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[ CAS No. 87120-72-7 ]

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Chemical Structure| 87120-72-7

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CAS No. :	87120-72-7	MDL No. :	MFCD01076201
Formula :	C₁₀H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	200.28 g/mol	Pubchem ID :	1268291
Synonyms :

Safety of [ 87120-72-7 ]

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

Application In Synthesis of [ 87120-72-7 ]

Upstream synthesis route of [ 87120-72-7 ]
Downstream synthetic route of [ 87120-72-7 ]

[ 87120-72-7 ] Synthesis Path-Upstream 1~10

1
[ 87120-72-7 ]
[ 53786-28-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8895 - 8907

2
[ 87120-72-7 ]
[ 182223-54-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1021 - 1046
[2] Patent: WO2011/60321, 2011, A1,
[3] Patent: US2013/65925, 2013, A1,
[4] Patent: EP2757103, 2014, A1,
[5] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 26 - 41
[6] Patent: CN102250075, 2016, B,

3
[ 87120-72-7 ]
[ 127285-08-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 26 - 41

4
[ 917-61-3 ]
[ 87120-72-7 ]
[ 205058-11-3 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 17 h; Stage #2: With acetic acid In dichloromethane at 0 - 20℃; for 16 h;	tert-Butyl 4-(1,2-dihydro-2-oxo-5-phenylimidazol-3-yl)piperidine-1-carboxylate; tert-Butyl 4-(1,2-dihydro-2-oxo-5-phenylimidazol-3-yl)piperidine-1-carboxylate was synthesised as described in J. Med. Chem., 2005, 48, 5921. A solution of 2-bromo-1-phenylethanone (5 g, 25 mmol) in DCM (10 ml) was added dropwise to a stirred solution of tert-butyl 4-aminopiperidine-1-carboxylate (6 g, 30 mmol) and DⁱPEA (9.84 ml, 57.5 ml) in DCM (50 ml) over 1 hour, the reaction mixture was then stirred at room temperature for 16 hours. Sodium cyanate (3.41 g, 52.5 mmol) was added, the reaction mixture was then cooled to 0° C., the pH was brought to pH 4 with acetic acid and the reaction mixtures was stirred from 0° C. to RT over 16 hours. The reaction mixture was poured into water and extracted with DCM (3.x.). Organics combined, washed with water (3.x.), brine, dried (MgSO₄) and evaporated to dryness. The residue was triturated with ether, filtered and the solid was washed with ether to give a pale yellow solid (4.04 g, 47percent). LC/MS (10percent to 99percent): M/Z (M+H)⁺ (obs)=344; t_R=3.01.

Reference： [1] Patent: US2008/4261, 2008, A1, . Location in patent: Page/Page column 137

5
[ 2142-69-0 ]
[ 917-61-3 ]
[ 87120-72-7 ]
[ 205058-11-3 ]

Reference： [1] Patent: US2018/50992, 2018, A1, . Location in patent: Paragraph 1388

6
[ 917-61-3 ]
[ 87120-72-7 ]
[ 70-11-1 ]
[ 205058-11-3 ]

Reference： [1] Patent: US6344/449, 2002, B1, . Location in patent: Example A1a)
[2] Patent: US6344449, 2002, B1, . Location in patent: Example A1a)

7
[ 87120-72-7 ]
[ 124-63-0 ]
[ 287953-38-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With pyridine In pyridine at 20℃; for 16 h; Cooling with ice	5.00 g (25.0 mmol) of BOC-4-aminopiperidine are dissolved in pyridine (19.8 mL) and cooled in an ice bath. 2.13 mL (27.5 mmol) of methanesulfonyl chloride are added slowly. The reaction is stirred at RT for 16 h. After diluting with water, the reaction is extracted with DCM. Organic layers are washed with water, dried with MgSO₄ and filtered. The solvent is removed under reduced pressure to afford 6.30 g of (1-Methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester. Yield: 91percent; ESI-MS: 279 [M+H]⁺

Reference： [1] Patent: US8865744, 2014, B1, . Location in patent: Page/Page column 25; 26

8
[ 87120-72-7 ]
[ 950649-10-2 ]

Reference： [1] Patent: WO2007/106705, 2007, A1,

9
[ 87120-72-7 ]
[ 1174020-64-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 780 - 785
[2] Patent: WO2015/33191, 2015, A1,
[3] Patent: US10085999, 2018, B1,

10
[ 87120-72-7 ]
[ 1048970-17-7 ]

