[ CAS No. 7149-42-0 ]

Name: 7149-42-0|(1-Methylpiperidin-4-yl)methanamine|97%
Brand: Ambeed
SKU: A123245
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 7149-42-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 7149-42-0 ]

Product Details of [ 7149-42-0 ]

CAS No. :	7149-42-0	MDL No. :	MFCD05022430
Formula :	C₇H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AGTPSAZJSOQXHJ-UHFFFAOYSA-N
M.W :	128.22	Pubchem ID :	81574
Synonyms :

Calculated chemistry of [ 7149-42-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.17
TPSA :	29.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	0.07
Log Po/w (WLOGP) :	-0.09
Log Po/w (MLOGP) :	0.57
Log Po/w (SILICOS-IT) :	0.55
Consensus Log Po/w :	0.58

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.61
Solubility :	31.3 mg/ml ; 0.244 mol/l
Class :	Very soluble
Log S (Ali) :	-0.24
Solubility :	74.1 mg/ml ; 0.578 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.77
Solubility :	21.9 mg/ml ; 0.171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.03

Safety of [ 7149-42-0 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P370+P378-P403+P235	UN#:	2733
Hazard Statements:	H226-H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 7149-42-0 ]

* 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 [ 7149-42-0 ]
Downstream synthetic route of [ 7149-42-0 ]

[ 7149-42-0 ] Synthesis Path-Upstream 1~3

1
[ 62718-28-9 ]
[ 7149-42-0 ]

Yield	Reaction Conditions	Operation in experiment
11%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 66℃; for 25.5 h;	1-METHYLISONIPECOTAMIDE (6.75g, 47. 5MMOLES) (PREPARED as described in Preparative Example 245, Step A above) was dissolved in anhydrous THF (350mL) and the resulting mixture was added in portions to a stirred slurry of lithium aluminum hydride (1.8g, 47. 5mmoles) in anhydrous THF (100ML) at 0 C under nitrogen. The mixture was stirred at 0 C for 30min and then heated at 66 C for 25h under nitrogen. Distilled water (1.88mL) was added dropwise to the stirred mixture at 0 C, followed by 20percent aqueous sodium hydroxide (1.42mL) and then distilled water (6.75mL) and the mixture was stirred for 15min. The mixture was filtered and the solids were washed with THF and dichloromethane. The combined filtrates were evaporated to dryness and chromatographed on a silica gel column (30x5cm) using 15percent-20percent (10percent CONC. ammonium hydroxide in METHANOL)-DICHLOROMETHANE as the eluant to give 4-(aminomethyl)-1- methylpiperidine (0.678g, 11percent) : FABMS: m/z 129.1 (MH+) ; HRFABMS: m/z 129.1389 (MH+). Calcd. FOR C7HL7N2 : m/z 129.1392 ; aH (d6-DMSO) : 2.08ppm (3H, S,-NCH3) ; 8C (D6-DMSO) : CH3: under DMSO peaks; CH2: 29.6, 29.6, 46.7, 55.2, 55.2 ; CH: 46.2.

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
[2] Patent: WO2004/22561, 2004, A1, . Location in patent: Page 110-11

2
[ 20691-92-3 ]
[ 7149-42-0 ]

Reference： [1] Yakugaku Zasshi, 1956, vol. 76, p. 968[2] Chem.Abstr., 1957, p. 2771

3
[ 7149-42-0 ]
[ 928337-00-2 ]
[ 1025065-69-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium t-butanolate In toluene for 12 h; Heating / reflux	12. Scheme for the Synthesis of 7-29 . Scheme 613. Synthesis of N-((1-methylpiperidin-4-yl)methyl)-3-(3-(trifluoromethoxy) phenyl imidazofi ,2-blpyridazin-6-amine (Compound 7-29):[0148] To the toluene (5 mL) solvent was added 7-12 (40 mg, 0.128 mmol), (1-methylpiperidin-4-yl)methanamine (24.53 0.191 mmol), ligand (7.53 mg, 0.019 mmol), Pd₂(dba)₃ (8.76, 9.56 mmol) and NaOfBu (17.40 mg, 0.181 mmol). The resulting reaction mixture was degassed for 10 min under argon and then was heated to reflux overnight (12 h). The crude product was EPO <DP n="58"/>concentration and preparative TLC was performed with 10percent MeOH/DCM solvent system afforded 17.6 mg of 7-23 (50percent).

Reference： [1] Patent: WO2008/58126, 2008, A2, . Location in patent: Page/Page column 54-55

[ 7149-42-0 ] Synthesis Path-Downstream 1~69

1
[ 7149-42-0 ]
[ 88-10-8 ]
[ 105906-90-9 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 968
Chem.Abstr.,1957,p. 2771

2
[ 7149-42-0 ]
[ 79-44-7 ]
[ 103985-92-8 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 968
Chem.Abstr.,1957,p. 2771

3
[ 7149-42-0 ]
[ 59943-32-7 ]
[ 71318-26-8 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1981,vol. 31,p. 279 - 288

4
[ 7149-42-0 ]
[ 356068-93-4 ]
5-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1<i>H</i>-pyrrole-3-carboxylic acid (1-methyl-piperidin-4-ylmethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1116 - 1119

5
[ 62718-28-9 ]
[ 7149-42-0 ]

Yield	Reaction Conditions	Operation in experiment
11%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 66℃; for 25.5h;	1-METHYLISONIPECOTAMIDE (6.75g, 47. 5MMOLES) (PREPARED as described in Preparative Example 245, Step A above) was dissolved in anhydrous THF (350mL) and the resulting mixture was added in portions to a stirred slurry of lithium aluminum hydride (1.8g, 47. 5mmoles) in anhydrous THF (100ML) at 0 C under nitrogen. The mixture was stirred at 0 C for 30min and then heated at 66 C for 25h under nitrogen. Distilled water (1.88mL) was added dropwise to the stirred mixture at 0 C, followed by 20% aqueous sodium hydroxide (1.42mL) and then distilled water (6.75mL) and the mixture was stirred for 15min. The mixture was filtered and the solids were washed with THF and dichloromethane. The combined filtrates were evaporated to dryness and chromatographed on a silica gel column (30x5cm) using 15%-20% (10% CONC. ammonium hydroxide in METHANOL)-DICHLOROMETHANE as the eluant to give 4-(aminomethyl)-1- methylpiperidine (0.678g, 11%) : FABMS: m/z 129.1 (MH+) ; HRFABMS: m/z 129.1389 (MH+). Calcd. FOR C7HL7N2 : m/z 129.1392 ; aH (d6-DMSO) : 2.08ppm (3H, S,-NCH3) ; 8C (D6-DMSO) : CH3: under DMSO peaks; CH2: 29.6, 29.6, 46.7, 55.2, 55.2 ; CH: 46.2.

