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Chemical Structure| 66247-84-5 Chemical Structure| 66247-84-5

Structure of 66247-84-5

Chemical Structure| 66247-84-5

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Product Details of [ 66247-84-5 ]

CAS No. :66247-84-5
Formula : C4H8ClN3
M.W : 133.58
SMILES Code : Cl[H].NCC1=CNC=N1
MDL No. :MFCD13176517
InChI Key :MPLLIZRHKYQLDU-UHFFFAOYSA-N
Pubchem ID :45791344

Safety of [ 66247-84-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 66247-84-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 5
Fraction Csp3 0.25
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 33.23
TPSA ?

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

54.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

-0.24
Log Po/w (WLOGP)?

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

0.52
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.

-0.94
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

0.66
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.0

Water Solubility

Log S (ESOL):?

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

-0.91
Solubility 16.3 mg/ml ; 0.122 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.

-0.45
Solubility 47.3 mg/ml ; 0.354 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

-1.2
Solubility 8.49 mg/ml ; 0.0635 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.

-7.29 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

2.0
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)

1.51

Application In Synthesis of [ 66247-84-5 ]

* 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 [ 66247-84-5 ]

[ 66247-84-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 57090-90-1 ]
  • [ 66247-84-5 ]
  • 2
  • [ 66247-84-5 ]
  • [ 132757-24-5 ]
  • (2S,3R)-3-tert-Butoxy-3-(1H-imidazol-4-yl)-2-[(6-[(Z)-3H-imidazol-4-ylmethylimino]-methyl}-4-methoxy-pyridine-2-carbonyl)-amino]-propionic acid tert-butyl ester [ No CAS ]
  • 3
  • [ 191104-34-4 ]
  • [ 66247-84-5 ]
  • 4
  • [ 3034-50-2 ]
  • [ 66247-84-5 ]
YieldReaction ConditionsOperation in experiment
100% 12.0 g (124 mmol) 4-formyl-imidazole are placed together with 750 mg Raney nickel in 1000 ml of methanolic ammonia solution and shaken at 40° C. for 30 min. Then the mixture is hydrogenated in a Parr apparatus under a hydrogen atmosphere at 5 bars pressure at 40° C. for 14 h. Another 750 mg Raney nickel are then added and the mixture is again hydrogenated at 50° C. under a hydrogen atmosphere at 5 bars pressure for 14 h. The mixture is filtered, evaporated down i. vac., and in each case methanol, toluene and ethanol are added to the residue and it is again evaporated down completely i. vac. The residue is combined with ethereal hydrochloric acid in methanol and evaporated down completely i. vac. The residue is in each case combined with methanol and dichloromethane and evaporated down completely i. vac.Yield: 21.2 g (quant.)Rt value: 0.49 min (D)C4H7N3*2 HCl (170.04/97.12)Mass spectrum: (M+H)+=98
  • 5
  • [ 771-50-6 ]
  • [ 66247-84-5 ]
  • N-[(1H-Imidazol-4-yl)methyl]-1H-indole-3-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; triethylamine; In methanol; 1,2-dichloro-ethane; acetonitrile; EXAMPLE 1 N-[(1H-Imidazol-4-yl)methyl]-1H-indole-3-carboxamide hydrochloride A suspension of indole-3-carboxylic acid (0.592 g) and thionyl chloride (0.6 ml) in 1,2-dichloroethane (50 ml) was stirred at room temperature for 60h under nitrogen. The suspension was evaporated in vacuo and further 1,2-dichloroethane (50 ml) was added. The suspension was re-evaporated to give a solid (0.6 g) which was dissolved in acetonitrile (25 ml) and triethylamine (5 ml), and added to a stirred suspension of <strong>[66247-84-5]imidazole-4-methanamine dihydrochloride</strong> (0.684 g) and triethylamine (5 ml) in acetonitrile (25 ml) at -5° under nitrogen. The reaction was stirred for 1h while warming to room temperature and then heated at reflux for 20h. The mixture was evaporated in vacuo, dissolved in methanol (20 ml) and partitioned between hydrochloric acid (0.2N; 2*200 ml) and dichloromethane (2*100 ml). The combined aqueous layers were basified with saturated potassium carbonate and extracted with chloroform (3*150 ml). The combined chloroform layers were dried and evaporated in vacuo to give a semi-solid which was triturated with ether to give a solid (0.24 g). This was adsorbed onto silica and purified by FCC eluding with System A (83.5:151.5) to give a solid (ca. 50 mg) which was dissolved in methanol (3 ml) and acidified with ethanolic hydrogen chloride. Dry ether (20 ml) was added until the solution turned cloudy, precipitating the title compound (26 mg), m.p. 225°-229° (decomp.). Analysis Found: C,55.1; H,4.7; N,19.5; C13 H12 N4 O. HCl. 0.38H2 O requires C,55.1; H,4.5; N,19.5percent
  • 6
  • [ 1076192-10-3 ]
  • [ 66247-84-5 ]
  • [ 1076192-11-4 ]
YieldReaction ConditionsOperation in experiment
