423768-52-9|3-(Aminomethyl)-1,5-dimethylpyrazole| Ambeed

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Quality Control of [ 423768-52-9 ] Purity: 97% SDS Specification

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Product Details of [ 423768-52-9 ]

CAS No. :	423768-52-9
Formula :	C₆H₁₁N₃
M.W :	125.17
SMILES Code :	NCC1=NN(C)C(C)=C1
MDL No. :	MFCD03422531
InChI Key :	JGYXJOBBROGMLL-UHFFFAOYSA-N
Pubchem ID :	2776367

Safety of [ 423768-52-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 423768-52-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	5
Fraction Csp3	0.5
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	36.13
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.48
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.04
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.16
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.67
Solubility	27.1 mg/ml ; 0.216 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	0.02
Solubility	130.0 mg/ml ; 1.04 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.19
Solubility	8.14 mg/ml ; 0.065 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.4 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.63

Application In Synthesis of [ 423768-52-9 ]

* 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 [ 423768-52-9 ]

[ 423768-52-9 ] Synthesis Path-Downstream 1~21

1
[ 423768-52-9 ]
[ 872423-48-8 ]
C₂₉H₃₁N₄O₂P [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 11488 - 11500.

2
[ 423768-52-9 ]
[ 872423-49-9 ]
(1R,2R)-2-((R)-diphenylphosphinylamino)phenyl(methyl)cyclopropane carboxylic acid (1,5-dimethyl-1H-pyrazol-3-ylmethyl)amide [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 11488 - 11500.

3
[ 423768-52-9 ]
[ 4774-14-5 ]
2-[(1,5-dimethyl-1H-pyrazol-3-yl)methylamino]-6-chloropyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 407 - 416.

4
[ 423768-52-9 ]
[ 1027039-32-2 ]
[ 950598-91-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4538 - 4544.

5
[ 423768-52-9 ]
2-[(1,5-dimethyl-1H-pyrazol-3-yl)methylamino]-6-(3-acetamidophenyl)pyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 407 - 416.

6
[ 423768-52-9 ]
[ 75-44-5 ]
[ 1034257-10-7 ]
[ 1034257-58-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2990 - 2995.

7
[ 423768-52-9 ]
[ 1203605-21-3 ]
[ 1203604-47-0 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium carbonate; In acetonitrile; at 85℃;Inert atmosphere;	Under argon, a solution of 3-chloro-5-(2,6-dimethoxyphenyl)-1,2,4-triazine (6.85 mg, 0.027 mmol, prepared as in example 41), <strong>[423768-52-9](1,5-dimethyl-1H-pyrazol-3-yl)methylamine</strong> (8 mg, 0.064 mmol) and potassium carbonate (3.8 mg, 0.028 mmol) in anhydrous acetonitrile (0.7 mL) was stirred at 85C overnight. The solution was evaporated. The residue was purified by preparative TLC (silica gel, dichloromethane/methanol 95/5) to afford 5-(2,6-dimethoxyphenyl)-N-[(1,5-dimethyl-1H-pyrazol-3-yl)methyl]-1,2,4-triazin-3-amine (5.5 mg, 59%) as an off-white solid. ESI-MS m/z 341 (M+H)+. 1H NMR (CDCl3), delta (ppm): 8.45 (s, 1H), 7.40 (t, J = 8.4 Hz, 1H), 6.64 (d, J = 8.4 Hz, 2H), 6.06 (s, 1H), 4.70 (d, J = 5.2 Hz, 2H), 3.77 (s, 6H), 3.73 (s, 3H), 2.23 (s, 3H).

References: [1]Patent: EP2141164,2010,A1 .Location in patent: Page/Page column 40-41.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1418 - 1430.

8
[ 5744-59-2 ]
[ 423768-52-9 ]

References: [1]Patent: WO2009/139834,2009,A1 .

9
[ 54384-74-6 ]
[ 423768-52-9 ]

Yield	Reaction Conditions	Operation in experiment
31%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Reflux;	To the above product (5 g, 35.97 mmol) in THF (70 mL) was added LiAlH4 (4.1 g, 107.89 mmol) in several batches at 00C. The resulting solution was refluxed for 1 hr. The solids were filtered out and the filtrate was concentrated, resulted in 3 g (67%) of 1,5- dimethyl-lH-pyrazol-3-yl)methanamine as yellow oil.

References: [1]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 129.

10
[ 423768-52-9 ]
[ 1196886-61-9 ]

References: [1]Patent: WO2009/139834,2009,A1 .

11
[ 423768-52-9 ]
[ 1196882-72-0 ]

References: [1]Patent: WO2009/139834,2009,A1 .

12
[ 423768-52-9 ]
[ 1196886-63-1 ]

References: [1]Patent: WO2009/139834,2009,A1 .

13
[ 423768-52-9 ]
[ 1196882-74-2 ]

References: [1]Patent: WO2009/139834,2009,A1 .

