[ CAS No. 612511-81-6 ] {[proInfo.proName]}

Name: 612511-81-6|(1-Methyl-1H-pyrazol-3-yl)methanamine|97%
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SKU: A906897
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Quality Control of [ 612511-81-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 612511-81-6 ]

CAS No. :	612511-81-6	MDL No. :	MFCD03419807
Formula :	C₅H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SSXDUSOCSNXBPO-UHFFFAOYSA-N
M.W :	111.15	Pubchem ID :	7019419
Synonyms :

Calculated chemistry of [ 612511-81-6 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.16
TPSA :	43.84 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) :	-7.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.18
Log Po/w (XLOGP3) :	-0.87
Log Po/w (WLOGP) :	-0.27
Log Po/w (MLOGP) :	-0.53
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	-0.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.38
Solubility :	46.6 mg/ml ; 0.419 mol/l
Class :	Very soluble
Log S (Ali) :	0.43
Solubility :	300.0 mg/ml ; 2.7 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.78
Solubility :	18.4 mg/ml ; 0.166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 612511-81-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 612511-81-6 ]

* 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 [ 612511-81-6 ]
Downstream synthetic route of [ 612511-81-6 ]

[ 612511-81-6 ] Synthesis Path-Upstream 1~1

1
[ 89179-62-4 ]
[ 612511-81-6 ]
[ 37599-58-9 ]

Reference： [1] Patent: WO2003/82861, 2003, A2, . Location in patent: Page/Page column 50-51

[ 612511-81-6 ] Synthesis Path-Downstream 1~88

1
[ 612511-81-6 ]
[ 1058129-39-7 ]
[ 1058129-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 120℃; for 3h;	To a solution of 9-bromo-l,6-dichloro-benzo[c][l,6]naphthyridine (0.10 g, 0.31 mMol) in anhydrous CH3CN (4.0 mL) was added C-(I -methyl- lH-pyrazol-3-yl)-methylamine (0.040 g 0.36 mMol) and anhydrous Et3N (0.22 mL, 1.6 mMol). The reaction mixture was heated in a sealed tube at 12O0C. After 3 hours the solvent was removed and the solid obtained was re-dissolved in EtOAc (10 mL). The EtOAc layer was washed with water (2 x 5 mL), brine (1 x 10 mL), and dried over MgSO4. The filtrate was concentrated and the resulting residue was purified using preparative HPLC to afford 9-bromo- 1 -chloro-N- [( 1 -methyl- 1 //-pyrazol-3 - yl)methyl]benzo[c]-l,6-naphthyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) deltal 1.34 (br d, IH), 10.11 (d, IH), 8.61 (t, IH), 8.32 (d, IH), 7.75-7.73 (dd, IH), 7.55 (d, IH), 7.37 (t, IH), 6.40 (d, IH), 6.18 (d, IH), 4.74 (d, 2H), 3.77 (s, 3H). LRMS calculated for C17H14BrClN5 [M+H]+, 404.0; found 403.9.

Reference： [1]Patent: WO2008/112217,2008,A1 .Location in patent: Page/Page column 105

2
[ 612511-81-6 ]
[ 1219623-42-3 ]
[ 1219623-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Example 4; 7V-[(l-methyl-lH-pyrazol-3-yl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-l-yl)acetamide; N1-((ethylimino)methylene)-Lambda/3,Lambda/3-dimethylpropane-l,3-diamine hydrochloride (0.049 g, 0.254 mmol) , 2-(2-oxo-3,3-diphenylpyrrolidin-l-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and (1 -methyl- lH-pyrazol-3-yl)methanamine (0.021 g, 0.186 mmol) were combined and stirred together in dichloromethane (0.5 mL) at room temperature. After stirring overnight, the reaction was loaded directly onto a SF 10-8 silica gel column (Analogix.(R)., Burlington, WI), and the title compound was eluted using a gradient of 0.4percent to 7.5percent methanol/dichloromethane over 20 minutes (flow = 20 mL/minute). 1H NMR (300MHz, CDCl3) delta ppm 7.23-7.34 (m, 11 H), 6.40 (t, J= 6.0 Hz, 1 H), 6.06 (d, J= 2.2 Hz, 1 H), 4.38 (d, J= 5.3 Hz, 2 H), 4.05 (s, 2 H), 3.82 (s, 3 H), 3.50 (t, J= 6.4 Hz, 2 H), 2.82 (t, J= 6.4 Hz, 2H); MS (ESI-) m/z 387 (M-H)".