50% With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h; To the previous mixture containing intermediate a115 (0.44 g, 1.15 mmol, 73 wt percent) is added (1 /-/-imidazol-4-ylmethyl)amine dihydrochloride (0.59 g, 3.46 mmol, 3 eq) [from A. Turner et al., J. Am. Chem. Soc. (1949), 71 , 2801-2803.], and anhydrous cesium carbonate (1.88 g, 5.76 mmol, 5 eq) in dry DMF (15 ml_). The mixture is vigorously stirred at 60 0C for 3 h. The reaction mixture is cooled, concentrated under reduced pressure, diluted with water, and subjected to extraction with ethyl acetate (three times). The combined organic extracts are washed with brine, dried over anhydrous Na2SC>4, and evaporated. The residue (0.35 g) is purified by chromatography on silicagel (gradient CHCI3/MeOH from 20/1 to 10/1 v/v) to afford 5-chloro-2-(1 H-imidazol-4-ylmethyl)-1 ,4- dihydroisoquinolin-3(2H)-one 53 (0.15 g). Yield: 50 percent. LC-MS (MH+): 262/264.
  • 7
  • [ 66247-84-5 ]
  • [ 129451-79-2 ]
  • [ 1093660-15-1 ]
  • 8
  • [ 1225591-94-5 ]
  • [ 66247-84-5 ]
  • [ 1225653-10-0 ]
YieldReaction ConditionsOperation in experiment
63% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃; for 2h; 78-2 Methyl (S)-2-[3-(1H-imidazol-4-yl-methyl)ureido]-3-(4-methoxyphenyl)- propanoate; 1 .1 g (0.37 mmol) of methyl (S)-3-(4-methoxyphenyl)-2-(4-nitrophenoxycarbonyl- amino)propanoate (cf. preparation 2-2) and 0.7 mL (0.37 mmol) of diisopropyl- ethylamine in 5 mL of dimethylformamide are added at 800C to a solution of 500 mg (0.37 mmol) of C-(1 H-imidazol-4-yl)methylamine dihydrochloride in 15 mL of dimethylformamide. The reaction mixture is stirred for 2 hours at 800C. The reaction is stopped by adding 30 ml. of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (eluent: 80/20 dichloromethane/methanol). 279 mg of methyl (S)-2-[3-(1 H-imidazol-4-yl-methyl)- ureido]-3-(4-methoxyphenyl)propanoate in the form of a yellow oil are obtained in a yield of 63percent.
  • 9
  • [ 1225653-08-6 ]
  • [ 66247-84-5 ]
YieldReaction ConditionsOperation in experiment
29% With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; ethanol; ethyl acetate; at 80℃; under 4500.45 Torr; for 3h; 18-1-3 C-(1 H-lmidazol-4-yl)methylamine dihydrochloride; To a solution containing 450 mg of piperidin-1 -yl-(1 -trityl-1 H-imidazol-4-yl- methylene)amine in 3.5 mL of 3N hydrogen chloride in ethyl acetate are added 90 mg of 10percent Pd/C, 0.5 mL of THF and 0.9 mL of ethanol. The reaction medium is placed under a hydrogen pressure of 6 bar and heated at 80°C for 3 hours. After filtering off the catalyst and evaporating off the solvents, the crude product obtained is chromatographed on silica gel (eluent: 6/4 DCIWMeOH). 50 mg of C-(1 H-imidazol- 4-yl)methylamine dihydrochloride in the form of a white powder are obtained in a yield of 29percent.
  • 10
  • 4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)benzaldehyde [ No CAS ]
  • [ 66247-84-5 ]
  • N-((1H-imidazol-4-yl)methyl)-1-(4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)phenyl)methanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Example 119A N-((1H-imidazol-4-yl)methyl)-1-(4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)phenyl)methanamine [1125] To a suspension of <strong>[66247-84-5]1H-imidazol-4-ylmethylamine dihydrochloride</strong> (269 mg, 1.59 mmol) in a mixture of dichloromethane (3 mL) and methanol (1 mL) was added triethylamine (0.442 mL, 3.17 mmol). After stirring the mixture for five minutes, Example 105B (125 mg, 0.317 mmol) and acetic acid (0.181 mL, 3.17 mmol) were added. The mixture was heated at 50° C. for 1 hour. The mixture was cooled in an ice bath and sodium triacetoxyborohydride (134 mg, 0.634 mmol) was added portionwise over several minutes. After 15 minutes, the ice bath was removed and the reaction mixture was stirred 2 hours while warming to ambient temperature. The reaction mixture was quenched with 1 M sodium hydroxide (2 mL) and partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-10percent 7N methanolic ammonia in methylene chloride) to provide the title compound (90.3 mg, 62percent yield).
  • 11
  • 2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile [ No CAS ]
  • [ 66247-84-5 ]
  • 2-(((1H-imidazol-4-yl)methyl)amino)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.6% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 100℃; for 16h; N,N-Diisopropylethylamine (0.24 mL, 1.389 mmol) was added to 2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 4 (105.8 mg, 0.278 mmol) in 1,4-dioxane (1.3 mL) and dimethyl sulfoxide (1.3 mL) at room temperature, followed by<strong>[66247-84-5](1H-imidazol-4-yl)methanamine dihydrochloride</strong> 5d (71 mg,0.417 mmol) and the solution was heated to 100 °C and stirred forsixteen hours. The reaction mixture was poured into ether, washed with water, dried over magnesium sulfate, filtered, and concentrated.The residue was purified by silica gel chromatography,eluting with methanol:ethyl acetate (1:24) to give 2-(((1H-imidazol-4-yl)methyl)amino)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 6d (73.1 mg, 0.157 mmol, 56.6percentyield). 1H NMR (400 MHz, CD3SOCD3) d 11.82 (br s, 0.6H), 11.71(br s, 0.4H), 8.38?8.14 (m, 2H), 8.02?7.92 (m, 1H), 7.70?6.80 (m,7H), 4.86?4.68 (m, 2H), 4.51 (d, 0.8H, J = 6 Hz), 4.45 (d, 1.2H, J = 6Hz); LC?MS (LC?ES) M+H = 442.
  • 12
  • [ 728034-12-6 ]
  • [ 66247-84-5 ]
  • [ 165806-95-1 ]
  • 4-(1-((1H-imidazol-4-yl)methyl)-4-(4-fluorophenyl)-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used
 

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[ 66247-84-5 ]

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