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1116 - 1119
[2]Patent: WO2004/22561,2004,A1 .Location in patent: Page 110-11

6
[ 639091-33-1 ]
[ 7149-42-0 ]
6-[4-(3-fluoro-benzyloxy)-phenoxy]-<i>N</i>-(1-methyl-piperidin-4-ylmethyl)-nicotinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5039 - 5056

7
[ 7149-42-0 ]
[ 952300-54-8 ]
C₂₃H₂₅ClN₆OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In ethanol; at 70 - 80℃; for 16h;Product distribution / selectivity;	Synthesis of Example 154 20.15 mg (0.050 mmol) of the intermediate compound (XI.2) and 22.77 mg (0.225 mmol) triethylamine are placed in 1 ml of ethanol, 9.62 mg (0.075 mmol) (1-methyl-piperidin-4-yl)-methylamine in 1 ml of ethanol are added. The reaction mixture is stirred for 16 hours at 70 C. Then it is evaporated down, the residue is purified by chromatography (LCMS). Corresponding fractions are lyophilised. Yield: 24.80 mg (85% of theoretical)

Reference： [1]Patent: US2007/238746,2007,A1 .Location in patent: Page/Page column 32; 48; 56

8
[ 39546-32-2 ]
[ 7149-42-0 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1116 - 1119

9
[ 7149-42-0 ]
1-[4-({4-[(1-methyl-piperidin-4-ylmethyl)-amino]-butylamino}-methyl)-piperidin-1-yl]-2-naphthalen-1-yl-ethanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1261 - 1264

10
[ 7149-42-0 ]
[ 1493-27-2 ]
[ 600725-10-8 ]

Yield	Reaction Conditions	Operation in experiment
86%		[0407] The product was obtained analogously to intermediate product 15 starting from <strong>[7149-42-0]C-(1-methyl-piperidin-4-yl)-methylamine</strong> and 1-fluoro-2-nitro-benzene. [0408] Yield: 86% of theory [0409] Rf=0.09 (Alox, dichloromethane/MeOH/conc. aqueous ammonia 90/10/1 v/v/v) [0410] ESI-MS: (M+H)+=220

Reference： [1]Patent: US2003/236282,2003,A1 .Location in patent: Page 20

Yield	Reaction Conditions	Operation in experiment
61%		The residue was purified by vacuum distillation to give the title compound (1.56 g). Yield=61%. b.p. 30-50 C. (4 mmHg) 1 H NMR(CDCl3) delta 1.28-1.32(m, 2H), 1.42-1.56(m, 1H), 1.77(d, J=13 Hz, 2H), 2.03(dt, J=2 Hz,10 Hz, 2H), 2.29(s, 3H), 2.68(d, J=7 Hz, 2H), 2.91(d, J=12 Hz, 2H)
11%		B. 4-(AMINOMETHYL)-1-METHYLPIPERIDINE 1-Methylisonipecotamide (6.75 g, 47.5 mmoles) (prepared as described in Preparative Example 245, Step A above) was dissolved in anhydrous THF (350 mL) and the resulting mixture was added in portions to a stirred slurry of lithium aluminum hydride (1.8 g, 47.5 mmoles) in anhydrous THF (100 mL) at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 min and then heated at 66 C. for 25 h under nitrogen. Distilled water (1.88 mL) was added dropwise to the stirred mixture at 0 C., followed by 20% aqueous sodium hydroxide (1.42 mL) and then distilled water (6.75 mL) and the mixture was stirred for 15 min. The mixture was filtered and the solids were washed with THF and dichloromethane. The combined filtrates were evaporated to dryness and chromatographed on a silica gel column (30*5 cm) using 15%-20% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give 4-(aminomethyl)-1-methylpiperidine (0.678 g, 11%): FABMS: m/z 129.1 (MH+); HRFABMS: m/z 129.1389 (MH+). Calcd. for C7H17N2: m/z 129.1392; deltaH (d6-DMSO): 2.08 ppm (3H, s, -NCH3); delta C (d6-DMSO): CH3: under DMSO peaks; CH2: 29.6, 29.6,46.7, 55.2, 55.2; CH: 46.2.

Yield	Reaction Conditions	Operation in experiment
		C. Dissolve the product of part B above in 10 ml of anhydrous tetrahydrofuran (THF), cool to 0 C. and add dropwise to 10 ml of 1 M borane dissolved in THF at 0 C. Stir for 8 hours at 0 C. and add 5 ml of 12N HCl. Reflux for 1 hour. Evaporate the solvent to a dry residue and add 50 ml of methanol. Evaporate to obtain the product 1-methyl-4-aminomethylpiperidine, as the dihydrochloride salt. Substitute the product of part C above in the reaction scheme described in Example I to obtain the title compound.

13
[ 7149-42-0 ]
C₁₄H₇ClN₄OS [ No CAS ]
C₂₁H₂₃ClN₆OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine; In ethanol; at 70℃; for 16h;	18.84 mg (0.050 mmol) of the intermediate compound (XII.7) and 22.77 mg (0.225 mmol) triethylamine are placed in 1 ml of ethanol, 9.62 mg (0.075 mmol) (1-methyl-piperidin-4-yl)-methylamine in 1 ml of ethanol are added. The reaction mixture is stirred for 16 hours at 70 C. Then the mixture is evaporated down, the residue is purified by chromatography (LCMS). Corresponding fractions are lyophilised. Yield: 15.70 mg (56% of theoretical)

Reference： [1]Patent: US2007/238730,2007,A1 .Location in patent: Page/Page column 30

14
[ 7149-42-0 ]
[ 928337-00-2 ]
[ 1025065-69-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In toluene; for 12h;Heating / reflux;	12. Scheme for the Synthesis of 7-29 . Scheme 613. Synthesis of N-((1-methylpiperidin-4-yl)methyl)-3-(3-(trifluoromethoxy) phenyl imidazofi ,2-blpyridazin-6-amine (Compound 7-29):[0148] To the toluene (5 mL) solvent was added 7-12 (40 mg, 0.128 mmol), (1-methylpiperidin-4-yl)methanamine (24.53 0.191 mmol), ligand (7.53 mg, 0.019 mmol), Pd2(dba)3 (8.76, 9.56 mmol) and NaOfBu (17.40 mg, 0.181 mmol). The resulting reaction mixture was degassed for 10 min under argon and then was heated to reflux overnight (12 h). The crude product was EPO <DP n="58"/>concentration and preparative TLC was performed with 10% MeOH/DCM solvent system afforded 17.6 mg of 7-23 (50%).

Reference： [1]Patent: WO2008/58126,2008,A2 .Location in patent: Page/Page column 54-55

15
[ 7149-42-0 ]
[ 1025066-18-5 ]
[ 1025065-77-3 ]

Yield	Reaction Conditions	Operation in experiment
7.26%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In toluene; at 150℃; for 1h;Microwave irradiation;	7-Methyl-N-((1-methylpipehdin-4-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)- imidazo [1 ,2-blpyridazin-6-amine (Compound 7-37): EPO <DP n="74"/>[0196] To the toluene (5ml_) solvent was added Compound 11 (57 mg, 0.174mmol), (1-methylpiperidine-4-yl)methanamine 17 (26.8 mg, 0.209 mmol), ligand (10.27 mg, 0.026 mmol), NaOtBu (23.40 mg, 0.244 mmol) and Pd2(dba)3 (11.95, 0.013 mmol). The resulting reaction mixture was degassed for 10 min under argon and then was heated with microwave at 150 0C for 1h. Concentration and preparative TLC (10% MeOH/DCM) afforded 5.3 mg (7.26%) of Compound 7-37.[0197] 1H-NMR (300MHz, CD3OD) 8.35 (s, 1 H), 8.01 (d, J=8.4Hz, 1 H), 7.83(s, 1 H), 7.51(t, J=7.8Hz, 2H), 7.21(d, J=8.1 Hz, 2H), 3.65(m, 2H), 2.36(m, 3H), 2.98(d, J=11.4Hz, 2H), 2.48(m, 2H), 2.26(d, J=0.9Hz, 3H), 2.24(s, 3H), 1.91(m, 4H), 1.32(m, 1 H).. 19F-NMR (300Hz, CD3OD) -56.456, FTMS+p MALDI: 420.20113 (M+H)+, Theory Exact Mass: 420.20112.

