent: US2006/293310,2006,A1 .Location in patent: Page/Page column 6

3
[ 153747-97-8 ]
[ 98-80-6 ]
[ 926646-63-1 ]

Reference： [1]Patent: WO2007/20888,2007,A1 .Location in patent: Page/Page column 46

4
[ 153747-97-8 ]
[ 1057681-96-5 ]

Yield	Reaction Conditions	Operation in experiment
35.9%	With n-butyllithium; In tetrahydrofuran; hexanes; at -78 - 20℃; for 1h;	The gaseous trifluororacetaldehyde was trapped with the dry ice-filled cold finger and dripped into a THF solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (1 g, 2.92 mmol) with 2.5 M n-butyllithium in hexanes (1.29 mL, 3.2 mmol) at -78 C under nitrogen atmosphere. After addition, the reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was quenched with saturated ammonium chloride aqueous solution at -78 0C and the mixture was partitioned <n="34"/>between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford a light yellow solid. The crude material was purified by flash chromatography on silica gel, eluting with 10 - 80% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford a colorless sticky solid (450 mg, 35.9% yield). The Boc protected titled compound (200 mg, 0.466 mmol) was stirred in 50% TFA in DCM (5 mL) for 10 min. The reaction mixture was concentrated to afford the titled product as a TFA salt (150 mg, yield 98%). MS (m/z, MH+): meas. 330.0 calc. 329.25

Reference： [1]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 32-33

5
[ 75-90-1 ]
[ 153747-97-8 ]
[ 1057681-90-9 ]

Yield	Reaction Conditions	Operation in experiment
42.6%		Triflurooacetaldehyde hydrate (1.7 g, 14.6 mmol) was added dropwise into a stirred mixture consisting of phosphorus pentoxide (I g, 7.3 mmol) and 4 mL of concentrated sulfuric acid at 95 0C. The freshly produced gaseous trifluororacetaldehyde was trapped with a dry ice-filled cold finger and dripped into a THF solution of tert-butyl 4-(5- bromopyridin-2-yl)piperazine-l-carboxylate (I g, 2.92 mmol) with 2.5 M n-butyllithium in hexanes (1.3 mL, 3.2 mmol) at -78 0C under nitrogen atmosphere. After addition, the reaction mixture was warmed to room temperature and stirred for 2 h. The mixture was quenched with saturated ammonium chloride aqueous solution at -78 0C and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford a brown solid. The crude material was purified by flash chromatography on silica gel, eluting with 10 - 80% EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford yellow sticky solid (450 mg, 42.6% yield). The Boc protected titled compound (380 mg, 1.1 mmol) was stirred in 20% TFA in DCM (5 mL) for 10 min. The reaction mixture was concentrated to afford the titled product as a TFA salt (260 mg, yield 95%). MS (m/z, MH+): meas. 262.2 calc. 262.25

Reference： [1]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 32

6
[ 6704-31-0 ]
[ 153747-97-8 ]
[ 1057682-01-5 ]

Yield	Reaction Conditions	Operation in experiment
32.7%		To a solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (250 mg, 0.73 mmol) in 3.5 mL anhydrous THF was added 1.6 M /j-butyllithium (500 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 min, the reaction mixture was charged with oxetan-3-one (131 mg, 1.82 mmol) in 200 muL DCM. The reaction mixture was stirred at -78 0C for 2 h and at room temperature for 16 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 - 100% EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford a off white solid (80 mg, 32.7% yield). The Boc protected title compound (140 mg, 0.417 mmol) was dissolved in DCM and charged with lutidine (194 muL, 1.67 mmol). The reaction mixture was cooled at 0 0C, charged with trimethylsilyl trifluoromethanesulfonate (1.25 mmol, 228 uL) and stirred at 0 0C for 2 h. The reaction mixture was poured into ice and the mixture was partitioned between DCM and water. The organic layer was dried over Na2SO4 and concentrated to afford a brown greasy solid (70 mg, yield 71%). MS (m/z, MH+): meas. 236.4 calc. 236.3

Reference： [1]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 33

7
[ 153747-97-8 ]
[ 1111-92-8 ]
[ 1057681-85-2 ]