Reference： [1] Journal of the American Chemical Society, 2018, vol. 140, # 34, p. 10700 - 10704

[ 87120-72-7 ] Synthesis Path-Downstream 1~25

1
[ 500-22-1 ]
[ 67589-90-6 ]
[ 87120-72-7 ]
[ 127406-55-7 ]
4-pentyl-cyclohexanecarboxylic acid (4-pyridin-3-yl-benzyl)-(1-pyridin-3-ylmethyl-piperidin-4-yl)-amide [ No CAS ]

Reference： [1]Molecules,2003,vol. 8,p. 556 - 564

2
[ 67589-90-6 ]
[ 87120-72-7 ]
[ 123-08-0 ]
[ 127406-55-7 ]
4-pentyl-cyclohexanecarboxylic acid [1-(4-hydroxy-benzyl)-piperidin-4-yl]-(4-pyridin-3-yl-benzyl)-amide [ No CAS ]

Reference： [1]Molecules,2003,vol. 8,p. 556 - 564

3
[ 67589-90-6 ]
[ 87120-72-7 ]
[ 590-86-3 ]
[ 127406-55-7 ]
4-pentyl-cyclohexanecarboxylic acid [1-(3-methyl-butyl)-piperidin-4-yl]-(4-pyridin-3-yl-benzyl)-amide [ No CAS ]

Reference： [1]Molecules,2003,vol. 8,p. 556 - 564

4
[ 149849-94-5 ]
[ 87120-72-7 ]
[ 951004-16-3 ]

Yield	Reaction Conditions	Operation in experiment
34%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 110℃; for 0.666667h;microwave irradiation;	Step 2: 2-(1-tert-Butoxycarbonyl-piperidin-4-ylamino)-pyrimidine-4-carboxylic acid methyl ester A mixture of <strong>[149849-94-5]2-chloro-pyrimidine-4-carboxylic acid methyl ester</strong> (0.62 g, 3.59 mmol, 1.0 equiv), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.86 g, 4.31 mmol, 1.2 equiv; commercially available) and N-ethyl diisopropylamine (0.73 mL, 0.56 g, 4.31 mmol, 1.2 equiv) in acetonitrile (60 mL) was heated by microwave irradiation to 110 C. After stirring for 40 min, the reaction mixture was concentrated under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluding with a gradient of heptane/ethyl acetate providing 0.48 g (34%) of the title compound. MS (ISP): 337.5 [M+H]+.

Reference： [1]Patent: US2007/225271,2007,A1 .Location in patent: Page/Page column 33

5
[ 87120-72-7 ]
[ 144163-97-3 ]
C₂₄H₃₆N₆O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		Example AC; Example AC was prepared following the procedures for steps I-III (Scheme 20) for Example Z, with the exception that tert-butyl 4-amino-l- piperidinecarboxylate was used instead of tert-butyl 2-aminoethylcarbamate (Compound 62). After Combiflash purification, 60 mg (44%) of Example AC was obtained, m/z: 537.1 (M+H)+. 1H NMR (CDCk) delta 8.82 (s, IH); 7.87 (s, IH); 6.97 (s, IH); 5.82 (br s, IH); 5.30 (m, 3H); 4.80-4.40 (m, 5H); 4.03 (m, IH); 3.72 (br s, IH); 3.34 (m, IH); 3.18 (m, IH); 3.01 (s, 3H); 2.79 (m, IH); 2.20-1.90 (m, 4H); 1.40 (d, /=7 Hz, 6H); 0.97, 0.90 (d, /=7 Hz, 6H).

Reference： [1]Patent: WO2008/10921,2008,A2 .Location in patent: Page/Page column 226; 228

6
[ 38696-20-7 ]
[ 87120-72-7 ]
[ 1187635-09-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium phosphate; copper(l) iodide; N,N-diethylsalicylamide; In N,N-dimethyl-formamide; at 90℃; for 24h;	Step 2: 4-(Pyrimidin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester A mixture of <strong>[38696-20-7]5-bromo-2-phenyl-pyrimidine</strong> (3.50 g, 14.89 mmol, 1.0 equiv), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (4.48 g, 22.33 mmol, 1.5 equiv), copper(I) iodide (0.28 g, 1.49 mmol, 0.1 equiv), N,N-diethylsalicylamide (0.58 g, 2.98 mmol, 0.2 equiv) and K3PO4 (3.16 g, 14.89 mmol, 1.0 equiv) in degassed DMF (30 mL) was heated under Ar to 90° C. for 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from water (300 mL) and 25percent NH4OH (30 mL) with ethyl acetate (3*300 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluding with a gradient of heptane/ethyl acetate (4:1-->1:1) to provide 1.98 g (38percent) of the title compound. MS (ESI): 377.1 [M+Na]+.