Reference： [1]Patent: WO2008/58126,2008,A2 .Location in patent: Page/Page column 70-71

16
[ 7149-42-0 ]
[ 1089672-86-5 ]
[ 1089672-70-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5541 - 5544

17
[ 7149-42-0 ]
[ 1001065-84-4 ]
[ 1080623-27-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7855 - 7865

18
[ 7149-42-0 ]
5-chloro-3-((5-(6-chloropyrazin-2-yl)furan-2-yl)methylene)indolin-2-one [ No CAS ]
5-chloro-3-((5-(6-((1-methylpiperidin-4-yl)methylamino)pyrazin-2-yl)furan-2-yl)methylene)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; at 140℃; for 0.25h;microwave irradiation;	Example 47 Synthesis of 5-chloro-3-((5-(6-((1-methylpiperidin-4-yl)methylamino)pyrazin-2-yl)furan-2-yl)methylene)indolin-2-one A solution of 5-chloro-3-((5-(6-chloropyrazin-2-yl)furan-2-yl)methylene)indolin-2-one (80 mg, 0.224 mmol), <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (32 mg, 0.246 mmol), and triethylamine (0.035 ml, 0.246 mmol) in dioxane (0.4 mL) was prepared in a microwave tube. The reaction mixture was microwaved at 140 C. for 15 minutes. The solution was diluted with water, and the precipitate was collected by filtration to yield the desired (70 mg). The precipitate was further purified by prep TLC eluding with 2% MeOH in dichloromethane. LCMS (ES): m/z 450 [M+1]+.

Reference： [1]Patent: US2010/41635,2010,A1 .Location in patent: Page/Page column 117

19
[ 7149-42-0 ]
[ 1041466-54-9 ]
[ 1041466-76-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4196 - 4200

20
[ 7149-42-0 ]
[ 73178-79-7 ]
[ 1236121-44-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3540 - 3544

21
[ 7149-42-0 ]
[ 1256913-15-1 ]
[ 1256913-13-9 ]

Yield	Reaction Conditions	Operation in experiment
> 99%		6-bromo-l-('('l-methylpiperidin-4-yl)methyl)-4-oxo-1.4-dihvdro-1.8-naphthyridine-3- carboxylateTo a solution of ethyl 2-(5-bromo-2-fluoronicotinoyl)-3-(dimethylamino)acrylate (Intermediate 3, 784 mg, 2.27 mmol) dissolved in THF (12 mL) was added (1- methylpiperidin-4-yl)methanamine (291 mg, 2.27 mmol). The reaction mixture was stirred at 60 0C for 2 h, then cooled to room temperature, concentrated under reduced pressure, and the resulting residue was resuspended in DMF (12 mL). Potassium carbonate was added (942 mg, 6.81 mmol, 3 equiv.) to the suspension, and the reaction was stirred at 70 0C for 18 h. The reaction mixture was cooled to room temperature then quenched with 1 N HCl. The reaction mixture was partitioned between water (15 mL) and dichloromethane (15 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 15 mL), and the combined organic layers were concentrated to provide ethyl 6-bromo-l-((l- methylpiperidin-4-yl)methyl)-4-oxo-l,4-dihydro-l,8-naphthyridine-3 -carboxylate (945 mg, >;99 %). Calcd for Ci8H22BrN3O3 [M + H]+: 409.9.

Reference： [1]Patent: WO2010/136817,2010,A1 .Location in patent: Page/Page column 106

22
[ 7149-42-0 ]
[ 1226789-23-6 ]
[ 1266620-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃;Inert atmosphere; Microwave irradiation; Sealed tube; Heating;	General procedure: To a solution containing S.I.-1 (0.20 g, 0.81 mmol) in 2 mL EtOH in a microwave reaction vial which could be sealed with a Teflon cap was added 4-amino-2,2,6,6-tetramethylpiperidine (0.13 g, 0.81 mmol). The tube was briefly flushed with an Argon stream (approximately 30 s) and sealed. The reaction was heated to 150 C for 1 hr in microwave and then allowed to cool to room temperature and stand for 12 hours, during which time a glassy solid formed. The solid was collected by filtration, washed with cold hexanes, and dried to give 140 mg (48%) of the product as a colorless crystalline solid.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 91 - 101

23
[ 7149-42-0 ]
[ 1202704-54-8 ]
[ 1202700-61-5 ]

Yield	Reaction Conditions	Operation in experiment
35.3%		l-(l-Methyl-4-piperidinyl)methanamine (41 mg, .316 mmol) was added to a solution of methyl l-[(2-chlorophenyl)methyl]-5-([2-(ethyloxy)-2-oxoethyl]amino}carbonyl)-2,4-dihydroxy- 6-oxo- l,6-dihydro-3-pyridinecarboxylate (prepared by following the procedure of example Id, 160 mg, .360 mmol) in chloroform (3 ml). The solution solidified upon standing. The mixture was heated in a microwave (1500C, 30 min). The solution was washed with IN HCl (2ml). The organic layer was concentrated in-vacuo and the residue dissolved in ethanol (6 ml) and treated with 6N <n="80"/>NaOH. The mixture was stirred at rt over night. Upon completion of the saponification the solution was diluted with ethyl acetate (20 ml) and washed with IN HCl (7 ml). The organic layer was concentrated in-vacuo and the residue was dissolved in dimethyl sulfoxide (1.5 ml) and purified by HPLC (0.1% TFA, acetonitrile, 0.1% TFA water) to yield the title compound as a white solid. Yield: 29 mg, 15.5%, MS (ES+): [M+H]+ = 507.1, 1H NMR (400 MHz, OMSO-d6) delta ppm 1.38 (q, J=12.63 Hz, 2 H), 1.84 (d, J=I 1.87 Hz, 3 H), 2.73 (s, 3 H), 2.89 (d, J=7.07 Hz, 2 H), 3.30 (t, J=5.81 Hz, 2 H), 3.42 (d, J=11.87 Hz, 2 H), 4.08 (d, J=5.31 Hz, 2 H), 5.15 (s, 2 H), 6.89 (d, J=7.07 Hz, 1 H), 7.19 - 7.34 (m, J=7.52, 7.23, 7.09, 7.09, 1.64 Hz, 2 H), 7.49 (dd, J=7.45, 1.64 Hz, 1 H), 9.35 (br. s., 1 H), 9.69 (br. s., 1 H), 9.85 (br. s., 1 H), 13.02 (br. s., 1 H)

Reference： [1]Patent: WO2009/158315,2009,A1 .Location in patent: Page/Page column 78; 79

24
[ 7149-42-0 ]
[ 64-18-6 ]
[ 1313733-36-6 ]
(1-methyl-piperidin-4-ylmethyl)-[3-(3-trifIuoromethoxy-phenyl)-7,8-dihydro-6,9-dioxa-1,2,3a,4-tetraaza-cyclopenta[a]naphthalen-5-yl]-amine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt = 2.92, 3.01 min, [M+H]+ m/z 465.0.1H NMR (300 MHz, DMSO-d6) S 8.54 (s, 1 H), 8.40 (d, J = 8.0 Hz, 1 H), 8.26 (s, 1 H), 7.69 (m, 1 H), 7.50 (d, J = 8.3 Hz, 1 H), 7.23 (t, J = 5.7 Hz, 1H), 4.55 (m, 4H), 3.22 (m, 2H), 2.77 (d, J = 1 1.3 Hz, 2H), 2.14 (s, 3H), 1.84 (m, 3H), 1.70 (m, 2H), 1.23 (m, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 107

