[ CAS No. 179110-74-8 ] {[proInfo.proName]}

Name: 179110-74-8|tert-Butyl piperidin-4-ylcarbamate hydrochloride|95%
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Quality Control of [ 179110-74-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 179110-74-8 ]

CAS No. :	179110-74-8	MDL No. :	MFCD03093509
Formula :	C₁₀H₂₁ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VVLJVJSHANVSGD-UHFFFAOYSA-N
M.W :	236.74	Pubchem ID :	2756028
Synonyms :

Calculated chemistry of [ 179110-74-8 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	66.27
TPSA :	50.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.85
Log Po/w (WLOGP) :	1.68
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.83
Consensus Log Po/w :	1.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.21
Solubility :	1.46 mg/ml ; 0.00618 mol/l
Class :	Soluble
Log S (Ali) :	-2.53
Solubility :	0.701 mg/ml ; 0.00296 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.05
Solubility :	2.13 mg/ml ; 0.00899 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Safety of [ 179110-74-8 ]

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

Application In Synthesis of [ 179110-74-8 ]

* 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 [ 179110-74-8 ]

[ 179110-74-8 ] Synthesis Path-Downstream 1~25

1
[ 179110-74-8 ]
[ 564-94-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl N-(piperidin-4-yl)carbamate hydrochloride; 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde With N-ethyl-N,N-diisopropylamine; trimethyl orthoformate In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	1 Intermediate 1; [1-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester PIPERIDIN-4-YL-CARBAMIC acid tert-butyl ester hydrochloride [CAS No. 73874-95- 0] (1. 63 g) was dissolved in DCM (20 ML) and DIISOPROPYLETHYLAMINE (1. 44 mi) and TRIMETHYLORTHOFORMATE (20 mi) were added. 6, 6-Dimethyl- bicyclo [3. 1.1] HEPT-2-ENE-2-CARBALDEHYDE [CAS No. 18486-69-6] (1. 26 mi) was added and the mixture stirred for 30 min, then sodium TRIACETOXYBOROHYDRIDE (1.8 g) was added and the mixture stirred overnight at room temperature. The solution was washed with sodium bicarbonate (20 ml), dried (MgS04), and evaporated to give a light yellow oil (2. 91 G). Purification by column chromatography on silica (5% MEOH/DCM) afforded the title compound as colourless solid (1. 75 g). Retention time 2. 25 minutes. M+H 335

Reference： [1]Current Patent Assignee: UCB - WO2004/94381, 2004, A1 Location in patent: Page 33-34

2
[ 73874-95-0 ]
[ 6038-12-6 ]
[ 342807-58-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl N-(piperidin-4-yl)carbamate hydrochloride; cyclooctene-1-carboxaldehyde With triethylamine; trimethyl orthoformate In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	Intermediate 1; 4- (BOC-AMINO)-1- (CYCLOOCTEN-1-VLMETHVL) PIPERIDINE Piperidin-4-ylcarbamic acid test-butyl ester hydrochloride [CAS No. 73874-95-0] (2 g) was dissolved in DCM (20 ML), and TEA (2 g) and TMOF (5 ML) were added. 1-CYCLOOCTENE carboxaldehyde [CAS No. 6038-12-6] (2 g) was added and the mixture was stirred for 30 min, then sodium triacetoxy- borohydride (4 g) was added and the mixture was stirred overnight at room temperature. The solution was washed with saturated NAHCO3 (20 ML), dried (MGS04) and evaporated to give the title compound as a beige solid (2.6 g). TLC Rf 0. 25 (5% MeOH/DCM).

Reference： [1]Current Patent Assignee: UCB - WO2005/3127, 2005, A1 Location in patent: Page 38

3
[ 179110-74-8 ]
[ 882562-41-6 ]
[ 882563-41-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium carbonate In N,N-dimethyl-formamide at 20 - 90℃; for 5h;	63 To a solution/suspension of Intermediate 3 (1.72 g) in dry DMF (75 ml) under nitrogen was added l-BOC-4-aminopiperidine hydrochloride (4.84 g) and Na2CO3 (4.35 g). The mixture was heated at 90°C for 5 hours. The mixture was cooled to room temperature and poured into water (800 ml) and the resulting solid was collected by filtration and dried in vacuo. Purification by column chromatography on silica eluting with 5% MeOH/DCM afforded the title compound as a yellow solid (1.23 g, 51%). LCMS 583 [M+H]+, RT 4.94 min. 1H NMR 300 MHz (CDCl3) 8.80 (1H, s), 8.65 (1H, d), 8.50 (1H, d), 8.30 (1H, s), 8.15 (1H, d), 7.35-7.20 (3H, m), 5.10 (1H, d), 4.20-3.90 (3H, m), 2.95 (2H, t), 2.40 (3H, s), 2.05 (2H, d), 1.55-1.35 (1 IH, m).

