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Structure of 7126-38-7

Chemical Structure| 7126-38-7

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Product Details of [ 7126-38-7 ]

CAS No. :7126-38-7
Formula : C5H4N2
M.W : 92.10
SMILES Code : N#CC1=CNC=C1
MDL No. :MFCD00967073
InChI Key :PCYWMDGJYQAMCR-UHFFFAOYSA-N
Pubchem ID :564206

Safety of [ 7126-38-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 7126-38-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 25.51
TPSA ?

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

39.58 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.04
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

0.43
Log Po/w (WLOGP)?

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

0.89
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.

-0.56
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

1.43
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.65

Water Solubility

Log S (ESOL):?

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

-1.21
Solubility 5.67 mg/ml ; 0.0616 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.

-0.83
Solubility 13.7 mg/ml ; 0.148 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

-1.6
Solubility 2.31 mg/ml ; 0.0251 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

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.

-6.56 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)

1.34

Application In Synthesis of [ 7126-38-7 ]

* 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 [ 7126-38-7 ]

[ 7126-38-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 105629-96-7 ]
  • [ 7126-38-7 ]
  • 2
  • [ 52162-55-7 ]
  • [ 7126-38-7 ]
  • 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)pyrrole-3-carbonitrile [ No CAS ]
  • 3
  • [ 117610-34-1 ]
  • [ 7126-38-7 ]
  • [ 140614-06-8 ]
  • 4
  • [ 7126-38-7 ]
  • [ 65018-89-5 ]
  • [ 127486-48-0 ]
  • [ 140614-00-2 ]
  • [ 140614-01-3 ]
  • 5
  • [ 7126-38-7 ]
  • [ 97744-99-5 ]
  • 6
  • [ 7126-38-7 ]
  • [ 97744-98-4 ]
  • 7
  • [ 40740-39-4 ]
  • [ 7126-38-7 ]
  • 8
  • [ 80242-24-6 ]
  • [ 7126-38-7 ]
  • 9
  • [ 80242-24-6 ]
  • [ 124-38-9 ]
  • [ 7126-38-7 ]
  • 10
  • Benzenesulfonyl-(1H-pyrrol-3-yl)-methanone oxime [ No CAS ]
  • [ 7126-38-7 ]
  • 11
  • (E/Z)-N-(3-Cyanopropyliden)asparaginsaeuredinitril [ No CAS ]
  • [ 100-70-9 ]
  • [ 100-54-9 ]
  • [ 26187-27-9 ]
  • [ 7126-38-7 ]
  • 12
  • (E/Z)-N-(3-Cyanopropyliden)asparaginsaeuredinitril [ No CAS ]
  • [ 100-70-9 ]
  • [ 100-54-9 ]
  • [ 26187-27-9 ]
  • [ 7126-38-7 ]
  • [ 23974-91-6 ]
  • 13
  • [ 87022-42-2 ]
  • [ 107-13-1 ]
  • [ 7126-38-7 ]
  • 15
  • [ 3601-89-6 ]
  • [ 7126-38-7 ]
  • [ 110089-37-7 ]
  • 16
  • [ 852510-45-3 ]
  • [ 7126-38-7 ]
  • 1-{3-[4-(3-chloro-phenyl)-1-methyl-2-oxo-1,2-dihydro-quinolin-6-ylmethyl]-3<i>H</i>-imidazol-4-ylmethyl}-1<i>H</i>-pyrrole-3-carbonitrile [ No CAS ]
  • 19
  • [ 7126-38-7 ]
  • 1-(2'-deoxy-β-D-ribofuranosyl)-pyrrole-3-carboxamide-5'-triphosphate [ No CAS ]
  • 20
  • [ 7126-38-7 ]
  • [ 931-03-3 ]
  • 21
  • [ 80242-23-5 ]
  • [ 7126-38-7 ]
  • 22
  • [ 7126-38-7 ]
  • [ 110089-42-4 ]
  • 23
  • [ 7126-38-7 ]
  • [ 110089-40-2 ]
  • 24
  • [ 7126-38-7 ]
  • [ 110089-41-3 ]
  • 25
  • [ 369-34-6 ]
  • [ 7126-38-7 ]