Yield	Reaction Conditions	Operation in experiment
40.3%		To a solution of tert -butyl 4-(5-bromopyridin-2-yl)piperazine-l-carboxylate (250 mg, 0.730 mmol) in 2.5 mL anhydrous THF was added 2.5 M w-butyllithium (320 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 mins, the reaction mixture was charged with dimethyl phosphinic chloride (164.4 mg, 1.46 mmol) in 1 mL anhydrous THF. The reaction mixture was warmed to -30 0C over 3 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 - 100% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford an off white solid (100 mg, 40.3% yield). The Boc protected title compound was dissolved in 2-PrOH (1 mL) and charged with 4 N HCl. The reaction mixture was heated at 70 0C for 30 min, and concentrated to afford the titled product as a HCl salt. MS (m/z, MH+): meas. 240.2 calc. 240.3

Reference： [1]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 31

8
[ 504437-66-5 ]
[ 153747-97-8 ]
[ 1188335-25-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; N,N-dimethyl-formamide; toluene; at 90℃; for 1h;Inert atmosphere;	A mixture of tert- Butyl 4-(5-bromo-2-pyridinyl)-l-piperazinecarboxylate (0.203 g, 0.593 mmol) and7V-({(55)- 3-[3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-l,3-oxazolidin-5- yl}methyl)acetamide (0.270 g, 0.714 mmol) in dmf (4 niL), EtOH (1.5 niL), toluene (2.5 mL) and K2CO3 (1 mL, 2 M, 2 mmol) was purged with nitrogen. PdCl2(dppf) (24 mg, 0.03 mmol) was added and the mixture was heated to 900C under nitrogen for 1 h, then partitioned between EtOAc and water. Column chromatography (EtOAc) gave the titled compound (0.21O g, 69%) as a white solid. APCI MS m/z 514 (M + H). 1H NMR (400 MHz, DMSO-J6) delta 8.32 (bs, IH), 8.27 (t, J= 5.9 Hz, IH), 7.75 (ddd, J- 8.9, 2.4, 1.7 Hz, IH), 7.53-7.60 (m, 2H), 7.38 (dd, J- 8.6, 2.2 Hz, IH), 6.94 (d, J= 8.9 Hz, IH), 4.72-4.79 (m, IH), 4.15 (t, J= 9.1 Hz, IH), 3.77 (dd, J = 9.2, 6.5 Hz, IH), 3.52-3.57 (m, 4H), 3.40-3.46 (m, 6H), 1.84 (s, 3H), 1.43 (s, 9H).

Reference： [1]Patent: WO2009/120789,2009,A1 .Location in patent: Page/Page column 89

9
[ 1341208-52-3 ]
[ 153747-97-8 ]
[ 1341208-83-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7493 - 7502

10
potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
[ 153747-97-8 ]
[ 683274-61-5 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 2909 - 2911

11
[ 73183-34-3 ]
[ 153747-97-8 ]
[ 496786-98-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium acetate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	[0951] A solution ofcompound 90b (125 g, 366 mmol) inDMF (1.30 L)was treatedwith, 4,4,4',4',5,5,5',5'-octamethyl2,2'-bi(1,3,2-dioxaborolane) (186 g, 732 mmol), Pd(OAc) 2(4.09 g, 18.3 mmol), PPh3 (19.2 g, 73.2 mmol) and KOAc(108 g, 1.10 mol) under a nitrogen atmosphere. The resultingmixture was stirred overnight at 80° C. Upon cooling to roomtemperature, the solids were collected by filtration. The filtrate was concentratedunderreduced pressure, and the resultant residue was purified by flash colunm chromatography onsilica gel (EtOAc/petroleum ether (1 :50 v/v)) to obtain compound 90c as a white solid (80.0 g, 56percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H32BN3 0 4 : 390.2(M+H). found 390.2.
	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium acetate; XPhos; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere;	To a mixture of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate obtained in Reference Example 10 (800 mg), Pin2B2 (653 mg), X-Phos (224 mg), potassium acetate (688 mg) and Pd2 (dba)3.CHCl3 (124 mg) was added 1,4-dioxane (48 mL), and the interior of the vessel was purged with argon. The reaction mixture was stirred at 100° C. for an hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue were successively added 2-[(6-chloro-4-cyclopropylpyridin-2-yl)amino]pyridine-4-carbonitrile obtained in Reference Example 3 (422 mg), S-Phos (256 mg), potassium phosphate (995 mg), 1,4-dioxane (24 mL), water (1.2 mL) and palladium(II) acetate (70 mg), and the interior of the vessel was purged with argon. The reaction mixture was stirred at 100° C. for an hour. The reaction mixture was diluted with water, and extracted 3 times with ethyl acetate, the combined organic layers were washed with saturated brine, and dried over magnesium, sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was purified by column chromatography. To a suspension of the obtained solid in methanol (24 mL) was added 4 N hydrogen chloride-dioxane (12 mL), and the mixture was stirred at room, temperature for 1.5 hours. The solvent was evaporated under reduced pressure, and the obtained compound was washed with ethyl acetate to give 502 mg of the title compound as a yellow solid.
2.55 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 2h;Inert atmosphere;	Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (2.0 g, 5.84 mmol),Bis(boronic acid) pinacol ester (2.2 g, 8.77 mmol) andPotassium acetate (1.72 g, 17.53 mmol)To a solution of dimethyl sulfoxide (10 mL) was added Pd(dppf)Cl2.CH2Cl2 (473.0 mg, 0.58 mmol).The reaction was heated to 80°C and stirred for 2 hours.Cool toDiluted with ethyl acetate (100 mL) at room temperature and filtered through celite. The filtrate was washed with saturated brine (100 mL x 4), anhydrousSodium sulfate was dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 3/1) to give the title compoundThe product was an off-white solid (2.55 g, 112percent).