Reference： [1]Current Patent Assignee: UCB - WO2006/38001, 2006, A1 Location in patent: Page/Page column 70

4
[ 179110-74-8 ]
[ 710328-94-2 ]
[ 882563-44-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In N,N-dimethyl-formamide at 60℃; for 24h;	66 Alternatively, l-(2-chloropyrimidm-4-yl)-lH-benzimidazole (CAS 710328-94-2) (680 mg), l-BOC-4-aminoρiperidine.HCl (698 mg), TEA (1 ml) and DMF (10 ml) were combined under a nitrogen atmosphere and heated to 60°C for 24 hours. The solvents were removed in vacuo and the residue triturated with water to give the title compound as an off-white solid (1.4 g, 90%). Identical spectroscopic data.

Reference： [1]Current Patent Assignee: UCB - WO2006/38001, 2006, A1 Location in patent: Page/Page column 72

5
[ 179110-74-8 ]
[ 882562-56-3 ]
[ 882562-93-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine at 60℃; for 72h;	16 Intermediate 16 (150 mg), l-BOC-4-aminopiperidine.HCl (134 mg), DMF (5 ml) and TEA (0.087 ml) were combined and heated to 60°C for 72 hours. The reaction mixture was diluted with EtOAc (20 ml) and washed with water (2 x 20 ml). The organic layer was separated, concentrated in vacuo onto silica and purified by column chromatography to give the title compound as a white solid (115 mg, 50%). LCMS 373/375 [M-tBu]+, RT 3.90 min. 1H NMR 300 MHz (d6-DMSO) 8.75 (1H, s, br), 8.65 (1H, s, br), 8.00-7.85 (1H, m), 7.85-7.70 (2H, m), 7.45-7.30 (2H, m), 4.05-3.75 (3H, m), 2.95-2.7 (2H, m), 1.95-1.80 (2H, m), 1.50-1.30 (2H, m), 1.40 (9H, s).

Reference： [1]Current Patent Assignee: UCB - WO2006/38001, 2006, A1 Location in patent: Page/Page column 57

6
[ 882562-58-5 ]
[ 179110-74-8 ]
[ 882563-38-4 ]

Yield	Reaction Conditions	Operation in experiment
1%	Stage #1: 3-(2-chloropyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole; tert-butyl N-(piperidin-4-yl)carbamate hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 72h; Stage #2: With potassium hydroxide In methanol Heating / reflux;	60 To a solution of Intermediate 18 (600 mg) in dry DMF (10 ml) under nitrogen was added DEPEA (0.84 ml) and l-BOC-4-aminoρiperidine hydrochloride (573 mg). The reaction mixture was heated at 90°C for 3 days. The solvent was removed in vacuo and the residue dissolved in MeOH (40 ml) and to this added KOΗ (136 mg). The mixture was heated at reflux overnight. The solvent was removed in vacuo and the residue purified by prep ΗPLC (Method A) to afford the title compound as a cream solid (5 mg, 1%). LCMS 394 [M+Η]+, RT 2.43 min. 1H NMR SOO MHZ (d6-DMSO) 11.70 (1H, s, br), 8.60-8.50 (1H, m), 8.22 (1H, s), 8.13 (1H, d), 7.45 (1H, d), 7.21-7.10 (2H, m), 7.03 (1H, d), 6.93 (1H, d), 4.08-3.90 (2H, m), 3.86-3.75 (1H, m), 3.00-2.75 (2H, m), 2.04-1.87 (2H, m), 1.75-1.65 (1H, m), 1.40 and 1.38 (9H, 2 x s), 1.28-1.20 (1H, m).

