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Chemical Structure| 34667-88-4 Chemical Structure| 34667-88-4

Structure of 34667-88-4

Chemical Structure| 34667-88-4

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Product Details of [ 34667-88-4 ]

CAS No. :34667-88-4
Formula : C7H3FN2O2
M.W : 166.11
SMILES Code : N#CC1=CC=C([N+]([O-])=O)C=C1F
MDL No. :MFCD04038715

Safety of [ 34667-88-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 34667-88-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 39.94
TPSA ?

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

69.61 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.09
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

1.57
Log Po/w (WLOGP)?

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

2.03
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.

0.69
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

0.08
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.09

Water Solubility

Log S (ESOL):?

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

-2.16
Solubility 1.14 mg/ml ; 0.00687 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.

-2.64
Solubility 0.379 mg/ml ; 0.00228 mol/l
Class?

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

-2.14
Solubility 1.21 mg/ml ; 0.00731 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.

-6.2 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

2.0 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)

1.89

Application In Synthesis of [ 34667-88-4 ]

* 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 [ 34667-88-4 ]

[ 34667-88-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 150-19-6 ]
  • [ 34667-88-4 ]
  • 2-(3-Methoxy-phenoxy)-4-nitro-benzonitrile [ No CAS ]
  • 2
  • [ 34667-88-4 ]
  • [ 53312-80-4 ]
YieldReaction ConditionsOperation in experiment
100% Step A. Preparation of 4-amino-2-fluorobenzonitrile [00175] The mixture of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (8.31 g, 50 mmol) and tin (II) chloride dihydrate (56.4 g, 250 mmol) in 250 mL of EtOAc was stirred at 25 °C overnight. LCMS (78109-084) indicated the reaction was completed. 25 mL of sat. K2CO3 was added to the reaction. The resulting mixture was stirred at room temperature for 2h and was followed by addition of lOOg of solid K2CO3. The mixture was stirred at room temperature for 2 hours. Solid was removed by filtration and further washed with EtOAc (50 mLx2). The filtrate was concentrated to yield 6.81 g (100percent) of 4-amino-2-fluorobenzonitrile as an off white solid. 1H NMR (400 MHz, CDCl3) delta ppm 4.30 (s, 2 H) 6.29 - 6.51 (m, 2 H) 7.27 - 7.40 (m, 1 H). MS (ESI) 137 (M+H).
96% With iron; acetic acid; In ethyl acetate; for 2.0h;Heating / reflux; A mixture of <strong>[34667-88-4]4-nitro-2-fluorobenzonitrile</strong> (1.83 g, 5 mmol) and iron (1.68 g, 6 mmol) in a mixture of acetic acid (40 ml) and ethyl acetate (40 ml) was refluxed for 2 hours. The solid was filtered off and the filtrate was washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 95:5) to yield 4- amino-2-fluorobenzonitrile (54a) (0.653 g, 4.8 mmol, 96percent).
96% With hydrogen;palladium 10% on activated carbon; In ethanol; ethyl acetate; under 2585.81 Torr; for 1.0h; To <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (8.5 g, 51.2 mmol) was added 10percent palladium on carbon (0.5 g) and EtOAc (42.5 mL) and EtOH (170 mL) and the reaction was hydrogenated at 50 psi for 1 h. The reaction was filtered through Celite and the reaction mixture was concentrated to afford 6.7 g (96percent yield) as a light brown solid. LCMS m/z 135.1[M + H]+.