Reference： [1]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0945; 0950-0951
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 5361 - 5379
[3]Patent: US2013/225548,2013,A1 .Location in patent: Paragraph 0531; 0632
[4]Patent: CN104650049,2018,B .Location in patent: Paragraph 0426; 0427

12
[ 153747-97-8 ]
[ 1379522-33-4 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5361 - 5379

13
[ 153747-97-8 ]
[ 1211542-18-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5361 - 5379

14
[ 140-88-5 ]
[ 153747-97-8 ]
[ 1279027-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine;palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100℃; for 3h;	tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (800 mg) was dissolved in DMF (4 ml), and ethyl acrylate (368 mg), palladium(II) acetate (27 mg), tris(2-methylphenyl)phosphine (290 mg), and DIPEA (1.26 g) were added thereto, followed by stirring at 100 C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and then EtOAc was added thereto. The insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl 4-{5-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]pyridin-2-yl}piperazine-1-carboxylate (790 mg).

Reference： [1]Patent: US2012/184520,2012,A1 .Location in patent: Page/Page column 20

15
[ 766-11-0 ]
[ 57260-71-6 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
87.66%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 12h;	Step 1: K2CO3 (2.76 g, 20 mmol) was added into a mixture of 270-2 (1.76 g, 10 mmol) and 270-1 (2.24 g, 12 mmol) in DMF (20 mL). The mixture was stirred at 110C for 12h, poured into H2O (100 mL). The obtained mixture was extracted with EtOAc (150 mL×3). The organic phases were combined and washed with brines (150 mL), dried over anhydrous sodium sulfate, filtrated, and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=7:1) to deliver 270-3 (3 g, yield 87.66%) as colorless oil. MS ESI calcd for C14H2OBrN3O2 [M+H]+ 342, found 342.
	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 72h;	5-Bromo-2-fluoropyridine (3.0 g) was dissolved in DMF (18 ml), and K2CO3 (1.31 g) and tert-butyl piperazine-1-carboxylate (1.76 g) were added thereto, followed by stirring at 130 C. for 3 days. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (1.21 g).

Reference： [1]Patent: EP3124482,2017,A1 .Location in patent: Paragraph 0711; 0712
[2]Patent: US2012/184520,2012,A1 .Location in patent: Page/Page column 17

16
[ 153747-97-8 ]
[ 1374142-73-0 ]

Reference： [1]Patent: US2013/225548,2013,A1
[2]Patent: US2013/225548,2013,A1

17
[ 153747-97-8 ]
[ 1374146-04-9 ]

Reference： [1]Patent: US2013/225548,2013,A1

18
[ 153747-97-8 ]
[ 1374145-79-5 ]

Reference： [1]Patent: US2013/225548,2013,A1
[2]Patent: US2013/225548,2013,A1

19
[ 1041600-42-3 ]
[ 153747-97-8 ]
C₂₈H₃₅N₅O₆S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 495 - 506