Reference： [1]Current Patent Assignee: UCB - WO2006/38001, 2006, A1 Location in patent: Page/Page column 69

7
[ 882562-40-5 ]
[ 179110-74-8 ]
[ 882562-77-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 3-(2,5-dichloropyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole; tert-butyl N-(piperidin-4-yl)carbamate hydrochloride With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Stage #2: With potassium hydroxide In methanol at 20℃;	2 To a solution/suspension of Intermediate 2 (500 mg) in dry DMF (20 ml) under nitrogen was added l-BOC-4-aminopiperidine hydrochloride (1.5 g) and Na2CO3 (1.3 g). The mixture was heated at 120° C for 2 hours. The mixture was concentrated in vacuo and the residue dissolved in MeOH (40 ml). To this was added KOH (100 mg) and the mixture stirred at room temperature overnight. Water (30 ml) was added and the MeOH removed in vacuo. The residue was extracted with EtOAc (150 ml) and washed with brine (30 ml). The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography on silica eluting with 40% EtOAc/heptane afforded the title compound as a white solid (290 mg, 55%). TLC Rf 0.29 (40% EtOAc/heptane). LCMS 428/430 [M+H]+, RT 4.06 min. 1H NMR 300 MHz (d6-DMSO) 11.85 (1H, s, br), 8.60 (1H, s, br), 8.49 (1H, s), 8.27 (1H, s), 7.50 (1H, d), 7.30-7.14 (3H, m), 4.06-3.90 (3H, m), 3.00-2.77 (2H, m), 2.02-1.83 (2H, m), 1.50-1.32 (2H, m), 1.40 (9H, s).

Reference： [1]Current Patent Assignee: UCB - WO2006/38001, 2006, A1 Location in patent: Page/Page column 52

8
[ 179110-74-8 ]
[ 948038-77-5 ]
[ 948038-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl N-(piperidin-4-yl)carbamate hydrochloride; 3,4-dichloro-2-methyl-benzaldehyde With sodium tris(acetoxy)borohydride; acetic acid; triethylamine In tetrahydrofuran at 20℃; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran	8.b b) [l-(3,4-Dichloro-2-methyl-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl esterTo a stirred solution of triethylamine (0.13 mL) andpiperidin-4-yl-carbarnic acid tert-butyl ester hydrochloride (0.189 g) in tetrahydrofuran (1 mL) was added the product from part a) (0.179 g), sodium triacetoxyborohydride (0.302 g) and acetic acid (0.08 mL). The mixture was stirred overnight at room temperature, then partitioned between saturated sodium bicarbonate solution and dichloromethane. The aqueous phase was extracted with dichloromethane, the organics were combined, evaporated, and the residue was purified by flash chromatography (ethyl acetate / iso-hexane 1 :4) to give the subtitle compound (0.087 g).MS 373 / 375 [M + H]+ (APCI+)
	Stage #1: tert-butyl N-(piperidin-4-yl)carbamate hydrochloride; 3,4-dichloro-2-methyl-benzaldehyde With sodium tris(acetoxy)borohydride; acetic acid; triethylamine In tetrahydrofuran at 20℃; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran	3.b b) [l-(3,4-Dichloro-2-methyl-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester To a stirred solution of triethylamine (0.13 mL) and piperidin-4-yl-carbamic acid tert-butyl ester hydrochloride (0.189 g) in tetrahydrofuran (1 mL) was added the product from part a) (0.179 g), sodium triacetoxyborohydride (0.302 g) and acetic acid (0.08 mL). The mixture was stirred overnight at room temperature, then partitioned between saturated sodium bicarbonate solution and dichloromethane. The aqueous phase was extracted with dichloromethane, the organics were combined, evaporated, and the residue was purified by flash chromatography (ethyl acetate / iso-hexane 1 :4) to give the subtitle compound (0.087 g).MS 373 / 375 [M + H]+ (APCI+)

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2007/102767, 2007, A1 Location in patent: Page/Page column 28-29
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2007/102768, 2007, A1 Location in patent: Page/Page column 24-25