Reference： [1]Patent: WO2010/39947,2010,A1 .Location in patent: Page/Page column 62

3
[ 612511-81-6 ]
[ 1350522-88-1 ]
C₁₉H₁₉Cl₂N₅O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7715 - 7730

4
[ 612511-81-6 ]
[ 848694-76-8 ]
[ 1196886-83-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 130℃; for 12h;	To a solution of ethyl 2-(2-amino-4-chloro-6-((l-methyl-lH-pyrazol-3- yl)methylamino)pyrimidin-5-yl)acetate (2.8 g, 8.64 mmol) in n-BuOH (20 mL) was added DIEA (2.5 g, 19.38 mmol). The resulting solution was stirred at 1300C for 12 hr and the solids were collected by filtration, resulted in 2.0 g (83percent) of 2-amino-4-chloro-7-((l -methyl - lH-pyrazol-3-yl)methyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one as a white solid.

Reference： [1]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 139

5
[ 612511-81-6 ]
[ 1330595-45-3 ]
[ 1400872-78-7 ]

Yield	Reaction Conditions	Operation in experiment
11%		Example 1trans-N-[Z-{2-[(i -Methyl-1 H-pyrazol-3-yl)methyl]amino}pyrimidin-5-yl)imidazo[1 ,2- .pound.>]pyridazin-6-yl]cyclohexane-1,4-diamineA solution of intermediate 2 (60 mg, 0.12 mmol, 1.0 eq) in dioxane (2 mL) was treated with 1-(1 -methyl-1 H-pyrazol-3-yl)methanamine (54 mg, 0.49 mmol, 4.0 eq) and stirred at reflux for 4 h. Concentration in vacuo, purification by preparative HPLC and treatment with 4M HCI in dioxane (1 mL) followed by elution through an aminopropyl cartridge gave an off- white solid (6 mg, 11 percent); 1H NMR (400 MHz, DMSO-dB) delta ppm 9.00 (br. s, 2H), 7.81-7.65 (m, 3H), 7.55 (d, J=2.3 Hz, 1 H), 6.93 (d, J=6.9 Hz, 1 H), 6.62 (d, J=9.6 Hz, 1 H), 6.13 (d, J=2.3 Hz, 1 H), 4.47 (d, J=6.0 Hz, 2H), 3.77 (s, 3H), 3.55-3.40 (m, 1 H), 2.64-2.54 (m, 1 H), 2.15-2.03 (m, 2H), 1.89-1.74 (m, 2H), 1.37-1.08 (m, 4H); m/z (ES+APCI)+: 419 [ +H]+.

Reference： [1]Patent: WO2012/127212,2012,A1 .Location in patent: Page/Page column 58-59

6
[ 612511-81-6 ]
[ 1369487-49-9 ]
[ 1401618-77-6 ]

Yield	Reaction Conditions	Operation in experiment
		N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (259 mg, 1.350 mmol), 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (428 mg, 1.080 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (182 mg, 1.350 mmol) were dissolved in 4.0 mL of DCM.The reaction was stirred at room temperuatre for ten minutes before Hunig'sBase (0.236 ml, 1.350 mmol) and <strong>[612511-81-6](1-methyl-1H-pyrazol-3-yl)methanamine</strong> (100 mg, 0.900 mmol) as a 1.0 mL DCM solution was added.The reaction was allowed to stir at room temperature overnight.The reaction was diluted with water and ethyl acetate.The organic layer was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride.The organic phase was dried over magnesium sulfate, filtered and concentrated.The resulting material was triturated with ethyl acetate to obtain white solid as the product. 1H-NMR (400 MHz, DMSO-d6) 8.18, 7.66-7.51, 7.35, 7.22, 7.12, 6.73, 6.05, 5.49, 4.40, 4.18, 3.96, 3.77, 2.93, 2.41, 1.69, 1.44