70% With palladium 10% on activated carbon; hydrogen; In methanol; for 3.0h; Reference Example 114 4-Amino-2-fluorobenzonitrile To a solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (2.51 g) in methanol (125 mL) was added 10percent palladium carbon (50percent containing water, 237 mg), and the mixture was stirred under a hydrogen atmosphere for 3 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) to give the title compound as a pale-yellow solid (yield 1.43 g, 70percent). 1H-NMR (CDCl3)delta: 4.31 (2H, brs), 6.37-6.45 (2H, m), 7.31-7.36 (1H, m).
palladium-carbon; In methanol; Reference Example 114 4-Amino-2-fluorobenzonitrile To a solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (2.51 g) in methanol (125 mL) was added 10percent palladium carbon (50percent containing water, 237 mg), and the mixture was stirred under a hydrogen atmosphere for 3 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) to give the title compound as a pale-yellow solid (yield 1.43 g, 70percent). 1H-NMR (CDCl3)delta: 4.31 (2H, brs), 6.37-6.45 (2H, m), 7.31-7.36 (1H, m).
With hydrogen;5%-palladium/activated carbon; In methanol; at 20℃; under 1500.15 Torr; for 2.0h; A solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (5 g, 30 mmol) in 300 mL methanol is stirred in a hydrogenation reactor with palladium (5percent on activated charcoal, 400 mg) for 2 h at RT and 2 bar hydrogen pressure. The reaction mixture is filtered and evaporated down. Yield: 4 g.
With iron; ammonium chloride; In ethanol; water; acetic acid; for 5.0h;Heating / reflux; Preparation 15: 4-Amino-2-fluorobenzonitrile: Saturated aqueous ammonium chloride (50 mL) and acetic acid (3 mL) were added to a stirred solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (50.0 g, 301 mmol) in EtOH (600 mL) followed by iron powder (2 g, 35.7 mmol). The mixture was heated under reflux and more iron powder (123 g, 2.20 mol) added portionwise over a 4 h period. The reaction heated for a further 1 h then allowed to cool to rt before being filtered through a celite plug. The filtrate was evaporated to dryness and the residual material partitioned between EtOAc (500 mL) and water (200 mL). The organic phase was washed with water (50 mL) and brine (100 mL), then dried (MgSO4) and evaporated to afford the title compound: deltaH (ddelta-DMSO) 6.41-6.46 (2H, m), 6.52 (2H, br s), 7.37- 7.41 (IH, m).
With palladium 10% on activated carbon; hydrogen; In ethanol; acetonitrile; under 2585.81 Torr; for 1.0h; <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (0.125 g, 0.751 mmol) was hydrogenated at 50 psi in the presence of 10percent Pd/C (40 mg) in EtOH/EtOAc (15mL) for 1 h. Filtered through Celite® and concentrated to an orange solid that was carried onto next step. MS (ESI) m/z: 137 (M+H)+.
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 12.0h; A solution of 66 6 (10.0g, 60.24mmol) in 69 methanol (100mL) was hydrogenated with 10percent 70 Pd/C (1.0g) under hydrogen atmosphere at room temperature for 12h. After filtration, the filtrate was evaporated to give the corresponding product. It was obtained as a gray 16 solid in 88percent yield. 7 was ready for the next step without the further purification. HRMS (ESI): m/z, calculated for C7H5FN2 137.0487 (M+H)+, found 137.0452.

