Home Cart Sign in  
Chemical Structure| 444731-72-0 Chemical Structure| 444731-72-0

Structure of 444731-72-0

Chemical Structure| 444731-72-0

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 444731-72-0 ]

CAS No. :444731-72-0
Formula : C9H11N3
M.W : 161.20
SMILES Code : NC1=CC2=NN(C)C(C)=C2C=C1
MDL No. :MFCD09258896
InChI Key :PVNVSSNARYHLRF-UHFFFAOYSA-N
Pubchem ID :11542827

Safety of [ 444731-72-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 444731-72-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 9
Fraction Csp3 0.22
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 50.37
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

43.84 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.44
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.29
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.47
Log Po/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.

1.16
Log Po/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

1.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.3

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.21
Solubility 1.0 mg/ml ; 0.00621 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.81
Solubility 2.49 mg/ml ; 0.0155 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-2.49
Solubility 0.522 mg/ml ; 0.00324 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

Yes
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

Yes
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.

-6.37 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

1.0 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)

1.54

Application In Synthesis of [ 444731-72-0 ]

* 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.

  • Downstream synthetic route of [ 444731-72-0 ]

[ 444731-72-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 6494-19-5 ]
  • [ 444731-72-0 ]
YieldReaction ConditionsOperation in experiment
96.7% With ammonium formate;palladium 10% on activated carbon; In methanol; water; at 25 - 30℃; for 6h; Procedure 2: A 2-L 3-necked round bottom flask was fitted with nitrogen inlet and outlet and with mechanical stirring. A moderate nitrogen flow was initiated and the reactor was charged with 10percent Pd/C (50percent water wet, 6.0 g). Stirring was initiated and the reactor was charged with methanol (750 mL) and the product of Intermediate Example 1 (50 g). Ammonium formate (82.54 g) was dissolved in water (120 mL). The water solution of ammonium formate was added to the reaction solution at an addition rate, which kept the reaction temperature at or between 25 and 30° C. The reaction was allowed to proceed at 25° C. After 6 h the reaction was judged to be finished based on HPLC analysis. The mixture was filtered and the catalyst washed with methanol (50 mL). The methanol layers were combined and the solvent removed under reduced pressure. The residue was dissolved in water (200 mL) and was extracted with methylene chloride (3*250 mL). The methylene chloride layers were combined and solvent removed under vacuum to remove approximately half the solvent. Heptane (400 mL) was added and the vacuum distillation continued until approximately 300 mL reaction product slurry remained. The product was isolated by filtration and dried under vacuum at 50° C. for 4 h. to yield 2,3-dimethyl-6-amino-2H-indazole as the free base. (40.76 g, 96.7percent). 1H NMR (300 MHz, DMSO-d6) delta 7.31 (d, J=8.9 Hz, 1H), 6.45 (d, J=8.9 Hz, 1H), 6.38 (s, 1H), 4.95 (s, br, 2H), 3.85 (s, 3H), 2.44 (s, 3H) MS (ES+, m/z) 162 (M+H).
  • 2
  • [ 50-00-0 ]
  • [ 444731-72-0 ]
  • [ 1376676-65-1 ]
YieldReaction ConditionsOperation in experiment
37.1% Sodium methoxide (1.8g, 33.3mmol) in anhydrous methanol (60mL) solution,obtained in Example 1 was added at once 2,3-dimethyl--2H- indazol-6-amine(1.6g, 10mmol), stirring at room temperature was added paraformaldehyde (0.6g,20mmol), the reaction was refluxed for 2h, stirring continued at roomtemperature 2h, temperature was lowered to 0 C, 10 C or less, in themixture was added portionwise NaBH 4 (0.76g, 20mmol) , 40 C reaction 3h, thecrude oil was cooled to room temperature and stirring was continued overnight,concentrated to remove methanol, aqueous layer was extracted with ethylacetate, the organic layer was washed with water, dried over anhydrous sodiumsulfate, filtered, and concentrated to yield. A silica gel column (methylenechloride: methanol = 20: 1) to give a white solid 0.65g, yield 37.1%.
Sodium methoxide (19 gm) was dissolved in methanol (610 ml) and then added 2,3-dimethyl-2H-indazol-6-amine (13 gm). The reaction mixture was stirred for 15 minutes and then added paraformaldehyde (3.9 gm). The contents were heated to 60C and stirred for 10 hours. The reaction mass was then cooled to room temperature and maintained for 4 hours 30 minutes. Sodium borohydride (2.8 gm) was added to the reaction mass slowly at room temperature and then heated to reflux. The reaction mass was maintained for 2 hours at reflux and then cooled to room temperature. The reaction mass was stirred for 14 hours at room temperature and then added sodium hydroxide solution (1M, 100 ml). The pH of the reaction mass was adjusted to 8.0 to 8.5 with hydrochloric acid solution (40 ml) and then added ethyl acetate (400 ml). Then the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate and treated with carbon. The combined organic layers were washed with sodium chloride solution and dried with sodium sulfate. The organic layer was treated with carbon and filtered through hi-flow bed. The solvent was distilled off under vacuum at below 50C to obtain a residual mass. To the residual mass was added diisopropyl ether (75 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 10 gm of N,2,3-trimethyl-2H-indazol-6-amine.
10 g Sodium methoxide (19 gm) was dissolved in methanol (610 ml) and then added 2,3-dimethyl-2H-indazol-6-amine (13 gm). The reaction mixture was stirred for 15 minutes and then added paraformaldehyde (3.9 gm). The contents were heated to 60 C. and stirred for 10 hours. The reaction mass was then cooled to room temperature and maintained for 4 hours 30 minutes. Sodium borohydride (2.8 gm) was added to the reaction mass slowly at room temperature and then heated to reflux. The reaction mass was maintained for 2 hours at reflux and then cooled to room temperature. The reaction mass was stirred for 14 hours at room temperature and then added sodium hydroxide solution (1M, 100 ml). The pH of the reaction mass was adjusted to 8.0 to 8.5 with hydrochloric acid solution (40 ml) and then added ethyl acetate (400 ml). Then the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate and treated with carbon. The combined organic layers were washed with sodium chloride solution and dried with sodium sulfate. The organic layer was treated with carbon and filtered through hi-flow bed. The solvent was distilled off under vacuum at below 50 C. to obtain a residual mass. To the residual mass was added diisopropyl ether (75 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 10 gm of N,2,3-trimethyl-2H-indazol-6-amine.
  • 6
  • [ 444731-72-0 ]
  • [ 6973-09-7 ]
  • [ 530-62-1 ]
  • N-(2,3-dimethyl-2H-indazol-6-yl)-N'-(3-sulfamoyl-4-methylphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.8% 2- Methyl-5-amino-benzenesulfonamide (1.86g, 10mmol) in drydichloromethane (20 mL) was added CDI (1.62g, 10mmol), under nitrogen at roomtemperature the reaction 3h, Example 1 was slowly added dropwise the obtained2,3-dimethyl--2H- indazol-6-amine (1.61g, 10mmol) in dichloromethane (10 mL)solution was reacted at room temperature 3h. Cooled to 10 ° C, suctionfiltered, washed with dichloromethane (10mL × 2), recrystallized from ethanolto give 1.86 g of an off-white solid, yield 49.8percent.
  • 7
  • [ 67-56-1 ]
  • [ 444731-72-0 ]
  • [ 1376676-65-1 ]
YieldReaction ConditionsOperation in experiment
94% With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; The compound of formula 7,Triphenylphosphine, methylene chloride and dichlorodicyanobenzoquinone were added to the reaction flask.Methanol was added dropwise to the reaction solution. After the reaction was completed, an aqueous sodium thiosulfate solution was added and the layers were separated. The organic phase was washed with saturated brine.Then, methanol was added and it was reduced to 0 degree. After stirring for 1-2 hours, the solid was precipitated as a compound of Formula 2, with a yield of 94%
  • 8
  • [ 444731-72-0 ]
  • [ 444731-75-3 ]
  • C23H24N8*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
41.6% With hydrogenchloride; In isopropyl alcohol; for 4h;Reflux; To a 100 mL round-bottom flask was charged IM2 (1.1 g, 3.8 mmol), SM1 (0.75 g, 3.8 mmol), 1 ml conc HCl and isopropanol (50 mL). The mixture was stirred at reflux for 4 h then cooled to room temperature and the resultant precipitate was collected by filtration and successfully washed with water and ethanol. Recrystallized from EtOH/H2O to yield impurity II (0.65 g, 41.6 %) as a brown solid. 1H NMR (600 MHz, DMSO-d6) (delta, ppm): 10.77 (s, 1H), 7.94(s, 1H), 7.84 - 7.88 (m, 2H), 7.63 (d, J = 8.6Hz, 1H), 7.59 (s, 1H), 7.06 (d, J = 8.7 Hz, 1H), 6.94 - 6.96 (m, 1H), 5.89(s, 1H), 4.08 (s, 3H), 4.02 (s, 3H), 3.58 (s, 3H), 2.65 (s, 3H), 2.58 (s, 3H). 13C NMR (600 MHz,DMSO-d6) (delta, ppm): 162.6, 150.9, 146.2, 143.4, 142.7, 140.5, 137.6, 137.2, 134.2, 123.4, 122.2, 120.5, 119.0, 117.7, 117.6, 114.1, 103.6, 97.9, 40.1, 37.8, 37.1, 9.86, 9.81; HRMS m/z calcd for C23H25N8 [M+H]+ 427.2353, found 427.2348.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 444731-72-0 ]