  • [ 252336-89-3 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; 3-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene <strong>[7126-38-7]3-Cyanopyrrole</strong> (3.6 g, 39.1 mmol, CE Loader et al, Can. J. Chem., 1981, 59, 2673) and 3,4-difluoronitrobenzene (6.5 g, 40.9 mmol) were dissolved in DMF (50 ml) and cooled in an ice-bath. The mixture was stirred and sodium hydride (60percent in oil, 1.6 g, 40 mmol) added over 20 minutes. After allowing the mixture to come to ambient temperature, it was heated to 65° for 1 hour. Solvent was evaporated, the residue triturated with water, and filtered. The crude solide was purified by flash chromatography on silica, eluding with dichloromethane. Relevant fractions were combined to give the title product (3.75 g), mp 117-119°. MS (ESP): 230 (MH-) for C11H6FN3O2 NMR (CDCl3) delta: 6.68 (s, 1H); 7.09 (m, 1H); 7.61 (overlapping m, 2H); 8.20 (overlapping m, 2H).
  • 26
  • [ 7126-38-7 ]
  • [ 130511-58-9 ]
YieldReaction ConditionsOperation in experiment
With bromine; In dichloromethane; chloroform; EXAMPLE 12 Preparation of 2,4,5-Tribromo<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> STR23 To a stirred mixture of 1.50 g (16.3 mmol) of <strong>[7126-38-7]pyrrole-3-carbonitrile</strong> in 20 mL of chloroform is added dropwise from an addition funnel a mixture of 2.5 mL (48.5 mmol) of bromine in 7.5 mL of chloroform over about 30 minutes. The temperature of the mixture rises to 38° C. and a gummy solid is formed which necessitates addition of additional chloroform (25 mL) and some warming to achieve good stirring. The mixture is stirred an additional 2 hours at room temperature and the solid product is collected by filtration and washed with chloroform. The collected solids amount to 4.55 g. Concentration of the filtrate affords another 0.58 g of product. The combined solids are slurried with boiling methylene chloride. On cooling, filtration gives 3.66 g of a pale orange powder, mp 253°-255° C. Anal. Calcd for C5 HBr3 N2: C, 18.26; H, 0.31; N, 8.52; Br, 72.91. Found: C, 18.28; H, 0.35; N, 8.52; Br, 72.74.
With bromine; In dichloromethane; chloroform; EXAMPLE 18 Preparation of 2,4,5-Tribromo<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> STR24 To a stirred mixture of 1.50 g (16.3 mmol) of <strong>[7126-38-7]pyrrole-3-carbonitrile</strong> in 20 mL of chloroform is added dropwise from an addition funnel a mixture of 2.5 mL (48.5 mmol) of bromine in 7.5 mL of chloroform over about 30 minutes. The temperature of the mixture rises to 38° C. and a gummy solid is formed which necessitates addition of additional chloroform (25 mL) and some warming to achieve good stirring. The mixture is stirred an additional 2 hours at room temperature and the solid product is collected by filtration and washed with chloroform. The collected solids amount to 4.55 g. Concentration of the filtrate affords another 0.58 g of product. The combined solids are slurtied with boiling methylene chloride. On cooling, filtration gives 3.66 g of a pale orange powder, mp 253°-255° C. Anal. Calcd for C5 HBr3 N2: C, 18.26; H, 0.31; N, 8.52; Br, 72.91, Found: C, 18.28; H, 0.35; N, 8.52; Br, 72.74.
With bromine; In dichloromethane; chloroform; EXAMPLE 12 Preparation of 2,4,5-Tribromo<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> STR26 To a stirred mixture of 1.50 g (16.3 mmol) of <strong>[7126-38-7]pyrrole-3-carbonitrile</strong> in 20 mL of chloroform is added dropwise from an addition funnel a mixture of 2.5 mL (48.5 mmol) of bromine in 7.5 mL of chloroform over about 30 minutes. The temperature of the mixture rises to 38° C. and a gummy solid is formed which necessitates addition of additional chloroform (25 mL) and some warming