9
[ 249889-69-8 ]
[ 179110-74-8 ]
[ 530-62-1 ]
[ 394223-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; potassium carbonate In chloroform; water; N,N-dimethyl-formamide	400.b (b) (b) 4-tert-Butoxycarbonylamino-1-(6-methoxy-[1,5]naphthyridin-4-yl)aminocarbonylpiperidine To a solution of 4-amino-6-methoxy-[1,5]naphthyridine (Example 400a) (2.1 g, 13.5 mmol) and 4-(dimethylamino)pyridine (1.62 g) in anhydrous chloroform (45 ml) was added N,N-carbonyldiimidazole (3.28 g, 20.1 mmol). The mixture was stirred for 4 h at room temperature, then evaporated and the residue was dissolved in anhydrous DMF (45 ml). 4-tert-Butoxycarbonylaminopiperidine hydrochloride (3.34 g, 13.5 mmol) and potassium carbonate (1.89 g) were added, and the mixture was heated at 70° C. overnight. The mixture was evaporated and the residue was mixed with water (120 ml). The solid was filtered off and dried (3.89 g). MS (+ve ion electrospray) m/z 402 (MH+).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2004/38998, 2004, A1

10
[ CAS Unavailable ]
[ 179110-74-8 ]
[ 32315-10-9 ]
[ 651056-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl N-(piperidin-4-yl)carbamate hydrochloride; bis(trichloromethyl) carbonate With triethylamine In dichloromethane at 0℃; for 2h; Stage #2: piperidine With triethylamine In dichloromethane at 20℃; for 15h;	25 Reference Example 25 Reference Example 25 A suspension of 1.0 g of tert-butyl piperidin-4-ylcarbamate hydrochloride and 0.6 ml of triethylamine in 15 ml of methylene chloride was added to a solution of 418 mg of triphosgene in 10 ml of methylene chloride under cooling with ice-water bath. The reaction mixture was stirred for 2 hours with ice cooling, and then a solution of 358 mg of piperidine and 0.6 ml of triethylamine in 5 ml of methylene chloride was added thereto and stirred at room temperature for 15 hours. Aqueous 10 % citric acid solution was added to the reaction mixture, and this was extracted with EtOAc. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting solid was washed with ether to obtain 440 mg of tert-butyl [1-(piperidine-1-carbonyl)piperidin-4-yl]carbamate.

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - EP1541551, 2005, A1 Location in patent: Page/Page column 10-11

11
[ 882562-42-7 ]
[ 179110-74-8 ]
[ CAS Unavailable ]
[ 882562-81-4 ]

Yield	Reaction Conditions	Operation in experiment
11%	Stage #1: 3-(2-chloro-5-methylpyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole; tert-butyl N-(piperidin-4-yl)carbamate hydrochloride With sodium carbonate In N,N-dimethyl-formamide at 120℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 24h; Stage #3: ethyl isocyanate With sodium hydroxide; triethylamine more than 3 stages;	6 To a solution/suspension of Intermediate 4 (277 mg) in dry DMF (5 ml) under nitrogen was added l-BOC-4-aminopiperidine hydrochloride (855 mg) and Na2CO3 (765 mg). The mixture was heated at 12O°C overnight. After cooling to room temperature, the mixture was taken up in EtOAc (200 ml) and washed with water (3 x 100 ml) and saturated NaCl solution (100 ml). The organic layer was separated, dried over Na2SO4, filtered and the solvent removed in vacuo. The crude material was partially purified by EPO column chromatography on silica eluting with 60% EtO Ac/heptane. The resulting solid was dissolved in dry THF (10 ml) and to this was added 2N HCl (5 ml). The solution was stirred at room temperature for 24 hours. The pH of the mixture was adjusted to pH7 with 2N NaOH and extracted with DCM (4 x 75 ml). The organic layers were combined, washed with saturated NaCl solution (100 ml), separated, dried over Na2SO4, filtered and the solvent removed in vacuo. The crude material was partially purified by column chromatography on silica eluting with 80% EtOAc/heptane. The resulting solid (65 mg) was dissolved in DCE (2 ml) and to it was added TEA (20 μl) followed by ethyl isocyanate (11 μl). The mixture was stirred for 2 hours at room temperature, adsorbed onto silica and purified by column chromatography eluting with 5% MeOH/DCM to afford the title product as a white solid (41 mg, 11%). LCMS 519 [M+H]+, RT 3.31 min. 1H NMR 300 MHz (CDCl3) 8.25 (1H, s), 8.15 (1H, d), 8.05 (1H, d), 8.00-7.85 (3H, m), 7.55 (1H, d), 7.45 (2H, t), 7.40 (1H, t), 7.30 (1H, t), 5.00 (1H, d), 4.40 (1H, t), 4.15-4.00 (1H, m), 3.95 (2H, d), 3.25 (2H, dt), 3.00 (2H, t), 2.35 (3H, s), 2.10 (2H, d), 1.45 (2H, dq), 1.15 (3H, t).