Amines

Chemical Structure| 635702-60-2

A181727 [635702-60-2]

2,3-Dimethyl-2H-indazol-6-amine hydrochloride

Similarity: 0.98

Chemical Structure| 5228-52-4

A665575 [5228-52-4]

5-Amino-2-ethyl-2H-indazole

Similarity: 0.95

Chemical Structure| 221681-92-1

A282549 [221681-92-1]

1,3-Dimethyl-1H-indazol-6-amine

Similarity: 0.92

Chemical Structure| 50593-30-1

A370196 [50593-30-1]

2-Methyl-2H-indazol-6-amine

Similarity: 0.90

Chemical Structure| 1105187-46-9

A270250 [1105187-46-9]

2-(5-Amino-2H-indazol-2-yl)ethanol

Similarity: 0.88

Related Parent Nucleus of
[ 444731-72-0 ]

Indazoles

Chemical Structure| 635702-60-2

A181727 [635702-60-2]

2,3-Dimethyl-2H-indazol-6-amine hydrochloride

Similarity: 0.98

Chemical Structure| 5228-52-4

A665575 [5228-52-4]

5-Amino-2-ethyl-2H-indazole

Similarity: 0.95

Chemical Structure| 221681-92-1

A282549 [221681-92-1]

1,3-Dimethyl-1H-indazol-6-amine

Similarity: 0.92

Chemical Structure| 50593-30-1

A370196 [50593-30-1]

2-Methyl-2H-indazol-6-amine

Similarity: 0.90

Chemical Structure| 1105187-46-9

A270250 [1105187-46-9]

2-(5-Amino-2H-indazol-2-yl)ethanol

Similarity: 0.88