25
[ 7149-42-0 ]
[ 64-18-6 ]
[ 1313733-38-8 ]
[8,9-dimethyl-3-(3-trifluoromethoxy-phenyl)-8,9-dihydro-7H-6-oxa-1,2,3a,4,9-pentaaza-cyclopenta[a]naphthalen-5-yl]-(1-methyl-piperidin-4-ylmethyl)-amine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt = 3.34, 3.45 min, [M+H]+ m/z 492.3.1H NMR (300 MHz, DMSO-d6) delta 8.59 (s, 1 H), 8.42 (d, J = 8.0 Hz, 1 H), 8.23 (s,1 H), 7.68 (m, 1H), 7.48 (d, J = 8.3 Hz, 1 H), 6.76 (t, J = 5.8 Hz, 1 H), 4.23 (dd, J =10.6, 2.6 Hz, 1H), 4.09 (dd, J = 10.6, 2.0 Hz, 1 H), 3.60 (m, 4H), 3.19 (m, 2H),2.84 (m, 2H), 2.21 (s, 3H), 1.96 (m, 2H), 1.74 (m, 3H), 1.24 (m, 5H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 105

26
[ 7149-42-0 ]
[ 64-18-6 ]
[ 1313733-43-5 ]
[6,8-dimethyl-3-(3-trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1,2,3a,4,6-pentaaza-cyclopenta[a]naphthalen-5-yl]-(1-methyl-piperidin-4-ylmethyl)-amine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 1 ): Rt = 3.28 min, [M+H]+ m/z 492.1. NMR (300 MHz, DMSO-d6) delta 8.58 (s, 1 H), 8.43 (d, J = 7.9 Hz, 1 H), 8.20 (s, 1 H), 7.69 (m, 1 H), 7.49 (m, 1 H), 6.91 (s, 1H), 4.46 (m, 1 H), 3.20 (m, 4H), 2.80 (m, 2H), 2.70 (s, 3H), 2.17 (s, 3H), 1.89 (m, 3H), 1.72 (m, 2H), 1.46 (d, J = 6.2 Hz, 3H), 1.25 (m, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 106

27
[ 7149-42-0 ]
[ 1313733-30-0 ]
[ 1313732-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers.Example 1t3-(4- ethoxy-phenyl)-6-methyl-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza- cyclopenta[a]naphthalen-5- -(1-methyl-piperidin-4-ylmethyl)-amineAmine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 3): Rt = 3.59 min, [M+H]+ = 424.1.H NMR (300 MHz, MeOD) delta 8.34 (d, J = 8.4, 2H), 7.10 (d, J = 8.4, 2H), 4.50 (s, 2H), 3.90 (s, 3H), 3.42 (d, J = 6.1 , 3H), 2.75 (d, J = 19.5, 8H), 2.17 (s, 1 H), 2.04 (d, J = 13.5, 2H), 1 .57 (s, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87

28
[ 7149-42-0 ]
[ 1313733-32-2 ]
[ 1313732-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methanamineHPLC-MS (method 1 ): Rt=3.333 min, [M+H]+m/z 478.3.1H NMR (300 MHz, CDCI3) delta 8.55 (s, 1 H), 8.40 (d, J = 8.0, 1 H), 7.51 (t, J = 8.1 , 1 H), 7.27 (d, J = 8.1 , 1 H), 5.22 (t, J = 5.7, 1 H), 4.38 - 4.25 (m, 2H), 3.70 (s, 3H), 3.49 (dd, J = 13.5, 9.3, 4H), 3.37 (t, J = 6.3, 2H), 2.69 (s, 3H), 2.65 (s, 1 H), 2.13 (s, 1 H), 1.95 (s, 1 H), 1.78 (t, J = 12.2, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 95

29
[ 7149-42-0 ]
[ 1313733-33-3 ]
[ 1313732-21-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methanamineHPLC-MS (method 1): Rt=3.157, [M+H]+m/z 478.3.1H NMR (300 MHz, CDCI3) delta 8.49 (s, 1 H), 8.38 (d, J = 8.0, 1 H), 7.51 (t, J = 8.1 , 1 H), 7.29 (t, J = 3.6, 1 H), 5.53 (s, 1 H), 4.51 - 4.41 (m, 2H), 3.55 (d, J = 10.9, 2H), 3.42 (t, J = 5.7, 2H), 3.25 - 3.13 (m, 2H), 2.74 (s, 3H), 2.72 (s, 3H), 2.20 (brs, 1 H), 2.07 - 1.72 (m, 4H). Yield: 48%.

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 94

30
[ 7149-42-0 ]
[ 1313733-34-4 ]
[ 1313732-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong>HPLC-MS (method 1): Rt = 3.32 min, [M+H]+ m/z 492.3.1H NMR (300 MHz, CDCI3) delta 8.61 (s, 1H), 8.46 (d, J = 8.0 Hz, 1 H), 7.52 (m, 1 H), 7.28 (m, 1H), 5.00 (t, J = 5.6 Hz, 1H), 4.43 (m, 2H), 3.36 (t, J = 5.9 Hz, 2H), 3.21 (m, 2H), 2.93 (m, 2H), 2.86 (q, J = 7.2 Hz, 3H), 2.28 (s, 3H), 1.97 (m, 2H), 1.79 (m, 3H), 1.45 (m, 2H), 1.30 (t, J = 7.1 Hz, 3H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 92

31
[ 7149-42-0 ]
C₁₆H₁₃ClF₃N₅O₂ [ No CAS ]
[ 1313732-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methanamineHPLC-MS (method 1): Rt = 3.32 min, [M+H]+ m/z 492.3.1H NMR (300 MHz, CDCI3) delta 8.64 (s, 1 H), 8.47 (d, J = 8.0 Hz, 1 H), 7.51 (m, 1 H), 7.26 (m, 1 H), 4.97 (t, J = 5.7 Hz, 1 H), 4.29 (m, 4H), 3.53 (m, 2H), 3.34 (t, J = 6.0 Hz, 2H), 2.92 (m, 2H), 2.29 (s, 3H), 1.97 (m, 2H), 1.79 (m, 3H), 1.42 (m, 2H), 1.26 (t, J = 7.0 Hz, 3H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 93

32
[ 7149-42-0 ]
[ 1313733-37-7 ]
[ 1313732-45-4 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt = 5.12 min, [M+H]+ m/z 492.3.1H NMR (300 MHz, DMSO) delta 8.58 (s, 1 H), 8.42 (d, J = 8.0 Hz, 1 H), 7.69 (t, J = 8.1 Hz, 1 H), 7.49 (d, J = 8.2 Hz, 1 H), 6.87 (t, J = 5.6 Hz, 1H), 4.29 (d, J = 2.6 Hz, 2H), 3.41 - 3.24 (m, 1H), 3.18 (m, 2H), 2.78 (d, J = 11.0 Hz, 2H), 2.64 (s, 3H), 2.14 (s, 3H), 1.84 (m, 3H), 1.70 (d, J = 12.6 Hz, 2H), 1.36 - 1.14 (m, 2H), 1.07 (d, J = 6.9 Hz, 3H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 106

33
[ 7149-42-0 ]
[ 1313733-39-9 ]
[ 1313732-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt= 3.33 min, [M+H]+ m/z 506.3.1H NMR (300 MHz, DMSO) delta 8.58 (s, 1 H), 8.42 (d, J = 7.7 Hz, 1 H), 7.70 (m, 1 H), 7.50 (m, 1 H), 6.86 (t, J = 5.3 Hz, 1 H), 4.14 (s, 2H), 3.25 (m, 2H), 2.84 (m, 2H), 2.54 (s, 3H), 2.20 (broad s, 3H), 1.90 (m, 1 H), 1.72 (m, 2H), 1.26 (m, 4H), 1.17 (m, 6H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 121