Reference： [1]Current Patent Assignee: UCB - WO2006/38001, 2006, A1 Location in patent: Page/Page column 53-54

12
[ 73874-95-0 ]
[ 96-30-0 ]
2-(4-aminopiperidin-1-yl)-N-methylacetamide bis(hydrochloride) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		4-(BOC-amino)pirhoeridine hydrochloride (1.06 g) was partitioned between DCM (75 ml) and saturated aqueous Na2CO3 solution (75 ml). The aqueous layer was separated and extracted with DCM (50 ml). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo. The resulting white powder was dissolved in dry DMF (20 ml) under nitrogen and to this mixture was added Na2CO3 (617 mg) and 2- chloro-JV-methylacetamide (626 mg). The reaction mixture was stirred at room temperature for 24 hours. Water (80 ml) was added and the mixture was extracted with DCM (2 x 100 ml). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo. The residue was suspended in dry MeOH (10 ml) under nitrogen and to it was slowly added 2N HCl in Et2O (10 ml). The mixture was stirred at room temperature for 5 hours. The solvent was removed in vacuo and the residue was triturated in Et2O to afford the title compound as a white solid (1.2 g, 94%). LCMS 172 [M+H]+ (free base), RT 0.29 min. 1H NMR 300 MHz (d6-DMSO) 10.30-10.10 (1H, m, br), 8.80- 8.30 (4H, m, br), 4.00-3.70 (3H, m, br), 3.60-3.00 (4H, m), 2.55 (3H3 s, br), 2.20-1.80 (4H, m).

Reference： [1]Patent: WO2006/38001,2006,A1 .Location in patent: Page/Page column 47

13
[ 179110-74-8 ]
[ 1464153-70-5 ]
[ 1464153-71-6 ]

Yield	Reaction Conditions	Operation in experiment
70 mg	With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	29.2 Step 2: To a solution of 4-(3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2-fluorobenzoic acid (60 mg, 0.17 mmol) in DMF (3 mL), were successively added HATU (95 mg, 0.25 mmol), N-methylmorpholine (67 mg, 0.67 mmol) and tert-butyl piperidin-4-ylcarbamate hydrochloride (67 mg, 0.34 mmol). The reaction mixture was stirred at room temperature under inert atmosphere for 18 h, and then was diluted with water (10 mL) and the aqueous phase was extracted with DCM (3x 10 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent EtOAc) to afford 1 -(4-(3 -(4- cyanophenyl)imidazo[ 1 ,2-a]pyrazin-6-yl)-2-fluorobenzoyl)piperidin-4-ylcarbamate (70 mg, 76%) as an off-white powder. MS (ESI) m/z 441 [C25H2iFN60 + H]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2013/147711, 2013, A1 Location in patent: Page/Page column 108

14
[ 179110-74-8 ]
[ 1464153-75-0 ]
[ 1464153-78-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	31.2 Step 2: To a solution of 4-(3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2-chlorobenzoic acid (53 mg, 0.14 mmol) in DMF (3 mL) under inert atmosphere, was added HATU (80 mg, 0.21 mmol), JV-methyl morpholine (57 mg, 0.56 mmol) and tert-butyl piperidin-4- ylcarbamate hydrochloride (56 mg, 0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, then was diluted with water (10 mL) and extracted with DCM (3x10 mL). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, eluent EtOAc) to afford tert-butyl l-(4-(3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2- chlorobenzoyl)piperidin-4-ylcarbarnate (70 mg, 89%) as off-white powder. 1H NMR (400 MHz, CDC13) δ 9.26 (s, 1H), 8.61 (s, 1H), 8.23 (d, J= 2.7 Hz, 1H), 8.07-7.96 (m, 2H), 7.93- 7.81 (m, 4H), 7.35 (m, J= 9.8 Hz, 1H), 4.64 (s, 2H), 3.72 (s, lH), 3.44 (t, J= 12.5 Hz, 1H), 3.18 (t, J= 11.5 Hz, 1H), 3.00 - 2.94 (m, 3H), 2.08 (d, J= 10.6 Hz, lH), 1.93 (t, J= 10.3 Hz, 1H), 1.45 (s, 9H); MS (ESI) m/z 457 [C23H21C1N60 + H]+.
89%	With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	31.2 Example 31 To a solution of 4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-chlorobenzoic acid (53 mg, 0.14 mmol) in DMF (3 mL) under inert atmosphere, was added HATU (80 mg, 0.21 mmol), N-methyl morpholine (57 mg, 0.56 mmol) and tert-butyl piperidin-4-ylcarbamate hydrochloride (56 mg, 0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, eluent EtOAc) to afford tert-butyl 1-(4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-chlorobenzoyl)piperidin-4-ylcarbamate (70 mg, 89%) as off-white powder. 1H NMR (400 MHz, CDCl3) δ 9.26 (s, 1H), 8.61 (s, 1H), 8.23 (d, J=2.7 Hz, 1H), 8.07-7.96 (m, 2H), 7.93-7.81 (m, 4H), 7.35 (m, J=9.8 Hz, 1H), 4.64 (s, 2H), 3.72 (s, 1H), 3.44 (t, J=12.5 Hz, 1H), 3.18 (t, J=11.5 Hz, 1H), 3.00-2.94 (m, 3H), 2.08 (d, J=10.6 Hz, 1H), 1.93 (t, J=10.3 Hz, 1H), 1.45 (s, 9H); MS (ESI) m/z 457 [C23H21ClN6O+H]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2013/147711, 2013, A1 Location in patent: Page/Page column 110
[2]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - US2014/371199, 2014, A1 Location in patent: Paragraph 0431