Reference： [1]Patent: US2008/64697,2008,A1 .Location in patent: Page/Page column 27

7
[ 87120-72-7 ]
[ 104146-17-0 ]
[ 866329-16-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 18h;	Add sodium triacetoxyborohydride (30. 50 g, 144 mmol) to a stirred solution of 4- amino-1-N Boc-piperidine (18.00 g, 89.9 mmol), <strong>[104146-17-0]4-chloro-thiazole-5-carbaldehyde</strong> (13.09 g, 88.7 mmol), acetic acid (5.5 mL, 96.1 mmol), and 1, 2-dichloroethane (350 mL). Stir the reaction for 18 hours at room temperature under nitrogen. Pour the reaction into 2N NaOH (400 mL) and extract with ethyl acetate (3 X 150 mL). Wash the ethyl acetate with brine (2 X 150 mL). Dry the ethyl acetate over sodium sulfate and then filter off the sodium sulfate. Concentrate on a rotary evaporator and purify the crude product by flash chromatography on silica gel eluting with 75percent ethyl acetate/hexanes then with 100 percent ethyl acetate to yield 21.78 g (74percent) of 4-f [ (4-chloro-thiazol-5-yl) methyl]-amino}- piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z = 332.1 (M+1) ; IH NMR (CDC13) : 8 = 8.67 (s, 1H), 4.10-4. 02 (m, 4H), 2.88-2. 82 (m, 2H), 2.74- 2.67 (m, 1H), 1.92-1. 89 (m, 2H), 1.49 (s, 9H), 1.37-1. 28 (m, 3H).

Reference： [1]Patent: WO2005/92885,2005,A1 .Location in patent: Page/Page column 94

8
[ 87120-72-7 ]
[ 5334-40-7 ]
[ 844443-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20℃;	4-Nitropyrazole-3-carboxylic acid (7.3 g; 15.9 mmol) was added to a stirred solution of 4-amino-1-Boc- piperidine (10.2 mg; 51 mmol), EDC (10.7 g; 55.8 mmol), and HOAt (55.8 g; 19.1 mmol) in DMF (100 ml), and then stirred at room temperature overnight. The solvent was removed by evaporation under reduced pressure and the residue triturated with water (250ml). The resultant cream solid was collected by filtration, washed with water then dried under vacuum to give 13.05 g of 4-[(4-nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1- carboxylic acid tert-butyl ester (LC/MS: Rt 2.50, [M+H]+ 340).
	With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20℃;	4-Nitropyrazole-3-carboxylic acid (7.3 g; 15.9 mmol) was added to a stirred solution of 4-amino-1-Boc- piperidine (10.2 mg; 51 mmol), EDC (10.7 g; 55.8 mmol), and HOAt (55.8 g; 19.1 mmol) in DMF (100 ml), and then stirred at room temperature overnight. The solvent was removed by evaporation under reduced pressure and the residue triturated with water (250ml). The resultant cream solid was collected by filtration, washed with water then dried under vacuum to give 13.05 g of 4-[(4-nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1- carboxylic acid tert-butyl ester (LC/MS: Rt 2.50, [M+H]+ 340).
		Add 6.31 kg of raw material to a 100 L reactor, N,N-dimethylformamide (45 L), carbodiimide (6.59 kg), 1-hydroxybenzotriazole (4.65 kg), stirred for 0.5 h, The ice water bath was cooled to 0 to 10 C, and the starting material 1 (4.5 kg) was added in portions, and then the temperature was raised to 20-25 C, and the reaction was stirred for 16 hours. The reaction solution was added to 270 L of water, and a solid was precipitated, suction filtered, washed, and separated, and the organic phases were combined and dried

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4986 - 4999
[2]Patent: WO2006/77424,2006,A1 .Location in patent: Page/Page column 184
[3]Patent: WO2006/77428,2006,A1 .Location in patent: Page/Page column 161-162
[4]Patent: CN109705090,2019,A .Location in patent: Paragraph 0106-0109