34
[ 7149-42-0 ]
[ 1313733-40-2 ]
[ 1313732-87-4 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt= 3.62 min, [M+H]+ m/z 506.5.H NMR (300 MHz, DMSO) delta 8.58 (s, 1 H), 8.43 (d, J = 8.0 Hz, 1 H), 7.70 (m, 1 H), 7.49 (d, J = 8.6 Hz, 1 H), 6.83 (t, J = 5.4 Hz, 1 H), 4.04 (s, 2H), 3.60 (s, 3H), 3.22 (m, 2H), 3.13 (m, 2H), 2.52 (m, 3H, not clearly seen), 1.93 (m, 1 H), 1.81 (m, 2H), 1.30 (m, 10H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 120

35
[ 7149-42-0 ]
[ 1313733-45-7 ]
[ 1313732-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt= 3.30 min, [M+H]+ m/z 461.2.1H NMR (300 MHz, DMSO) delta 8.57 (s, 1H), 8.44 (m, 1 H), 7.69 (m, 1 H), 7.49 (m, 1 H), 6.92 (t, J = 5.3 Hz, 1 H), 3.23 (t, J = 6.0 Hz, 2H), 2.92 (m, 2H), 2.84 (m, 2H), 2.46 (m, 2H), 2.20 (s, 3H), 1.84 (m, 9H), 1.25 (m, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 105

36
[ 7149-42-0 ]
[ 1313733-59-3 ]
C₁₅H₂₂BrN₇O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 185℃; for 4h;Microwave irradiation;	A mixture of 3-Bromo-5-chloro-6-methyl-7,8-dihydro-6H-9-oxa-1,2,3a,4,6- pentaaza-cyclopenta[a]naphthalene (23 mg, 0.076 mmol) and cyclopropanemethylamine (6 mg, 0.091 mmol) in nBuOH (0.5 mL) was heated under microwave irradiation at 185C for 4 h. The solvent was evaporated under vacuum. The residue was purified by column chromatography (Isolute/Flash, Sill, 0% to 1 % MeOH in DCM) to give (3-bromo-6-methyl-7,8-dihydro-6H-9-oxa- 1 ,2,3a,4,6-pentaaza-cyclopenta[a]naphthalen-5-yl)-(2-methyl-butyl)-amine (10 mg, 39% yield). Following the reaction sequence described for cyclopropylmethyl-[3-(4-fluoro phenyl)-6-methyl-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta[a]naph- thalen-5-yl]-amine starting from 3-bromo-5-chloro-6-methyl-7,8-dihydro-6H-9-oxa 1 ,2,3a,4,6-pentaaza-cyclopenta[a]naphthalene.HPLC-MS (method 1): Rt=3.37 min, [M+H]+m/z 412.2.1H NMR (300 MHz, MeOD) delta 8.26 (dd, J = 9.0, 5.4, 2H), 8.23 (s, 1 H), 7.15 (t, J = 8.8, 2H), 4.43 - 4.32 (m, 2H), 3.43 (d, J = 11.8, 2H), 3.28 (d, J = 6.6, 2H), 3.19 - 3.11 (m, 2H), 2.94 (t, J = 12.5, 2H), 2.75 (s, 3H), 2.67 (s, 3H), 2.19 - 2.02 (m, 1 H), 1.97 (d, J = 13.7, 2H), 1.61 - 1.39 (m, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 139-140

37
[ 7149-42-0 ]
[ 1313733-48-0 ]
[ 1313732-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong>HPLC-MS (method 1): Rt=2.74 min, [ +H]+m/z 419.2.1H NMR (300 MHz, eOD) delta 8.80 (s, 1 H), 8.46 (d, J = 8.1 , 1 H), 8.34 (s, 1 H), 7.73 (d, J = 7.7, 1 H), 7.60 (t, J = 7.9, 1H), 4.43 - 4.35 (m, 2H), 3.44 (d, J = 12.1, 2H), 3.28 (d, J = 6.9, 2H), 3.19 - 3.14 (m, 2H), 3.00 (t, J = 11.5, 2H), 2.76 (s, 3H), 2.68 (s, 3H), 2.24 (s, 1 H), 2.08 (d, J = 10.8, 2H), 1.51 (d, J = 11.7, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 102

38
[ 7149-42-0 ]
[ 1313733-49-1 ]
[ 1313732-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong>HPLC-MS (method 1): Rt=3.20 min, [M+H]+m/z 462.2.H NMR (300 MHz, MeOD) delta 8.88 (s, 1H), 8.59 (d, J = 7.8 Hz, 1 H), 7.71 (dt, J = 15.6, 7.8 Hz, 2H), 4.52 - 4.42 (m, 2H), 3.27 (dd, J = 9.7, 5.6 Hz, 4H), 2.88 (d, J = 11.6 Hz, 2H), 2.76 (s, 3H), 2.24 (s, 3H), 1.98 (t, J = 11.1 Hz, 2H), 1.89 - 1.74 (m, 3H), 1.33 (dt, J = 15.0, 7.5 Hz, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 102

39
[ 7149-42-0 ]
[ 1313733-50-4 ]
[ 1313732-38-5 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1-methyl-4-piperidinyl)methylamineHPLC-MS (method 1): Rt=2.337 min, [M+Hfm/z 433.2.H NMR (300 MHz, MeOD) delta 8.60 (d, J = 1.1 , 1 H), 8.46 (s, 1 H), 7.98 (dd, J = 8.6, 1.5, 1 H), 7.49 (d, J = 8.6, 1 H), 7.35 (d, J = 3.1 , 1 H), 6.65 (t, J = 5.6, 1 H), 6.50 (d, J = 3.2, 1 H), 4.48 - 4.35 (m, 2H), 3.48 (d, J = 1 1.3, 2H), 3.36 (dd, J = 8.4, 4.0, 2H), 3.26 - 3.14 (m, 2H), 2.99 (t, J = 11.5, 2H), 2.79 (s, 3H), 2.70 (s, 3H), 2.22 (d, J = 10.5, 1 H), 2.06 (d, J = 13.5, 2H), 1.59 (dd, J = 23.2, 11.5, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 103

40
[ 7149-42-0 ]
[ 1313733-51-5 ]
[ 1313732-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 180 - 185℃;Microwave irradiation;	A solution of the appropriate chloride (1 eq) (ex: 5-chloro-6-methyl-3-(3- trifluoromethoxy-phenyl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-cyclopenta- (ajnaphthalene) and the appropriate amine (3 to 5 eq) (ex: 1-methyl-piperidin-4- ylamine) in nBuOH (15 mL/mmol) was heated up to 180- 185C under microwave irradiation for 5 h - 10 h (or 24 h at 160-180C in a silicon bath). The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) or by semi-preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1 % formic acid; Solvent B: acetonitrile with 0.1 % formic acid. Gradient: 40% of A to 0% of A).The NH-BOC-protected amines got deprotected in the reaction conditions and reacted giving a mixture of regioisomers. Amine: (1 -methyl-4-piperidinyl)methylamineHPLC-MS (method 1 ): Rt = 0.32, 2.29 min, [M+H]+ m/z 437.4.1H NMR (300 MHz, CDCI3) delta 7.94 (m, 1 H), 7.89 (d, J = 7.8 Hz, 1 H), 7.34 (m, 1 H),6.83 (m, 1 H), 5.07 (t, J = 5.6 Hz, 1 H), 4.47 (m, 2H), 3.38 (t, J = 6.0 Hz, 2H), 3.20(m, 2H), 3.09 (d, J = 11.6 Hz, 2H), 3.03 (s, 6H), 2.74 (s, 3H), 2.40 (s, 3H), 2.16(m, 2H), 1.84 (m, 3H), 1.57 (m, 2H).