15
[ 179110-74-8 ]
[ 1464153-68-1 ]
[ 1464153-69-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	27.3 Step 3:To a solution of 4-(3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2-methylbenzoic acid (50 mg, 0.14 mmol) in DMF (3 mL), were added HATU (80 mg, 0.21 mmol), N-methyl morpholine (57 mg, 0.56 mmol) and tert-butyl piperidin-4-ylcarbamate hydrochloride (56 mg, 0.30 mmol). The reaction mixture was stirred at room temperature under inert atmosphere for 18 h, then was diluted with water (10 mL) and extracted with DCM (3 <10 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, eluent EtO Ac) to afford tert-butyl l-(4-(3-(4-cyanophenyl)imidazo[l,2-a]pyrazin-6-yl)-2- methylbenzoyl)piperidin-4-ylcarbamate (63 mg, 83%) as off-white powder. MS (ESI) m/z 437 [C26H24N60 + H]+.
83%	With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	27.3 Example 27 To a solution of 4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-methylbenzoic acid (50 mg, 0.14 mmol) in DMF (3 mL), were added HATU (80 mg, 0.21 mmol), N-methyl morpholine (57 mg, 0.56 mmol) and tert-butyl piperidin-4-ylcarbamate hydrochloride (56 mg, 0.30 mmol). The reaction mixture was stirred at room temperature under inert atmosphere for 18 h, then was diluted with water (10 mL) and extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, eluent EtOAc) to afford tert-butyl 1-(4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-methylbenzoyl)piperidin-4-ylcarbamate (63 mg, 83%) as off-white powder. MS (ESI) m/z 437 [C26H24N6O+H]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2013/147711, 2013, A1 Location in patent: Page/Page column 106
[2]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - US2014/371199, 2014, A1 Location in patent: Paragraph 0417

16
[ 179110-74-8 ]
[ 79-04-9 ]
[ 2231279-64-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In dichloromethane at 20℃; for 5h;	XI.1.1 A mixture of tert-butyl N-(piperidin-4-yl)carbamate hydrochloride (2.50 g; 11.28 mmol), chloroacetylchloride (0.99 mL; 12.40 mmol) and TEA (3.29 mL; 23.68 mmol) in DCM (50 mL) is stirred for 5 h at r.t. The organic layer is extracted with water and hydrochloric acid (0.1 M). The organic layer is separated, dried and evaporated to dryness.Yield: 2.70 g (82% of theory) C12H20ClNO3 ESI Mass spectrum: m/z=262 [M+H]+

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2013/316981, 2013, A1 Location in patent: Paragraph 0344; 0345; 0346; 0347; 0348