  • 3
  • [ 4110-33-2 ]
  • [ 3939-09-1 ]
  • [ 34667-88-4 ]
  • 4
  • [ 4110-33-2 ]
  • [ 34667-88-4 ]
  • 5
  • [ 34667-88-4 ]
  • [ 100-61-8 ]
  • 2-(Methyl-phenyl-amino)-4-nitro-benzonitrile [ No CAS ]
  • 6
  • [ 350-32-3 ]
  • [ 34667-88-4 ]
YieldReaction ConditionsOperation in experiment
95% With Hexamethyldisiloxane; phosphorus pentoxide; In 1,2-dichloro-ethane; at 100℃; for 4.0h;Heating / reflux; A mixture of 2-fluoro-4-nitrobenzamide (0.83 g, 4.6 mmol) and phosphorus pentoxide/hexamethyl disiloxane in 1,2-dichloroethane (20 mL) was heated under nitrogen at 100° C. for 4 hours. Upon cooling, the solution was poured onto a plug of silica gel and washed with hexane (200 mL) followed by 5percent methanol/chloroform (400 mL). The methanol/chloroform washes were collected and concentrated under reduced pressure to give 2-fluoro-4-nitrobenzonitrile (0.71 g, 95percent) as a beige solid. 1H NMR (DMSO-d6): delta 8.46 (dd, J=9.5, 2.0 Hz, 1H), 8.37-8.22 (m, 2H).
86.73% With trichlorophosphate; In water; N,N-dimethyl-formamide; at 25℃; for 12.0h; To a solution of 15 5 (10g, 54.35mmol) in 63 DMF (100mL) was added 64 phosphorus oxychloride (35mL) dropwisely. And the mixture was stirred at 25°C for 12h. This mixture was treated with 65 ice water (300mL) for 30min. Then the mixture was extracted with EA, and the organic layer was washed with sat, dried with Na2SO4, filtered, and concentrated under reduced pressure to afford 66 product 6 (7.82g, 86.73percent) as a yellow solid. HRMS (ESI): m/z, calculated for C7H3FN2O2 167.0261 (M+H)+, found 167.0283.
  • 7
  • [ 34667-88-4 ]
  • [ 2365-48-2 ]
  • [ 35212-90-9 ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine; In acetonitrile; at 25℃; for 19.0h; Methyl 3-amino-6-nitrobenzothiophene-2-carboxylate: Methyl thioglycolate (0.08 mL, 0.85 mmol) was added to a solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (145 mg, 0.87 mmol), and triethylamine (0.14 mL, 1.0 mmol) in acetonitrile (20 mL) stirred under nitrogen at 25° C. After 3 hours further triethylamine (0.28 mL, 2.0 mmol) was added to the solution, which was stirred at 25° C. for a further 16 hours. The solvent was removed under reduced pressure to give a brown residue, which upon trituration with chloroform precipitated methyl 3-amino-6-nitrobenzothiophene-2-carboxylate (103 mg, 54percent) as a red brown solid, mp 228.5-229.5° C. 1H NMR (DMSO-d6): delta 8.87 (d, J=2.0 Hz, 1H), 8.32 (d, J=9.0 Hz, 1H), 8.15 (dd, J=8.8, 2.0 Hz, 1H), 7.26 (brs, 2H), 3.77 (s, 3H). Mass Spectrum (CI): 253 (100, MH+), 252 (52, M+).
  • 9
  • [ 34667-88-4 ]
  • [ 380241-60-1 ]
  • 10
  • [ 34667-88-4 ]
  • [ 380241-69-0 ]
  • 11
  • [ 34667-88-4 ]
  • [ 380241-81-6 ]
  • 12
  • [ 34667-88-4 ]
  • 6-fluoro-2-[2-(2-methoxy-ethoxymethoxy)-biphenyl-3-yl]-1<i>H</i>-indole-5-carboxamidine [ No CAS ]
  • 13
  • [ 34667-88-4 ]
  • 6-fluoro-<i>N</i>-hydroxy-2-[2-(2-methoxy-ethoxymethoxy)-biphenyl-3-yl]-1<i>H</i>-indole-5-carboxamidine [ No CAS ]
  • 14
  • [ 34667-88-4 ]
  • C27H26FN3O5 [ No CAS ]
  • 15
  • [ 34667-88-4 ]
  • {4-cyano-5-fluoro-2-[2-(2-methoxy-ethoxymethoxy)-biphenyl-3-ylethynyl]-phenyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 16
  • [ 34667-88-4 ]
  • 6-fluoro-2-(2-hydroxybiphenyl-3-yl)-1H-indole-5-carboxamidine hydrochloride [ No CAS ]
  • 20
  • [ 34667-88-4 ]
  • [ 198204-59-0 ]
  • 21
  • [ 584-48-5 ]
  • concentrated aqueous KOH-solution [ No CAS ]
  • [ 34667-88-4 ]
  • 22
  • [ 108-86-1 ]
  • radioactive bromine [ No CAS ]
  • [ 34667-88-4 ]
  • 23
  • [ 34667-88-4 ]
  • [ 86776-51-4 ]
  • 24
  • [ 34667-88-4 ]
  • [ 82380-18-5 ]
  • 25
  • [ 34667-88-4 ]
  • 4-Cyano-3-fluoro-benzenediazonium [ No CAS ]
  • 26
  • [ 34667-88-4 ]
  • 3-fluoro-4-cyanophenyl-4'-ethylbenzoate [ No CAS ]
  • 27
  • [ 34667-88-4 ]
  • 3-fluoro-4-cyanophenyl-4'-n-butylbenzoate [ No CAS ]
  • 28
  • [ 34667-88-4 ]
  • 3-fluoro-4-cyanophenyl-4'-n-pentylbenzoate [ No CAS ]
  • 29
  • [ 34667-88-4 ]
  • 3-fluoro-4-cyanophenyl-4'-n-hexylbenzoate [ No CAS ]
  • 30
  • [ 34667-88-4 ]
  • 3-fluoro-4-cyanophenyl-4'-n-heptylbenzoate [ No CAS ]
  • 31
  • [ 34667-88-4 ]
  • [ 100-53-8 ]