Reference： [1]Patent: WO2011/80510,2011,A1 .Location in patent: Page/Page column 86-87; 103

41
[ 7149-42-0 ]
[ 1331742-76-7 ]
[ 1331741-85-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With pyridine; at -10℃; for 2h;	Preparation of final product 2-14 A solution of the intermediate I-05, 3-(4-Methoxy-phenyl)-5-trifluoromethanesulfonyloxy-3H-[1,2,3]triazolo[4,5-b]pyridine-6-carboxylic acid ethyl ester (0.10 g; 0.224 mmol), in dry pyridine (2 mL) was cooled to -10 C and <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (0.086 g; 0.672 mmol) was added. The resulting solution was stirred for 2h at this temperature, then allowed to reach room temperature over the weekend. Evaporation of the solvent followed by aqueous workup (DCM/Bicarb drying Na2S0 ) gave a brown oil that was purified on silica (Biotage 12M; DCM with 5% MeOH 4 CV, gradient to 25% MeOH over12 CV). The final product 2-14, 3-(4-Methoxy-phenyl)-5-[(1-methyl-piperidin-4-ylmethyl)-amino]-3H-[1,2,3]triazolo[4,5-b]pyridine-6-carboxylic acid ethyl was isolated as an orange solid; in total, 52 mgs were obtained (Y: 55%).

Reference： [1]Patent: WO2011/101644,2011,A1 .Location in patent: Page/Page column 86; 87

42
[ 7149-42-0 ]
[ 1331742-80-3 ]
[ 1331741-90-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine; In ethanol; at 90℃; for 72h;	Preparation of final product 2-19 5-Chloro-3-(3-trifluoromethoxy-phenyl)-3H-[1 ,2,3]triazolo[4,5-b]pyridine (0.050 g; 0. 59 mmol), intermediate I-08, and (1-Methyl-4-piperidinyl)methanamine (0.041 g; 0.318 mmol) were dissolved in dry ethanol (2 mL). Triethylamine (22 uL; 0.159 mmol) was added and the reaction was heated at 90 C sandbath temp for 72 h. The solvent was evaporated and the crude product was treated with DCM/NaOH (0.1 M). Drying and evaporation gave a yellow solid that was further purified (Biotage 12S. DCM + 10% MeOH 5 CV, ramp to 25% MeOH over 10 CV. MeOH with 1 % TEA: Thus, the final product 2-19, (1 -Methyl-piperidin-4-ylmethyl)-[3- (3-trifluoromethoxy-phenyl)-3H-[1 ,2,3]triazolo[4,5-b]pyridin-5-yl]-amine, was isolated obtaining 36.9 mgs of a pale-yellow solid (Y: 57%).

Reference： [1]Patent: WO2011/101644,2011,A1 .Location in patent: Page/Page column 87; 88
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1591 - 1597

43
[ 7149-42-0 ]
[ 1375082-04-4 ]
[ 1375082-28-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3349 - 3353

44
[ 7149-42-0 ]
[ 1375082-11-3 ]
[ 1375082-40-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3349 - 3353

45
[ 7149-42-0 ]
[ 1390624-34-6 ]
[ 1390623-39-8 ]

Yield	Reaction Conditions	Operation in experiment
51%	In butan-1-ol; at 170℃;Microwave irradiation;	A solution of the appropriate chloride (e.g. 5-chloro-6-methyl-3-(2-trifluoromethyl- pyridin-4-yl)-7,8-dihydro-6H-9-oxa-1 ,2,3a,4,6-pentaaza-benz[e]indene) and the appropriate amine (5 eq) (e.g. <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong>) in nBuOH was heated at 170C under microwave irradiation for 6 h to 48 h. When the amine was a hydrochloride salt, DIPEA (5 eq.) was added. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (Isolute/Flash, Sill, 2.5% MeOH with 7N ammonia in DCM) followed by semi- preparative HPLC (Gemini C18 (150 10 mm; 5 m), Solvent A: water with 0.1% formic acid; Solvent B: acetonitrile with 0.1% formic acid. Gradient: 40% of A to 0% of A). Some compounds were isolated as their corresponding formic acid salts.When the diamine was monoBoc-protected, deprotection of the Boc-protected compounds was achieved by treatment either with MeOH (10 mLJmmol) and HCI (4M in dioxane) (6 eq) at RT overnight (after evaporation, the final compounds were obtained as their corresponding hydrochloric salts) or with MeOH (10 mL/mmol) and Amberlyst (10 eq) at RT overnight and, after treatment with 7N NH3 in MeOH, the final compounds were obtained in the free base form.

Reference： [1]Patent: WO2012/98387,2012,A1 .Location in patent: Page/Page column 93; 95

46
[ 7149-42-0 ]
3-fluoro-4-nitrobenzophenone [ No CAS ]
C₂₀H₂₃N₃O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5264 - 5267

47
[ 7149-42-0 ]
[ 1208988-03-7 ]
C₂₇H₃₇N₇O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5652 - 5657

48
[ 7149-42-0 ]
[ 1369487-49-9 ]
[ 1401618-75-4 ]

Yield	Reaction Conditions	Operation in experiment
		1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-hydroxybenzotriazole (68.1 mg, 0.504 mmol) and EDCI (97 mg, 0.504 mmol) were dissolved in DCM (Volume: 4.0 ml). The suspension was stirred at room temperature for 10 minutes where it turned clear. Hunig'sBase (0.132 ml, 0.756 mmol) and (1-methylpiperidin-4-yl)methanamine (100 mg, 0.780 mmol) were added. The reaction was stirred at room temperature overnight. It was diluted with water and ethyl acetate. The water layer was washed with another portion of ethyl acetate. The combined organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The resulting crude material was triturated with diethyl ether/ethyl acetate to afford the product as a white solid. (Yield: 83 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.77, 7.62, 7.54, 7.35-7.30, 7.21, 7.13-7.06, 6.72, 5.49, 4.38, 4.02, 2.93, 2.78, 2.42-2.30, 2.17, 1.77, 1.57, 1.45-1.02

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9222 - 9241
[2]Patent: US2012/252807,2012,A1 .Location in patent: Page/Page column 54

49
[ 7149-42-0 ]
[ 1403819-76-0 ]
[ 1403817-54-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example No. 151Preparation of (7- (( (l-methylpiperidin-4-yl) methyl) amino) -1H- pyrazolo [4, 3-d] pyrimidin-5-yl) (phenyl) methanone (7-chloro-2- (4 -methoxybenzyl) -2H-pyrazolo [4 , 3-d] pyrimidin-5- yl) (phenyl) methanone (0.16 mmol) and (l-methylpiperidin-4- yl) methanamine (0.3 mmol 2 eq. , ) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 350.2200 g/molHPLC-MS: analytical method Lrt: 2.92 min - found mass: 351 (m/z+H)

Reference： [1]Patent: WO2012/143144,2012,A1 .Location in patent: Page/Page column 261; 262

50
[ 7149-42-0 ]
[ 1417699-10-5 ]
[ 1417698-87-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 1,4-dioxane; for 5h;Reflux;	General procedure: General Synthetic Procedure BTo a suspension of Intermediate 1-21 (30 mg, 0.08 mmol), (1-methyl-4- piperidinyl)methanamine (21 mg, 0.16 mmol), Na'BuO (23 mg, 0.24 mmol) and rac-BINAP (10 mg, 0.02 mmol) in dioxane (1.5 mL) was added Pd2(dba)3 (7 mg, 0.008 mmol). The reaction mixture was refluxed for 5 h. On cooling, sat. aq. sol. NaHC03 was added and the mixture was extracted with CHCI/PrOH (1:1). The organic layers were dried, filtered and evaporated. The residue was purified by column chromatography (DCM/ eOH 100:0 to 90:10 and DC /1M NH3 in MeOH 4:1) to give Final Product 10 (15 mg, 40%).