to achieve good stirring. The mixture is stirred an additional 2 hours at room temperature and the solid product is collected by filtration and washed with chloroform. The collected solids amount to 4.55 g. Concentration of the filtrate affords another 0.58 g of product. The combined solids are slurried with boiling methylene chloride. On cooling, filtration gives 3.66 g of a pale orange powder, mp 253°-255° C. Anal. Calcd for C5 HBr3 N2: C, 18.26; H, 0.31; N, 8.52; Br, 72.91 Found: C, 18.28; H, 0.35; N, 8.52; Br, 72.74.
  • 27
  • [ 7126-38-7 ]
  • [ 130511-57-8 ]
YieldReaction ConditionsOperation in experiment
2.23 g (70%) With sulfuryl dichloride; In water; acetic acid; EXAMPLE 11 Preparation of 2,4,5-Trichloro<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> STR22 To a stirred mixture of 1.50 g (16.3 mmol) of <strong>[7126-38-7]pyrrole-3-carbonitrile</strong> in 50 mL of glacial acetic acid is added quickly dropwise 4.1 mL (51.0 mmol) of sulfuryl chloride by syringe through a rubber septum. With this addition the temperature of the reaction mixture rises from about 22° C. to 32° C. The mixture is stirred one and one-half hours and then diluted with 100 mL of water. The resulting solids are collected by filtration and washed with water. On drying, the yield is 2.23 g (70percent) of white solid, mp >300° C.
2.23 g (70%) With sulfuryl dichloride; In water; acetic acid; EXAMPLE 17 Preparation of 2,4,5-Trichloro<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> STR23 To a stirred mixture of 1.50 g (16.3 mmol) of <strong>[7126-38-7]pyrrole-3-carbonitrile</strong> in 50 mL of glacial acetic acid is added quickly dropwise 4.1 mL (51.0 mmo1) of sulfuryl chloride by syringe through a rubber septum. With this addition the temperature of the reaction mixture rises from about 22° C. to 32° C. The mixture is stirred one and one-half hours and then diluted with 100 mL of water. The resulting solids are collected by filtration and washed with water. On drying, the yield is 2.23 g (70percent) of white solid, mp >300° C.
  • 28
  • [ 130511-58-9 ]
  • [ 74-97-5 ]
  • [ 7126-38-7 ]
YieldReaction ConditionsOperation in experiment
46.7% With NaH; sodium ethanolate; In tetrahydrofuran; mineral oil; EXAMPLE 4 Preparation of 2,4,5-Tribromo-1-ethoxymethyl)pyrrole-3-carbonitrile STR7 A mixture of a 60percent dispersion of NaH in mineral oil (1.22 g, 0.0304 mol NaH) in tetrahydrofuran is treated dropwise with a solution of 2,4,5-tribromopyrrole-3-carbonitrile (10.0 g, 0.0304 mol) in tetrahydrofuran at 20° C. to 30° C. over a 20 minute period, stirred for 30 minutes at ambient temperatures, treated with bromochloromethane (11.80 g, 0.0912 mol) and solid sodium ethoxide (6.2 g, 0.0912 mol), heated at reflux temperature for 4 hours, cooled to room temperature, concentrated in vacuo and diluted with water and ethyl acetate. The organic phase is washed with water and brine, dried (Na2 SO4) and concentrated in vacuo to give a residue which is purified by flash chromatography (silica gel; ethyl acetate/heptane) to give the title compound as a white solid, 5.4 g (46.7percent yield), mp 139° C. to 143° C.
  • 29
  • [ 7126-38-7 ]
  • [ 74-88-4 ]