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

7
[ 612511-81-6 ]
(S)-3-benzyl 5-ethyl 6-(chloromethyl)-4-(2,4-dichlorophenyl)-2-methylpyridine-3,5-dicarboxylate [ No CAS ]
C₂₇H₂₂Cl₂N₄O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7343 - 7357

8
[ 612511-81-6 ]
[ 1330595-45-3 ]
C₂₆H₃₄N₁₀O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3570 - 3587

9
[ 17827-61-1 ]
[ 612511-81-6 ]

Reference： [1]Patent: WO2014/139150,2014,A1
[2]Patent: WO2014/150114,2014,A1

10
[ 612511-81-6 ]
4-bromo-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one [ No CAS ]
6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methyl-4-((1-methyl-1H-pyrazol-3-yl)methylamino)pyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 85℃; for 4h;Inert atmosphere;	To the solution of 4-bromo-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl) methoxy)-2-methylpyridazin-3(2H)-one (73 mg, 0.2 mmol) in toluene (4 mL) underNz, (1-methyl-1Hpyrazol-3-yl)methanamine (22 mg, 0.2 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), BINAP (18 mg,20 0.03 mmol) and Na01Bu (29 mg, 0.3 mmol) were added. After the reaction mixture was stirred at85 °C for 4 h, 15 mL water was added. The mixture was extracted with EtOAc (3 x 10 mL). Thecombined organics were dried over MgS04, filtered and concentrated in vacuo. The residue waspurified by Pre-HPLC to afford the title compound as a solid. 1H NMR (400 MHz, MeOD) o8.06 (d, 1H), 7.50(d, 1H), 7.30 (dd, 1H), 7.17 (d, 1H), 6.21 (d, 1H), 5.83 (s, 1H), 4.32 (s, 2H),25 4.18-4.14 (m, 1H), 4.06-4.02 (m, 1H), 3.87 (s, 3H), 3.84 (s, 3H), 3.62 (s, 3H), 2.09 -2.04 (m,1H), 1.76- 1.72(m, 1H), 1.20-1.15 (m, 1H), 1.05-1.00 (m, 1H); LRMS m/z (M+H) 397.2 found,3 97.19 required.
	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 85℃; for 4h;Inert atmosphere;	Step D: 6-(((l S.2S)-2-(5-methoxypyridin-2-yl)cvclopropyl)methoxy)-2-methyl-4-((l-methyl- lH-pyrazol-3-yl)methylamino)pyridazin-3(2H)-one (6)To the solution of 4-bromo-6-(((lS,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl) methoxy)-2- methylpyridazin-3(2H)-one (73 mg, 0.2 mmol) in toluene (4 mL) under N2, ( 1 -methyl- 1H- pyrazol-3-yl)methanamine (22 mg, 0.2 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), BetaGammaNuAlphaRho (18 mg, 0.03 mmol) and NaOlBu (29 mg, 0.3 mmol) were added. After the reaction mixture was stirred at 85 °C for 4 h, 15 mL water was added. The mixture was extracted with EtOAc (3 x 10 mL). The combined organics were dried over MgS04, filtered and concentrated in vacuo. The residue was purified by Pre-HPLC to afford the title compound as a solid. 1H NMR (400 MHz, MeOD) delta 8.06 (d, 1H), 7.50(d, 1H), 7.30 (dd, 1H), 7.17 (d, 1H), 6.21 (d, 1H), 5.83 (s, 1H), 4.32 (s, 2H), 4.18- 4.14 (m, 1H), 4.06-4.02 (m, 1H), 3.87 (s, 3H), 3.84 (s, 3H), 3.62 (s, 3H), 2.09 -2.04 (m, 1H), 1.76- 1.72(m, 1H), 1.20-1.15 (m, 1H), 1.05-1.00 (m, 1H); LRMS m/z (M+H) 397.2 found, 397.19 required.