20
[ 1082843-72-8 ]
[ 153747-97-8 ]
tert-butyl 4-(5-(6-amino-5-chloropyrazin-2-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 90℃;Inert atmosphere;	[0957] Into a 2 L 4-necked round-bottom flask, purged andmaintained with an inert atmosphere ofnitrogen, was placeda solution of compound 90e (42.8 g, 206 mmol) in 1,4-dioxane (1 L), compound 90b (80.0 g, 206 mmol), Pd(dppf)Cl2 (7.53 g, 10.3 mmol) andCs 2C0 3 (167 g, 514 mmol). Thereaction mixture was stirred overnight at 90 C. Upon cooling, the reaction was quenched with water (100 mL). Theresulting mixture was extracted with DCM. The combinedorganic layers were dried over Na2S04 , filtered and concentrated underreduced pressure. The resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (1 00:3 v/v)) to obtain compound 90fas a yellow solid(23.0 g, 29% yield). Mass Spectrum (LCMS, ESI pos.):Calcd. for C18H23ClN60 2 : 391.2 (M+H). found 391.1.

Reference： [1]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0945; 0956-0957

21
[ 24424-99-5 ]
[ 73406-97-0 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine; In dichloromethane; at 0 - 20℃;	[0949] To a solution ofcompound 90a (125 g, 516 mmol) inDCM (300mL), TEA (104 g, 1.03 mol) was added, followedby (BOC) 2 0 (135 g, 619 mmol) in portions with stirring at ooC. The resulting mixture was stirred overnight at room temperature. The reaction was then quenched with water (1 00mL), and the product was extracted with DCM (3x150 mL).The combined organic layers were concentrated underreduced pressure to obtain compound 90b as a white solid(125 g, 71% yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C14H20BrN3 0 2 : 342.1 (M+H). found 342.1.
	With sodium carbonate; In tetrahydrofuran; water; at 20℃; for 3h;	1-(5-bromopyridin-2-yl)piperazine (13.56 g, 56.01 mmol) and sodium carbonate (11.87 g, 112.01 mmol)Tetrahydrofuran/water (56 mL/56 mL)(Boc)2O (18 mL, 84.01 mmol) was added to the solution.The reaction was stirred at room temperature for 3 hours, filtered, and concentrated under reduced pressure.The residue was dispersed in ethyl acetate (100 mL) and saturated brine (100 mL).The separated organic phase was concentrated under reduced pressure to give a white solid (21.0 g, 110%).This product was used directly in the next step without purification.

Reference： [1]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0945; 0948-0949
[2]Patent: CN104650049,2018,B .Location in patent: Paragraph 0359; 0360

22
[ 53939-30-3 ]
[ 153747-97-8 ]

Reference： [1]Patent: US2014/364414,2014,A1

23
[ 153747-97-8 ]
tert-butyl 4-(5-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

24
[ 153747-97-8 ]
(E)-tert-butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

25
[ 153747-97-8 ]
tert-butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

26
[ 153747-97-8 ]
tert-butyl 4-(5-(8-morpholino-2-(quinoline-2-carboxamido)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

27
[ 153747-97-8 ]
N-(8-morpholino-5-(6-(piperazin-1-yl)pyridin-3-yl)imidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide hydrochloric acid salt [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

28
[ 153747-97-8 ]
tert-butyl 4-(5-(8-morpholino-2-(3-(quinolin-2-yl)azetidin-1-yl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

29
[ 153747-97-8 ]
2-((5-(6-(piperazin-1-yl)pyridin-3-yl)-8-(pyridin-4-yl)imidazo[1,2-a]pyrazin-2-yl)methoxy)quinoline trifluoroacetic acid salt [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1
[2]Patent: US2014/364414,2014,A1

30
[ 153747-97-8 ]
tert-butyl 4-(5-(6-amino-5-chloropyrazin-2-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

31
[ 153747-97-8 ]
ethyl 5-(6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyridin-3-yl)-8-chloroimidazo[1,2-a]pyrazine-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1
[2]Patent: US2014/364414,2014,A1

32
[ 153747-97-8 ]
tert-butyl 4-(5-(8-chloro-2-(hydroxymethyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1
[2]Patent: US2014/364414,2014,A1