17
[ 179110-74-8 ]
[ 1464153-70-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
70 mg	With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	29.2 Example 29 To a solution of 4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-fluorobenzoic acid (60 mg, 0.17 mmol) in DMF (3 mL), were successively added HATU (95 mg, 0.25 mmol), N-methylmorpholine (67 mg, 0.67 mmol) and tert-butyl piperidin-4-ylcarbamate hydrochloride (67 mg, 0.34 mmol). The reaction mixture was stirred at room temperature under inert atmosphere for 18 h, and then was diluted with water (10 mL) and the aqueous phase was extracted with DCM (3*10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent EtOAc) to afford 1-(4-(3-(4-cyanophenyl)imidazo[1,2-a]pyrazin-6-yl)-2-fluorobenzoyl)piperidin-4-ylcarbamate (70 mg, 76%) as an off-white powder. MS (ESI) m/z 441 [C25H21FN6O+H]+.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - US2014/371199, 2014, A1 Location in patent: Paragraph 0424

18
[ 179110-74-8 ]
[ 948038-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride; acetic acid; triethylamine / tetrahydrofuran / 20 °C 2: trifluoroacetic acid / dichloromethane / 20 °C 3: triethylamine / dichloromethane / 1 h / 0 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2007/102767, 2007, A1 Current Patent Assignee: ASTRAZENECA PLC - WO2007/102768, 2007, A1

19
[ 179110-74-8 ]
[ 948038-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid; triethylamine / tetrahydrofuran / 20 °C 2: trifluoroacetic acid / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2007/102767, 2007, A1 Current Patent Assignee: ASTRAZENECA PLC - WO2007/102768, 2007, A1

20
[ 851435-28-4 ]
[ 73874-95-0 ]
tert-butyl (1-(4-methyl-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidine-2-yl)piperidin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
700 mg	With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 3h; Microwave irradiation;	1.5 Step 5: (1-(4-methyl-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidine-2-yl)piperidin-4-yl)tert-butyl carbamate (1j) Dissolve compound 1h (500mg, 2.24mmol), compound 1i (800mg, 3.36mmol) and DIPEA (722mg, 5.6mmol) in NMP (5mL),Heat to 100 °C for 3h under microwave conditions. After the reaction, the reaction solution was cooled to room temperature, then poured into water (50 mL), and extracted with EA (50 mL).The organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain compound 1j (700 mg).

Reference： [1]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN111484479, 2020, A Location in patent: Paragraph 0410; 0411; 0424-0426

21
[ 179110-74-8 ]
[ 7006-50-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 80 °C

Reference： [1]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN111484479, 2020, A

22
[ 179110-74-8 ]
[ 2468230-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 80 °C 3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h 3.2: 1 h / 20 °C

Reference： [1]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN111484479, 2020, A

23
[ 179110-74-8 ]
[ 2468230-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 80 °C 3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h 3.2: 1 h / 20 °C 4.1: palladium on activated charcoal; hydrogen / methanol / 6 h / 15 - 30 °C

Reference： [1]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN111484479, 2020, A

24
[ 179110-74-8 ]
[ 2468229-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 80 °C 3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h 3.2: 1 h / 20 °C 4.1: palladium on activated charcoal; hydrogen / methanol / 6 h / 15 - 30 °C 5.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 3 h / 130 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN111484479, 2020, A

25
[ 73874-95-0 ]
[ 100-39-0 ]
[ 73889-19-7 ]

Yield	Reaction Conditions	Operation in experiment
555 mg	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	The free state of compound 1i (510.2 mg, 2.50 mmol) and TEA (773.34 mg, 7.49 mmol) were added to DCM (50 mL), BnBr (522.85 mg, 3.00 mmol) was slowly added at 0 C., and the mixture was stirred at room temperature for 3 h. After the reaction, the reaction solution was concentrated to dryness, and separated by silica gel column chromatography (PE:EA=20:1-5:1) to obtain the target product 18a (555mg)

Reference： [1]Patent: CN111484479,2020,A .Location in patent: Paragraph 0493-0497

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H230	May react explosively even in the absence of air
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H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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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
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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. 179110-74-8 ] {[proInfo.proName]}

Quality Control of [ 179110-74-8 ]

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Product Details of [ 179110-74-8 ]

Calculated chemistry of [ 179110-74-8 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 179110-74-8 ]

Application In Synthesis of [ 179110-74-8 ]

[ 179110-74-8 ] Synthesis Path-Downstream 1~25

Related Functional Groups of [ 179110-74-8 ]

Amides

Amines

Related Parent Nucleus of [ 179110-74-8 ]

Aliphatic Heterocycles

Piperidines

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Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 179110-74-8 ]

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[ 179110-74-8 ]