Reference： [1]Patent: WO2014/139150,2014,A1 .Location in patent: Page/Page column 65; 66
[2]Patent: WO2014/150114,2014,A1 .Location in patent: Page/Page column 666

11
[ 612511-81-6 ]
C₁₉H₂₄N₄O₅ [ No CAS ]
(S)-3-(1'-methyl-1H-pyrazol-3'-methyl)5-((carboxybenzylamino)butyl)-2,4-imidazolidinedione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
140 mg	With potassium carbonate; for 2h;Milling;	General procedure: (Step 1) The -amino methyl ester hydrochloride (1.0equiv.) and 1,1?-carbonylimidazole (CDI) (1.3 equiv.) were ground in a 12 mLstainless steel milling jar in a planetary ball-mill at 450 rpm for 40 minutes. (Step 2)The amine (1.6 equiv) and K2CO3 (3.6 equiv) were added and the mixture wasground at 450 rpm for two hours. Distilled water was added to the crude and thedesired compound was either precipitated and filtered over sintered glass, orextracted with ethyl acetate. The organic layer was washed with a 10percent aq. citric acidsolution (× 3) and brine (× 1), dried over MgSO4 and concentrated in vacuo. Only forcompounds 3b and 5b a purification by flash chromatography was performed on thecrude sample, respectively.

Reference： [1]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 19 - 25

12
[ 612511-81-6 ]
5-((3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-1-(tert-butoxycarbonyl)piperidin-4-yl)-2-fluorobenzoic acid [ No CAS ]
tert-butyl (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluoro-3-(((1-methyl-1H-pyrazol-3-yl)methyl)carbamoyl)phenyl)-piperidine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3052 - 3069

13
[ 612511-81-6 ]
C₁₆H₂₀N₂O₄ [ No CAS ]
C₂₁H₂₉N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In isopropyl alcohol; at 50℃; for 16h;	To a solution of Oxirane intermediate (16.0 g, 52.56 mmol) in iPrOH (200 ml), was added (1-methyl-1 H-pyrazol-3-yl)methanamine (8.76 g, 78.84 mmol). The reaction mixture was stirred under 50°C for 16 h, after that RM was concentrated under reduced pressure and purified by silica column chromatography using 100percent ethyl acetate as eluent to give (8.8 g, 40 percent) as a thick liquid.

Reference： [1]Patent: WO2017/197324,2017,A1 .Location in patent: Page/Page column 90

14
[ 612511-81-6 ]
3-[1-(azetidin-3-ylsulfonyl)piperidin-4-yl]-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
N-[(1-methylpyrazol-3-yl)methyl]-3-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]sulfonylazetidine-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.39 mg		To a solution of <strong>[612511-81-6](1-methylpyrazol-3-yl)methanamine</strong> (9.58 tL, 1 equiv.) in dry DCM (1 mL), CDI (17.83 mg, 1.1 equiv.) was added. The reaction mixture was stirred at room temperature for 2 hours. Then, 3-[1 -(azetidin-3 -ylsulfonyl)-4-piperidyl] - 1H-pyrrolo [2,3 - b]pyridine (32 mg, 1 equiv.) was added and stirring was continued at room temperature overnight. Solvent was removed in vacuo and the obtained residue was purified bypreparative LC-MS to afford the expected product (6.39 mg). LCMS: MW (calcd): 457.55; MS (ES, m/z): 458.13 [M+H].

Reference： [1]Patent: WO2018/78360,2018,A1 .Location in patent: Page/Page column 162; 233

15
[ 612511-81-6 ]
C₃₈H₅₃FN₂O₁₂ [ No CAS ]
C₃₆H₅₈FN₅O₁₀ [ No CAS ]

Reference： [1]Patent: WO2018/201076,2018,A2 .Location in patent: Paragraph 00329

16
[ 612511-81-6 ]
2-(6-((2S,5S)-2,5-dimethylpyrrolidin1-yl)pyridin-3-yl)-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-benzo[d]imidazole [ No CAS ]