9
[ 79-37-8 ]
[ 87120-72-7 ]
[ 5334-40-7 ]
[ 844443-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; water;	Step 1: Synthesis of 4-[(4-nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester 4-Nitropyrazole-3-carboxylic acid (20.0 g, 127.4 mmol) was suspended in CH2Cl2/DMF (99:1, 400 mL), treated cautiously with oxalyl chloride (11.6 mL, 134 mmol) and then stirred at room temperature for 16 h. The reaction mixture was evaporated then re-evaporated with toluene (*3) to give a yellow solid. The resultant acid chloride was suspended in dioxane (400 mL), treated with triethylamine (26.4 mL, 190 mmol) followed by 4-amino-1-BOC-piperidine (25.0 g, 125 mmol) and stirred at room temperature for 6 h. The reaction mixture was filtered and the solid collected stirred in water (500 mL) and then re-filtered. The solid collected was dried in vacuo, azeotroping with toluene, to give the title compound (37.6 g).

Reference： [1]Patent: US2010/21420,2010,A1

10
[ 60230-36-6 ]
[ 87120-72-7 ]
[ 1298899-50-9 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 1048 - 1055

11
[ 383-29-9 ]
[ 87120-72-7 ]
[ 1247029-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 100 - 120℃;	Example 31. Preparation of 4-[4-(4-fluoro-benzenesulfonyl)- phenylamino]-piperidine-l-carboxylic acid tert-buty ester intermediate.A solution of 4-amino-piperidine-l-carboxylic acid tert-butyl ester (427 mg; 2.13 mmol), bis (4 -fluorophenyl) sulfone (493 mg; 1.94 mmol) and potassium carbonate (1.01 g; 7.76 mmol) in dimethylsulfoxide (5 mL) is heated over night at 1000C. The temperature is then increased to 1200C and the mixture is reacted at this temperature for 24 hours. The reaction is then diluted with dichloromethane (100 mL), filtered and the filtrate is washed with aq. IN hydrochloric acid (2 x 20 mL), and water (2 x 20 mL). The organic layer is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane methanol 100:0 (200 mL) and then 98:2 (150 mL)) to afford the desired product (653 mg; 1.50 mmol)

Reference： [1]Patent: WO2010/115688,2010,A1 .Location in patent: Page/Page column 141-142

12
[ 3222-49-9 ]
[ 87120-72-7 ]
[ 916344-56-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4521 - 4525

13
[ 87120-72-7 ]
[ 2435-50-9 ]
[ 1293396-29-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	In tert-butyl methyl ether; for 2.5h;	tert-Butyl 4-[(1E)-pyrimidin-4-ylmethylene]amino}piperidine-1-carboxylate (C13) Pyrimidine-4-carbaldehyde (C12) (23.00 g, 212.8 mmol) was added to a mixture of tert-butyl 4-aminopiperidine-1-carboxylate (42.61 g, 212.8 mmol) in tert-butyl methyl ether (1.52 L). After 2.5 hours, the reaction was filtered, and the filtrate was concentrated in vacuo to provide an amber oil, which was generally taken directly to the following step. Yield: 56.30 g, 193.9 mmol, 91%. 1H NMR (400 MHz, CDCl3) partial spectrum, characteristic peaks: delta 1.49 (s, 9H), 7.95 (dd, J=5.2, 1.5 Hz, 1H), 8.36 (s, 1H), 8.81 (d, J=5.2 Hz, 1H), 9.28 (d, J=1.5 Hz, 1H).

Reference： [1]Patent: US2011/98272,2011,A1 .Location in patent: Page/Page column 23

14
[ 1570-05-4 ]
[ 87120-72-7 ]
[ 1446498-72-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	With dmap; benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	<strong>[1570-05-4]3,4-bis(benzyloxy)benzoic acid</strong> (12) (50.0 mg, 0.14 mmol) was dissolved in dry DMF (2 mL), and then treated with 4-amino-1-Boc-piperidine (34.0 mg, 0.17 mmol), HOBT (22.9 mg, 0.17 mmol), EDC (0.030 mL, 0.17 mmol), TEA (0.058 mL, 0.42 mmol), and DMAP (1.2 mg, 0.01 mmol). The reaction mixture was stirred at room temperature for 16 h under an argon atmosphere and the solvent was removed. The crude compound was purified by column chromatography on silica gel using hexane/AcOEt 40:60 as eluent. Yield 55percent. Mp 158?160 °C. 1H NMR (CDCl3), (delta) 1.46?1.58 (m, 2H), 1.50 (s, 9H, CH3), 1.94?1.99 (d, 2H, CH2, J = 10.63), 2.82?2.94 (t, 2H, J = 11.91), 4.02?4.08 (d, 3H, J = 11.90), 5.18 (s, 4H, CH2O) 5.78?5.82 (br s, NH), 6.86?7.46 (m, 13H, ArH). 13C NMR (CDCl3), 166.2, 154.7, 151.6, 148.7, 136.8, 136.6, 128.6, 128.0, 127.6, 127.5, 127.2, 119.9, 114.0, 113.6, 79.7, 71.3, 71.0, 47.2, 42.7, 32.2,28.5; Anal. C31H36N2O5 (C, H, N). HPLC-GS 100percent. MS m/z 517 (M+1).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4575 - 4580