33
[ 153747-97-8 ]
tert-butyl 4-(5-(2-(hydroxymethyl)-8-(pyridin-4-yl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1
[2]Patent: US2014/364414,2014,A1

34
[ 153747-97-8 ]
tert-butyl 4-(5-(8-(pyridin-4-yl)-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1
[2]Patent: US2014/364414,2014,A1

35
[ 153747-97-8 ]
tert-butyl 4-(5-(2-(hydroxymethyl)-8-(3-oxopiperazin-1-yl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1
[2]Patent: US2014/364414,2014,A1

36
[ 153747-97-8 ]
tert-butyl 4-(5-(2-chloro-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/364414,2014,A1

37
[ 180695-79-8 ]
[ 153747-97-8 ]
tert-butyl 4-(5-(1-(tert-butoxycarbonyl)piperidin-4-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1849 - 1853
Angew. Chem.,2016,vol. 128,p. 1881 - 1885,5

38
[ 39267-79-3 ]
[ 153747-97-8 ]
tert-butyl 4-(5-(oxetan-3-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1849 - 1853
Angew. Chem.,2016,vol. 128,p. 1881 - 1885,5

39
[ 3185-99-7 ]
[ 153747-97-8 ]
C₂₂H₂₉N₃O₄S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5636 - 5648

40
[ 1271-51-8 ]
[ 153747-97-8 ]
tert-butyl (R)-4-(5-(1-ferrocenylethyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 8372 - 8375

41
[ 73183-34-3 ]
[ 153747-97-8 ]
[ 919347-67-4 ]
[ 496786-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 20.25h;Inert atmosphere;	A mixture of 1-11 (4.30 g, 12.57 mmol) , bis (pinacolato) diboron (3.82 g 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100°C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL) , followed by extraction with ethyl acetate (50 mL x 3) . The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2SC> and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50percent EtOAc in hexanes to give the desired product Intermediate 1- XIII as a mixture of minor boronate ester together with major boronic acid . (4.8 g, crude yield 98percent) as a yellow solid; LCMS (for boronate ester) : m/z 390.2 [M+l]; LCMS (for boronic acid) : m/z 308.1 [M+l] .
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	Step II: tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (Intermediate 1-XIII) A mixture of 1-11 (4.30 g, 12.57 mmol), bis(pinacolato)diboron (3.82 g, 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100° C. for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (50 mL*3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50percent EtOAc in hexanes to give the desired product Intermediate 1-XIII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98percent) as a yellow solid; LCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M++1].
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	A mixture of 1?28 (4.30 g, 12.57 rnmol), bis(pinacolato)diboron (3.82 g, 15.07 mmcl) and KOAc (2.94 g, 37.69 mmcl) in 1,4?dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocenepalladium(II) dichloridedichloromethane complex (0.307 g, 0.376 mmcl), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100°C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate(50 mL x 3) . The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50percent EtOAc in hexanes to give the desired product Intermediate 1-CII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98percent) as a yellow solid; IJCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M+1].

Reference： [1]Patent: WO2015/88045,2015,A1 .Location in patent: Paragraph 0239
[2]Patent: US2017/8885,2017,A1 .Location in patent: Paragraph 0656; 0658
[3]Patent: WO2017/38909,2017,A1 .Location in patent: Paragraph 0308; 0309; 0311

42
[ 53939-30-3 ]
[ 57260-71-6 ]
[ 153747-97-8 ]