Reference： [1]Patent: WO2013/5041,2013,A1 .Location in patent: Page/Page column 76

51
[ 7149-42-0 ]
[ 64-18-6 ]
[ 1417848-92-0 ]
[ 1417840-38-0 ]

Yield	Reaction Conditions	Operation in experiment
2%		General procedure: Example: Synthesis of final product 24To a suspension of Intermediate 1-52 (77 mg, 0.21 mmol), (1-methyl-4- piperidinyl)methanamine (53 mg, 0.41 mmol), Na'BuO (60 mg, 0.62 mmol) and rac-BINAP (26 mg, 0.042 mmol) in dioxane (5 mL) was added Pd2(dba)3 (19 mg, 0.021 mmol). The mixture was degassed and refluxed for 3 h. On cooling, sat aq NaHC03 was added, and the mixture was extracted with CHCI PrOH 1 :1. The organic layers were dried, filtered and concentrated. The residue was purified by column chromatography (DCM/ eOH 100:0 to 90:10 then DCM/1 M NH3 in MeOH 90:10) and by prep-HPLC to give Final Product 24 (2 mg, 2%) as formic salt.

Reference： [1]Patent: WO2013/4984,2013,A1 .Location in patent: Page/Page column 92

52
[ 7149-42-0 ]
[ 1417848-07-7 ]
[ 1417837-93-4 ]

Yield	Reaction Conditions	Operation in experiment
32 mg	In N,N-dimethyl acetamide; at 100℃; for 8h;	General procedure: Exam le: Synthesis of final product 1A mixture of <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (101 mg, 0.78 mmol) and Intermediate 1-42 (100 mg, 0.26 mmol) in DMA (5 mL) was heated at 100 C for 8 h. The solvents were removed in vacuo and the residue was purified by column chromatography (DCM/7N NH3 in MeOH 100:0 to 98:2). The product obtained was triturated from Et20 to afford Final Product 1 (32 mg) as a white solid.

Reference： [1]Patent: WO2013/4984,2013,A1 .Location in patent: Page/Page column 90-91

53
[ 7149-42-0 ]
[ 32315-10-9 ]
1-[1-(4-chlorophenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl]piperazine dihydrochloride [ No CAS ]
[ 1427588-65-5 ]

Yield	Reaction Conditions	Operation in experiment
38%		Triphosgene (14.2 mg, 0.05 mmol) was dissolved in DCM (1 mL) and a solution of <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (18.4 mg, 0.14 mmol) and DIPEA (25.0 pL, 0.14 mmol) in DCM (1 mL) was added. The reaction mixture was stirred for 1 h and a solution of Intermediate 50 (37.0 mg, 0.10 mmol) and DIPEA (25.0 pL, 0.14 mmol) in DCM (1 mL) was added. The reaction mixture was stirred for 18 h, diluted with DCM (10 mL), washed with sat aq NH4Cl (5 x 10 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase chromatography to give the title compound as a yellow solid (17.0 mg, 38%). LCMS (ES+): 468.0 [MH]+. HPLC: Rt 4.13 min, 98.7% purity.
38%		Example 51 4-[1-(4-Chlorophenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl]-N-[(1-methylpiperidin-4-yl)methyl]piperazine-1-carboxamide Triphosgene (14.2 mg, 0.05 mmol) was dissolved in DCM (1 mL) and a solution of <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (18.4 mg, 0.14 mmol) and DIPEA (25.0 muL, 0.14 mmol) in DCM (1 mL) was added. The reaction mixture was stirred for 1 h and a solution of Intermediate 50 (37.0 mg, 0.10 mmol) and DIPEA (25.0 muL, 0.14 mmol) in DCM (1 mL) was added. The reaction mixture was stirred for 18 h, diluted with DCM (10 mL), washed with sat aq NH4Cl (5*10 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase chromatography to give the title compound as a yellow solid (17.0 mg, 38%). LCMS (ES+): 468.0 [MH]+. HPLC: Rt 4.13 min, 98.7% purity.

Reference： [1]Patent: WO2013/38189,2013,A1 .Location in patent: Page/Page column 78
[2]Patent: US2014/275063,2014,A1 .Location in patent: Paragraph 0266; 0267

54
[ 7149-42-0 ]
[ 1427555-87-0 ]
[ 1427588-56-4 ]

Yield	Reaction Conditions	Operation in experiment
11%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 19h;	Intermediate 47 (66.0 mg, 0.17 mmol) was dissolved in DMF (2 mL), cooled to 0 00 and HBTU (63.3 mg, 0.17 mmol), <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (25.7 mg, 0.20 mmol) and DIPEA (58.2 pL, 0.33 mmol) were added. The reaction mixture was stirred at 0 C for 1 h and at RT for 18 h, diluted with DCM (10 mL) and washed with sat aq NH4Cl (3 x 5 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a yellow solid (8.62 mg, 11%). LCMS (ES+): 467.0 [MH]+. HPLC: Rt 4.19 min, 100% purity.
11%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 19h;	Example 43 1-[1-(4-Chlorophenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl]-N-[(1-methylpiperidin-4-yl)methyl]piperidine-2-carboxamide Intermediate 47 (66.0 mg, 0.17 mmol) was dissolved in DMF (2 mL), cooled to 0 C. and HBTU (63.3 mg, 0.17 mmol), <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (25.7 mg, 0.20 mmol) and DIPEA (58.2 muL, 0.33 mmol) were added. The reaction mixture was stirred at 0 C. for 1 h and at RT for 18 h, diluted with DCM (10 mL) and washed with sat aq NH4Cl (3*5 mL). The organic fraction was dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a yellow solid (8.62 mg, 11%). LCMS (ES+): 467.0 [MH]+. HPLC: Rt 4.19 min, 100% purity.