15
[ 31680-07-6 ]
[ 87120-72-7 ]
[ 1598418-32-6 ]

Yield	Reaction Conditions	Operation in experiment
0.37 g		To a stirred solution of 4-amino-piperidine-l-carboxylic acid tert -butyl ester (0.3g,1.8mmol) and <strong>[31680-07-6]4-methyl-3-nitro-benzaldehyde</strong> (0.363g, 1.8mmol) in ethanol (6ml) was added titanium isopropoxide (0.3ml) at 0C and stirred. The reaction was gradually brought to RT and stirred for 16h. Then sodium borohydride (0.068g,l .8mmol) was added followed by catalytic amount of acetic acid and stirred for 3h at ambient temperature. Upon completion, the solvents in the reaction were distilled out. The crude was diluted with 10%MeOH-CH2Cl2 solution and washed with water. The organic layer was then dried over sodium sulfate and concentrated under reduced pressure. The obtained crude was taken was purified by (100-200mesh) silicagel column chromatography eluting the required compound with 80% EtOAc-Petether as a off-white solid (0.370g).

Reference： [1]Patent: WO2014/57415,2014,A2 .Location in patent: Page/Page column 40

16
[ 27613-36-1 ]
[ 87120-72-7 ]
[ 1598418-21-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of 4-amino-piperidine-l-carboxylic acid tert -butyl ester (0.35g, 1.75mmol) and <strong>[27613-36-1]5-formyl-2-methyl-benzonitrile</strong> (0.327g, 1.97mmol) in ethanol(6ml) was added titanium isopropoxide (0.35ml) at 0°C and stirred. The reaction is gradually brought to RT and stirred for 16h. Then sodium borohydride (0.078g, 1.97mmol) was added followed by catalytic amount of acetic acid and stirred for 3h at ambient temperature. Upon completion, the solvents in the reaction were distilled out. The crude was diluted with 10percent MeOH-CI^C solution and washed with water. The organic layer was then dried over Sodium sulfate and concentrated under reduced pressure. The obtained crude was purified by (100-200mesh) silicagel column chromatography to afford the required compound.

Reference： [1]Patent: WO2014/57415,2014,A2 .Location in patent: Page/Page column 67-68

17
[ 31169-27-4 ]
[ 87120-72-7 ]
C₁₆H₂₁BrN₄O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4281 - 4285

18
[ 25171-19-1 ]
[ 87120-72-7 ]
C₁₉H₂₅ClN₄O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2315 - 2325

19
[ 5093-70-9 ]
[ 87120-72-7 ]
tert-butyl 4-[(2,6-dimethylpyridin-4-yl)amino]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 100℃;Inert atmosphere; Schlenk technique;	A Schlenk tube was charged with tert-butyl 4-aminopiperidine-1-carboxylate (0.249 g,1.24 mmol), <strong>[5093-70-9]4-bromo-2,6-dimethylpyridine</strong> (0.193 g, 1.04 mmol), potassium tertbutoxide (0.290 g, 2.58 mmol) and toluene (5 mL). The Schlenk tube was subjected tothree cycles of evacuation-backfilling with argon and then tris(dibenzylideneacetone) dipalladium (76 mg, 0.08 mmol) and 2-dicyclohexylphosphino-2?,4?,6?-triisopropyl biphenyl (10 mg, 0.02 mmol) were added. After three further cycles of evacuation-backfilling with argon, the Schienk tube was sealed and the mixture was stirred overnight at 100 °C. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth Celite® and the filtrate was concentrated to dryness. The crude residue was purified by reverse phase chromatography (gradientfrom water to methanol) to yield the title compound (188 mg, 60percent). LRMS (mlz): 306 (M+1).1H-NMR (300 MHz, CDCI3): 1.34 (td, 2H), 1.47 (s, 9H), 2.01 (dd, 2H), 2.39 (s, 6H), 2.93 (t, 2H), 3.39-3.54 (m, 1H), 3.92 (d, 1H), 4.06 (d, 2H), 6.15 (s, 2H).