Yield	Reaction Conditions	Operation in experiment
81.5%	With potassium carbonate; In acetonitrile; at 110℃; for 12h;	General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7%).; The title compound was prepared using tert-butyl piperazine-1-carboxylate (1.45 g, 7.79 mmol),<strong>[53939-30-3]5-bromo-2-chloropyridine</strong> (1.00 g, 5.20 mmol) and potassium carbonate (1.44 g, 10.39 mmol) in acetonitrile (30 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (1.45 g, 8 1.5%).MS (ESI, pos. ion) m/z: 342.1 [M+H] and?H NMR (600 MHz, CDC13): (ppm) 8.17 (d, J 2.4 Hz, 1H), 7.52 (dd, J 9.0, 2.5 Hz, 1H), 6.52 (d, J 9.0 Hz, 1H), 3.55 - 3.49 (m, 4H), 3.49 - 3.45 (m, 4H), 1.46 (s, 9H).
58.8%	In N,N-dimethyl-formamide; at 80℃; for 14h;	To a stirred solution of 1-Boc piperazine (10.6 g, 57.29 mmol, Symax fine chemicals) in dryDMF (lOOmL), TEA (14.43 mL, 103.39 mmol) and 5-bromo-2-chloropyrimidine (10 g, 52.08mmol, Oakwood chemicals) were added and the reaction mixture was stirred at 80C for 14h. It was cooled down to rt and poured on iced water (100 mL). The resulting precipitatewas filtered and washed with hexane (50 mL) to afford the title compound. Yield: 58.8%(10 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 68.60(s, IH), 8.13 (dd, J= 8.6, 2.4Hz, IH), 7.54 (dd, J = 8.4, 0.4 Hz, IH), 3.22-3.20 (m, 4H), 2.61-2.59 (m, 4H), 1.42 (5, 9H).LCMS: (Method A) 343.9 (M +2H), Rt. 5.58 mm, 98.9% (Max).
58.8%	With triethylamine; In N,N-dimethyl-formamide; at 80℃; for 14h;	To a stirred solution of 1-Boc piperazine (10.6 g, 57.29 mmol, Symax fine chemicals) in dry DMF (100mL), TEA (14.43 mL, 103.39 mmol) and <strong>[53939-30-3]5-bromo-2-chloropyridine</strong> (10 g, 52.08 mmol, Oakwood chemicals) were added and the reaction mixture was stirred at 80C for 14 h. It was cooled down to rt and poured on iced water (100 mL). The resulting precipitate was filtered and washed with hexane (50 mL) to afford the title compound. Yield: 58.8% (10 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 8.60 (s, 1 H), 8.13 (dd, J = 8.6, 2.4 Hz, 1 H), 7.54 (dd, J = 8.4, 0.4 Hz, 1 H), 3.22-3.20 (m, 4H), 2.61 -2.59 (m, 4H), 1.42 (s, 9H). LCMS: (Method A) 343.9 (M +2H), Rt. 5.58 min, 98.9% (Max).

Reference： [1]Patent: WO2016/192657,2016,A1 .Location in patent: Page/Page column 65
[2]Patent: WO2017/144633,2017,A1 .Location in patent: Page/Page column 111
[3]Patent: WO2017/144639,2017,A1 .Location in patent: Page/Page column 96

43
[ 153747-97-8 ]
C₁₄H₂₀FN₃O₄S [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 1233 - 1237

44
[ 153747-97-8 ]
4-(3-(4-(5-isopropylpyridin-2-yl)-3-)-4-methoxyquinolin-8-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: EP3124482,2017,A1

45
[ 153747-97-8 ]
C₁₂H₁₉N₃ [ No CAS ]

Reference： [1]Patent: EP3124482,2017,A1

46
[ 153747-97-8 ]
C₁₇H₂₇N₃O₂ [ No CAS ]

Reference： [1]Patent: EP3124482,2017,A1

47
potassium isopropenyltrifluoroborane [ No CAS ]
[ 153747-97-8 ]
C₁₇H₂₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.32%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;Inert atmosphere;	Step 2: 270-3 (1.70 g, 4.97 mmol), Na2CO3 (1.05 g, 9.94 mmol) and potassium isopropenyl trifluoroborate (1.49 g, 9.94 mmol) were dissolved in DMF (2 mL), under nitrogen gas atmosphere, Pd(dppf)Cl2 (363.65 mg, 497 mumol) was added. The mixture was stirred at 70C for 2h, then poured into H2O (150 mL). The obtained mixture was extracted with EtOAc (150 mL×3). The organic phases were combined and washed with brines (150 mL), dried over anhydrous sodium sulfate, filtrated and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=10:1) to deliver 270-5 (1 g, yield 66.32%) as colorless oil. MS ESI calcd for C17H25N3O2 [M+H]+ 304, found 304.