  • [ 130511-57-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride; In tetrahydrofuran; dichloromethane; water; acetic acid; EXAMPLE 11 Preparation of 2,4,5-Trichloro<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> STR22 To a stirred mixture of 1.50 g (16.3 mmol) of <strong>[7126-38-7]pyrrole-3-carbonitrile</strong> in 50 mL of glacial acetic acid is added quickly dropwise 4.1 mL (51.0 mmol) of sulfuryl chloride by syringe through a rubber septum. With this addition the temperature of the reaction mixture rises from about 22° C. to 32° C. The mixture is stirred one and one-half hours and then diluted with carbonitrile in 20 mL of dry THF over a 15 minute period. After 15 minutes, 0.50 mL (8.03 mmol) of methyl iodide is added dropwise by syringe over 10 minutes. Solids are formed and after stirring for about 3 hours, the mixture is diluted with 100 mL of water. The cloudy mixture is extracted twice with ethyl acetate and the combined organic layers washed successively with dilute NaOH, water, and saturated salt solution. After drying over magnesium sulfate, the organic mixture is filtered and concentrated in vacuo to give 0.99 g of an off-white solid. Purification by chromatography on silica gel using methylene chloride affords 0.68 g of yellow-white solid which is slurried with hexane and recovered by filtration; mp 110°-114° C. Anal. Calcd for C6 H3 Cl3 N2: C, 34.40; H, 1.44; N, 13 38; Cl, 50.78. Found: C, 34.25; H, 1.50; N, 13.36; Cl, 50.88.
  • 30
  • [ 50-00-0 ]
  • [ 7126-38-7 ]
  • [ 78758-78-8 ]
YieldReaction ConditionsOperation in experiment
With tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; water; at 20℃; for 0.5h; Reference Production Example 38 1-chloromethyl-3-cyano-1H-pyrole 670 mg of 3-cyano-1H-pyrole, 10 ml of tetrahydrofuran and 10 ml of formaldehyde 36 percent in water were mixed. 0.1 ml of tetrabutylammonium hydroxide 10 percent in water was added at room temperature, followed by stirring at room temperature for 30 minutes. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 1-hydroxymethyl-3-cyano-1H-pyrole.
  • 31
  • [ 274-87-3 ]
  • [ 504-29-0 ]
  • [ 4513-94-4 ]
  • [ 91028-12-5 ]
  • [ 7126-38-7 ]
  • 32
  • [ 5678-33-1 ]
  • [ 504-29-0 ]
  • [ 4513-94-4 ]
  • [ 91028-12-5 ]
  • [ 7126-38-7 ]
  • 33
  • [ 16544-33-5 ]
  • [ 4513-94-4 ]
  • [ 10479-84-2 ]
  • [ 24442-69-1 ]
  • [ 33555-85-0 ]
  • [ 91028-12-5 ]
  • [ 7126-38-7 ]
  • 2-ethynylcyclopropene [ No CAS ]
  • 34
  • 1,1-dimethylethyl 6-(3,4-dichlorophenyl)-1-([(methylsulfonyl)oxy]methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate [ No CAS ]
  • [ 7126-38-7 ]
  • C23H25Cl2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The example reported for derivatives 22/23 find general application for all the other N-linked heterocycles. Sodium hydride 60percent dispersed in mineral oil was added at 0 °C to a solution of 3-(trifluoromethyl)-1H-pyrazole in dry DMF. The mixture was stirred at this temperature for 15 min, then for an additional 5 min at room temperature. A solution of derivative 45 in dry DMF (2 ml) was then added and the mixture was stirred at 50 °C for 3 h 30 min. After cooling to RT, a saturated NH4Cl solution was added and the mixture was extracted with Et2O (2.x.). The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by Silica gel flash chromatography (gradient ethyl acetate in cyclohexane from 5 to 40percent) to give the intermediate BOC protected compound 22 and the intermediate BOC protected compound 23.
  • 35
  • [ 10296-29-4 ]
  • [ 4513-94-4 ]
  • [ 7126-38-7 ]
 

Historical Records

Technical Information

Categories

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[ 7126-38-7 ]

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[ 7126-38-7 ]

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