Reference： [1]Patent: WO2015/86693,2015,A1 .Location in patent: Page/Page column 80; 81

20
[ 3314-30-5 ]
[ 87120-72-7 ]
C₁₈H₂₆N₄O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3148 - 3152

21
[ 1538-08-5 ]
[ 87120-72-7 ]
[ 4637-24-5 ]
tert-butyl 4-(3-(trifluoromethyl)-4H-1,2,4-triazol-4-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1534 - 1554

22
[ 87120-72-7 ]
[ 1048970-17-7 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 10700 - 10704
[2]Chemistry - A European Journal,2018,vol. 24,p. 17210 - 17214
[3]Angewandte Chemie - International Edition,2019,vol. 58,p. 8572 - 8576
Angew. Chem.,2019,vol. 131,p. 8660 - 8664,5

23
[ 87120-72-7 ]
[ 950649-10-2 ]

Reference： [1]Patent: WO2007/106705,2007,A1

24
[ 87120-72-7 ]
[ 59786-31-1 ]
methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.49%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃;Inert atmosphere;	Example 68 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(piperidin-4-ylamino)isonicotinamide Compound 118a. To a stirred solution of <strong>[59786-31-1]methyl 3-bromoisonicotinate</strong> (0.500 gm, 2.3148 mmol, 1 equiv) & tert-butyl 4-aminopiperidine-1-carboxylate (0.463 gm, 2.3148 mmol, 1 equiv) and CS2CO3 (1.5 gm, 4.6296 mmol, 2 equiv) in dioxane (15 mL). The resulting mixture was purged with nitrogen for 10 min followed by addition of Pd2(dba)3 (0.106 gm, 0.1157 mmol, 0.05 equiv) and xantphos (0.134 gm, 0.2314 mmol, 0.1 equiv), again purged with nitrogen for 10 min. The reaction mixture was heated at 120 C. for overnight. The progress of reaction was monitored by LCMS. The reaction mixture was diluted with water (30 mL), extracted with EtOAc (2*50 mL). The combined organic layers were washed with water (30 mL), with brine (30 mL), dried over Na2SO4, concentrated to afford the crude which was purified by flash chromatography to obtain methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinate (400 mg, 51.49%) as a white solid. LCMS: 336.3 [M+H]+ 1H NMR: (400 MHz, DMSO-d6) delta 8.41 (s, 1H), 7.60-7.51 (m, 2H), 7.27 (d, J=7.9 Hz, 1H), 3.00 (m., 4H), 2.04-1.88 (s, 3H), 1.44-1.35 (s, 9H), 1.31-1.12 (m, 4H).

Reference： [1]Patent: US2019/185451,2019,A1 .Location in patent: Paragraph 0966-0969

25
[ 448906-60-3 ]
[ 87120-72-7 ]
tert-butyl 4-[[2-(hydroxymethyl)-6-methyl-4-pyridyl]amino]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72 mg	With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2?,4?,6?-triisopropyl-1,1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; caesium carbonate; In 1,4-dioxane; at 100℃; for 2h;Microwave irradiation; Inert atmosphere;	To a flask was added <strong>[448906-60-3](4-bromo-6-methyl-2-pyridyl)methanol</strong> (compound 5a, CAS: 448906-60-3, Vendor: BePharm, 150 mg, 742 m mol), tert-butyl 4-aminopiperidine-1-carboxylate (compound 5b, CAS: 87120-72-7, Vendor: BePharm, 223 mg, 1.11 mmol), CS2CO3 (726 mg, 2.23 mmol) and 1,4-dioxane (5 mL), the suspension was bubbled with N2 for 5 mins and BrettPhos Pd-G3 (20 mg, 22 m mol) was added. The mixture was heated to 100 C under microwave for 2 hrs. After being cooled down, the mixture was diluted with 10 mL EA and filtered through celite, the filtrate was concentrated to give a brown oil, which was purified by flash column (MeOH/DCM = 0 to 15%) to give compound 5c (72 mg) as a yellow oil. MS: calc'd 322 (MH+), measured 322 (MH+).

Reference： [1]Patent: WO2019/238629,2019,A1 .Location in patent: Page/Page column 29-30

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P321
P322
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P401
P402	Store in a dry place.
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Disposal
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Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H240	Heating may cause an explosion
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Health hazards
Code	Phrase
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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
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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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