14
[ 423768-52-9 ]
[ 848694-76-8 ]
[ 1196886-59-5 ]

Yield	Reaction Conditions	Operation in experiment
31%	With triethylamine; In ethanol; for 3h;Reflux;	To a solution of ethyl 2-(2-amino-4,6-dichloropyrimidin-5-yl)acetate (200 mg, 0.80 mmol) in EtOH (30 mL) was added (l,5-dimethyl-lH-pyrazol-3-yl)methanamine (300 mg, 2.40 mmol) and Et3N (400 mg, 3.96 mmol). The resulting solution was refluxed for 3 hours. The reaction mixture was concentrated under vacuum. The residue was purified on a silica gel column with DCMrMeOH (50:1), resulted in 0.25 g (31%) of ethyl 2-(2-amino-4-chloro- 6-((l,5-dimethyl-lH-pyrazol-3-yl) methylamino)pyrimidin-5-yl)acetate as a yellow solid

References: [1]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 129.

15
[ 423768-52-9 ]
[ 1393598-51-0 ]
[ 1393598-41-8 ]

References: [1]ACS Combinatorial Science,2012,vol. 14,p. 491 - 495.

16
[ 423768-52-9 ]
[ 10035-16-2 ]
[ 1185322-46-6 ]

Yield	Reaction Conditions	Operation in experiment
63%		To a solution of benzofuran-5-carbaldehyde (526 mg, 3.6 mmol, 1.2 equiv) in MeOH (15 mL) were added NaOAc (246 mg, 3.0 mmol, 1.0 equiv), HOAc (172 muL, 3.0 mmol, 1.0 equiv) and (l,5-dimethyl-l-pyrazole-3-yl)methylamine (376 mg, 3.0 mmol, 1.0 equiv., available from Maybridge). The mixture was stirred at room temperature for 5 min, and then treated with NaBH4 (273 mg, 7.2 mmol, 2.4 equiv) at 0 0C. The resulting mixture <n="52"/>was allowed to return to room temperature and stirred for 1 h, after which time the reaction was quenched with IN NaOH. The mixture was concentrated in vacuo to remove most of the MeOH, and the water layer was extracted with ethyl acetate three times. The combined organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica gel with ethyl acetate/dichloromethane/methanol 5/5/1 as eluant to afford l-(Benzofuran-5-yl)-N-((l,5-dimethyl-lH-pyrazol-3-yl)methyl)methanamine (478 mg, 63%). MS 256 (MH)+. Purity 95% (HPLC)

References: [1]Patent: WO2009/105776,2009,A1 .Location in patent: Page/Page column 50-51.

17
[ 423768-52-9 ]
[ 1007876-34-7 ]

References: [1]Patent: WO2009/105776,2009,A1 .

18
[ 423768-52-9 ]
[ 1185321-73-6 ]

References: [1]Patent: WO2009/105776,2009,A1 .

19
[ 423768-52-9 ]
C₁₅H₁₆ClN₃O₂ [ No CAS ]
C₂₁H₂₆N₆O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4477 - 4481.

20
[ 423768-52-9 ]
C₁₅H₁₆ClN₃O₃ [ No CAS ]
C₂₁H₂₆N₆O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4477 - 4481.

21
[ 423768-52-9 ]
C₁₄H₁₃ClFN₃O₂ [ No CAS ]
C₂₀H₂₃FN₆O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4477 - 4481.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 423768-52-9 ]

Amines

A780921 [28466-21-9]

1,3,5-Trimethyl-1H-pyrazol-4-amine

Similarity: 0.91

A291648 [1185303-62-1]

4-Amino-1,3,5-trimethylpyrazole hydrochloride

Similarity: 0.89

A906897 [612511-81-6]

(1-Methyl-1H-pyrazol-3-yl)methanamine

Similarity: 0.80

A179536 [947763-34-0]

1-Ethyl-3-methyl-1H-pyrazol-4-amine

Similarity: 0.80

A717465 [852227-87-3]

1-(1,3-Dimethyl-1H-pyrazol-5-yl)-N-methylmethanamine

Similarity: 0.79

Related Parent Nucleus of
[ 423768-52-9 ]

Pyrazoles

A780921 [28466-21-9]

1,3,5-Trimethyl-1H-pyrazol-4-amine

Similarity: 0.91

A433627 [1072-91-9]

1,3,5-Trimethylpyrazole

Similarity: 0.90

A291648 [1185303-62-1]

4-Amino-1,3,5-trimethylpyrazole hydrochloride

Similarity: 0.89

A470610 [25016-09-5]

1,3-Dimethyl-1H-pyrazole-5-carbaldehyde

Similarity: 0.81

A906897 [612511-81-6]

(1-Methyl-1H-pyrazol-3-yl)methanamine

Similarity: 0.80

Precautionary Statements-General
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Physical hazards
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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H242	Heating may cause a 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
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

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CAS No.: 423768-52-9

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