Reference： [1]Patent: WO2013/38189,2013,A1 .Location in patent: Page/Page column 74
[2]Patent: US2014/275063,2014,A1 .Location in patent: Paragraph 0253; 0254

55
[ 7149-42-0 ]
[ 1253585-66-8 ]
[ 1253584-89-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a stirred solution of 47 (107 mg, 0.3 mmol) in dimethylacetamide(3 mL) was added N,N,N0 ,N0-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (TBTU) (115 mg, 0.36 mmol) Afterstirring for 15 min at room temperature, N,N-diisopropylethylamine(0.104 mL, 0.6 mmol) and 2-fluoroethylamine hydrochloride(45 mg, 0.45 mmol) were added. After stirring overnight, thereaction mixture was poured into a saturated solution of sodiumhydrogen carbonate and thoroughly extracted with EtOAc, washedwith brine, dried over Na2SO4 and evaporated to dryness. The residuewas purified by Biotage SP1 flash chromatography (gradientelution from 2% to 10% of MeOH in DCM) to afford 8 (86 mg,71%).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 7047 - 7063

56
[ 7149-42-0 ]
polystyrene carboxaldehyde resin [ No CAS ]
C₈H₁₇N₂Pol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2908 - 2919

57
[ 7149-42-0 ]
[ 39859-36-4 ]
4-bromo-2-[[(1-methyl-4-piperidyl)methylamino]phenylmethyl]aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		A mixture of (2-Amino-5-bromo-phenyl)-phenyl-methanone (1 g, 3.6 mmol), 1-Methyl-4-methylaminopiperidine (0.46 g, 3.6 mmol) and Ti(OEt)4 (1.65 g, 7.2 mmol) in THF (30 ml) is stirred at 66 C. over night. The mixture is cooled to rt, poured onto an ice-water-mixture and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. EtOH (10 ml) and sodium borohydride (0.57 g, 15.1 mmol) is added and the mixture stirred at rt for 72 h. Water is added and the mixture is extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is used without further purification. Yield: 1.05 g (75%) HPLC-MS: M+H=388/390; tRet=1.79 min; AM11
		4-Bromo-2- [ [(l-methyl-4-piperidyl)methylamino] -phenyl-methyl] aniline A mixture of (2-Amino-5-bromo-phenyl)-phenyl-methanone (1 g, 3.6 mmol), l-Methyl-4-methylaminopiperidine (0.46 g, 3.6 mmol) and Ti(OEt)4 (1.65 g, 7.2 mmol) in THF (30 ml) is stirred at 66C over night. The mixture is cooled to rt, poured onto an ice-water-mixutre and extracted with EtOAc. The combined organic layers are dried over MgS04 and concentrated in vacuo. EtOH (10 ml) and sodium boro hydride (0.57 g, 15.1 mmol) is added and the mixture stirred at rt for 72 h. Water is added and the mixture is extracted with EtOAc. The combined organic layers are dried over MgS04 and concentrated in vacuo. The product is used without further purification. Yield: 1.05 g (75%) HPLC-MS: M+H=388/390; tRet =1.79 min; AMI 1

Reference： [1]Patent: US2014/296230,2014,A1 .Location in patent: Paragraph 0193-0196
[2]Patent: WO2014/154762,2014,A1 .Location in patent: Page/Page column 43

58
[ 7149-42-0 ]
[ 1780-31-0 ]
C₁₂H₁₉ClN₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 8099 - 8110

59
[ 7149-42-0 ]
[ 1780-31-0 ]
[ 1616597-89-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 8099 - 8110

60
[ 7149-42-0 ]
[ 1361951-79-2 ]
[ 1361951-49-6 ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 63 - 67

61
[ 7149-42-0 ]
3-(4-nitro-1H-pyrazol-1-yl)benzoic acid [ No CAS ]
C₁₇H₂₁N₅O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10013 - 10030

62
[ 7149-42-0 ]
[ 253870-02-9 ]
C₁₅H₂₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h;Inert atmosphere;	General procedure: A solution of compound 2 (167 mg, 1 mmol), EDC·HCl (230mg, 1.2mmol) and HOBt (162mg, 1.2mmol) in DMF (15mL) was stirred at 0-4C under the atmosphere of nitrogen for 20min. The substituted amine a-f (2 mmol) was added to the mixture and stirred at the same temperature for 30 min and then overnight at room temperature. The mixture was diluted with water and adjusted to pH 9 with saturated Na2CO3 solution and then extracted with dichloromethane and methanol (9:1, v/v). The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure to provide crude product 3a-f (50-60%) as red oils.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2782 - 2787

63
[ 7149-42-0 ]
[ 1312661-98-5 ]
[ 1312662-85-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: General Displacement Procedure: 2 dram round bottomed vials were charged with(Z)-5-((2-(methylsulfonyl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (25 mg, 0.0877 mmol) prepared according to thegeneral procedure, DMSO (1 mL, 0.08 M), diisopropylethylamine (50 muL, 0.288mmol, 3.2 equiv.), and the appropriate amine (0.0877 mmol, 1.0 equiv.). The reaction mixture was heated to 110C and shaken for 24 h. The solvent was removed under reduced pressure (genvacHT-4) and the crude residues were purified using reverse phase HPLC (MS-triggered fraction collection) with an acetonitrile/water gradient andtriflouroacetic acid as a modifier. Thepure fractions were then concentrated under reduced pressure (GenevacHT-4). (Z)-5-((2-(((1-methylpiperidin-4-yl)methyl)amino)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione(10) was prepared using the general displacement procedure and the generalde-protection procedure with 1-(methylpiperidin-4-yl)methanamine (7.4 mg, 29.2mg theoretical, 25.3%). LC-MS m/z 334.1(M+1).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 3186 - 3190

64
[ 7149-42-0 ]
5-fluoro-N²-[3-methoxy-5-(5-methyl-1H-tetrazol-1-yl)phenyl]-N⁴-[(1-methylpiperidin-4-yl)methyl]pyrimidine-2,4-diamine dihydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3269 - 3277

65
[ 7149-42-0 ]
[ 2927-71-1 ]
2-chloro-5-fluoro-N-[(1-methylpiperidin-4-yl)methyl]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; for 16h;	To a solution of 3 (500 mg, 3.0 mmol) in MeOH (5 mL), <strong>[7149-42-0](1-methyl-4-piperidinyl)methanamine</strong> (380 mg, 3.0 mmol) was added. The reaction mixture was stirred at room temperature for 16 h and then diluted with CHCl3 and basified with saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel with elution using (CHCl3-MeOH) (97:3) to give 4b (295 mg, 38%) as a colorless solid. 1H NMR (DMSO-d6) delta 1.09-1.23 (2H, m), 1.48-1.66 (3H, m), 1.72-1.83 (2H, m), 2.12 (3H, s), 2.67-2.77 (2H, m), 3.17-3.25 (2H, m), 8.04 (1H, d, J = 3.6 Hz), 8.18 (1H, br s); MS (ESI) m/z 259, 261 [M+H]+.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3269 - 3277
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 7195 - 7216

66
[ 7149-42-0 ]
[ 1201-07-6 ]
8-bromo-2-methyl-N-[(1-methyl-4-piperidinyl)methyl]-4-quinolinamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 7021 - 7056

67
[ 7149-42-0 ]
[ 1201-07-6 ]
2-methyl-4-[(1-methyl-4-piperidinyl)methyl]amino}-8-quinolinecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 7021 - 7056

68
[ 7149-42-0 ]
[ 90417-53-1 ]
5-methoxy-N-[(1-methylpiperidin-4-yl)methyl]-1H-indazole-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8920 - 8937

69
[ 7149-42-0 ]
C₂₅H₂₆ClFN₆O₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 7195 - 7216

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
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.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
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:
P371	In case of major fire and large quantities:
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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. 7149-42-0 ]

Quality Control of [ 7149-42-0 ]

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Calculated chemistry of [ 7149-42-0 ]

Physicochemical Properties

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Lipophilicity

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Medicinal Chemistry

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Application In Synthesis of [ 7149-42-0 ]

[ 7149-42-0 ] Synthesis Path-Upstream 1~3

[ 7149-42-0 ] Synthesis Path-Downstream 1~69

Related Functional Groups of [ 7149-42-0 ]

Amines

Related Parent Nucleus of [ 7149-42-0 ]

Piperidines

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

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[ 7149-42-0 ]

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[ 7149-42-0 ]