Reference： [1]Patent: EP3124482,2017,A1 .Location in patent: Paragraph 0711; 0713

48
[ 75927-49-0 ]
[ 153747-97-8 ]
tert-butyl (E)-4-(5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

49
[ 153747-97-8 ]
1-(5-bromopyridin-2-yl)piperazine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.2%	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 4h;	To a stirred solution of <strong>[153747-97-8]tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate</strong> (10 g, 29.21 mmol) in 1,4-dioxane (5OmL), 4N HCI solution in dioxane (100 mL, IOV) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residuewas washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 6 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, IH), 7.82 (dd, J = 9.2, 2.4 Hz, IH), 6.99 (d, J = 9.2 Hz, IH), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 mm, 99.3 % (Max).
95.2%	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 4h;	To a stirred solution of <strong>[153747-97-8]tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate</strong> (10 g, 29.21 mmol) in 1,4-dioxane (50mL), 4N HCI solution in dioxane (100 mL, 10V) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residue was washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, 1 H), 7.82 (dd, J = 9.2, 2.4 Hz, 1 H), 6.99 (d, J = 9.2 Hz, 1 H), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 min, 99.3 % (Max).

Reference： [1]Patent: WO2017/144633,2017,A1 .Location in patent: Page/Page column 112
[2]Patent: WO2017/144639,2017,A1 .Location in patent: Page/Page column 97

50
[ 24367-66-6 ]
[ 153747-97-8 ]
C₁₉H₂₄N₄O₂ [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 4437 - 4442

51
[ 116008-37-8 ]
[ 153747-97-8 ]
C₁₉H₂₄N₄O₂ [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 4437 - 4442

52
(R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine [ No CAS ]
[ 153747-97-8 ]
tert-butyl (R)-4-(6'-((bis(tert-butoxycarbonyl))amino)-5'-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-[3,3'-bipyridin]-6-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,2-dimethoxyethane; water; at 100℃;Inert atmosphere;	The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, <strong>[153747-97-8]tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate</strong> (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

Reference： [1]Patent: CN104650049,2018,B .Location in patent: Paragraph 0976; 0977

53
(R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine [ No CAS ]
[ 153747-97-8 ]
(R)-5-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-6'-(piperazin-1-yl)-[3,3'-bipyridin]-6-amine [ No CAS ]

Reference： [1]Patent: CN104650049,2018,B

54
[ 766-11-0 ]
[ 153747-97-8 ]

Reference： [1]Patent: CN104650049,2018,B

55
[ 153747-97-8 ]
5-(1-(2,5-dichlorophenyl)ethoxy)-6'-(piperazin-1-yl)-3,3'-bipyridin-6-amine [ No CAS ]

Reference： [1]Patent: CN104650049,2018,B

56
[ 153747-97-8 ]
5-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-6'-(piperazin-1-yl)-[3,3'-bipyridine]-6-amine [ No CAS ]

Reference： [1]Patent: CN104650049,2018,B

57
[ 153747-97-8 ]
C₂₇H₃₀ClF₂N₅O₃ [ No CAS ]

Reference： [1]Patent: CN104650049,2018,B

58
[ 1613148-35-8 ]
[ 153747-97-8 ]
C₃₇H₄₇Cl₂N₅O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
250 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,2-dimethoxyethane; water; at 90℃;Inert atmosphere;	Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (202 mg, 0.59 mmol),N,N-bis(tert-butoxycarbonyl)-3-(1-(2,5-dichlorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3) ,2-Dioxaborolan-2-yl)pyridin-2-amine (300 mg, 0.49 mmol) andCesium carbonate (320mg, 0.98mmol)Ethylene glycol dimethyl ether/water (10 mL/1 mL)Pd(dppf)Cl2.CH2Cl2 (40 mg, 0.05 mmol) was added to the mixture.The reaction solution is heated to 90C.After stirring overnight, cool to room temperature and filter through celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 5/1) to give the title compound as a yellow oil (250 mg, 68%).

Reference： [1]Patent: CN104650049,2018,B .Location in patent: Paragraph 0362; 363

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Precautionary Statements-General
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Code	Phrase
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
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P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P401
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 153747-97-8 ]

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[ 153747-97-8 ] Synthesis Path-Upstream 1~9

[ 153747-97-8 ] Synthesis Path-Downstream 1~58

Related Functional Groups of [ 153747-97-8 ]

Bromides

Amides

Related Parent Nucleus of [ 153747-97-8 ]

Pyridines

Piperazines

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Inquiry

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[ 153747-97-8 ]

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[ 153747-97-8 ]