  • 2-(benzylsulfanyl)-4-nitrobenzonitrile [ No CAS ]
  • 32
  • [ 34667-88-4 ]
  • [ 900174-91-6 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In methanol; under 2844.39 Torr; for 22.0h; [00293] A solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (0.541 g, 2.43 mmol) in methanol (20 mL) and 6N hydrochloric acid (3 mL) was hydrogenated (55 psi) over 10percent palladium on carbon (164 mg) for 22 li. The reaction mixture was filtered and concentrated in vacuo to afford 77A (0.65 g, 100percent). 1H NMR (400 MHz, CD3OD) delta 4.23 (s, 2 H), 7.29 (d, J=8.79 Hz, 2 H), 7.68 (t, J=I.91 Hz, 1 H).
  • 33
  • [ 15231-91-1 ]
  • [ 34667-88-4 ]
  • [ 526218-63-3 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; In methanol; acetonitrile; Production Example 6-1 2-(6-bromo-2-naphthyloxy)-4-nitrobenzonitrile After heating to reflux <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (1 g), 6-bromo-2-naphthol (1.41 g), potassium fluoride/alumina (0.7 g) and 18-crown-6 (0.16 g) in acetonitrile, the mixture was reacted for 12 hours. It was then cooled to room temperature, the insoluble portion was filtered using celite, the ethyl acetate layer was washed with water and saturated saline and then dried over magnesium sulfate, and the solvent was distilled off. Methanol was added to the residue for crystallization to obtain 1.43 g of 2-(6-bromo-2-naphthyloxy)-4-nitrobenzonitrile. 1H-NMR (CDCl3) delta:7.31 (1H, dd, J=2.4, 8.8 Hz), 7.54 (1H, d, J=2.0 Hz), 7.62-7.70 (3H, m), 7.88 (1H, s), 7.90 (1H, s), 8.01 (1H, dd, J=2.0, 8.4 Hz), 8.08 (1H, s).
  • 34
  • [ 110-91-8 ]
  • [ 34667-88-4 ]
  • [ 915390-02-2 ]
  • 35
  • [ 34667-88-4 ]
  • [ 1027259-01-3 ]
YieldReaction ConditionsOperation in experiment
39% With hydrazine hydrate; In ethanol; at 80℃; for 12.0h; To a solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong>, 273 (5 g, 30.1 mmols) in ethanol (50 ml) was added hydrazine hydrate (15 ml). The resulting solution was heated at 80 C for 12 h. The reaction mixture was poured into water. The solid formed, consistent with the title compound was filtered and dried. Yield 2.1 g (39 %). 1 H NMR (400 MHz, DMSO) d 8.13 (d, J = 1.9 Hz, 1H), 7.91 (d, J = 8.8 Hz, 1H), 7.72 (dd, J = 8.8, 2.0 Hz, 1H).
With hydrazine; In water; isopropyl alcohol; at 80℃; for 12.0h; Example 69; Synthesis of 2-(pyridin-2-ylamino)-lH-benzimidazole-5-carboxylic acid (3 -amino- IH- indazol-6-yl)-amideTo a solution of <strong>[34667-88-4]2-fluoro-4-nitrobenzonitrile</strong> (10 mmol) in isopropanol (30 mL) was added aqueous hydrazine (4 mL). The resulting solution was heated at 800C for 12 h. The reaction mixture was then concentrated, water (30 mL) was added, and the solution was extracted with ethyl acetate (2x25 mL). The combined organics were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate. The volatiles were removed in vacuo yielding 3-amino-6-nitroindazole as an orange solid, which was utilized for further transformation without further purification.The nitro compound from above was hydrogenated, following general procedure F, to yield 3,6-diaminoindazole.2-Isothiocyanatopyridine (4 mmol), prepared from 2-aminopyridine employing general procedure A, was reacted with methyl 3,4-diaminobenzoate as described in general procedure B to afford 2-(pyridin-2-ylamino)-lH-benzirnidazole-S-carboxylic acid methyl ester. This ester was hydrolyzed, following general procedure C, to obtain 2-(pyridin-2- ylamino)-lH-benzimidazole-5-carboxylic acid.The cafboxylic acid (0.5 mmol) from above was coupled with aforementioned 3,6- diaminoindazole (0.5 mmol) using HBTU as described in general procedure D to afford 2- <n="60"/>(pyridin-2-ylamino)-lH-benzimidazole-5-carboxylic acid (3-amino-lH-indazol-6-yl)-amide. MS: m/z 385 (M+H)+.
 

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Chemical Structure| 172921-32-3

A201513 [172921-32-3]

2,5-Difluoro-4-nitrobenzonitrile

Similarity: 0.94

Chemical Structure| 143306-27-8

A176266 [143306-27-8]

2-Fluoro-6-nitrobenzonitrile

Similarity: 0.94

Chemical Structure| 1247885-40-0

A346412 [1247885-40-0]

2,3-Difluoro-5-nitrobenzonitrile

Similarity: 0.92

Chemical Structure| 1214328-20-7

A116602 [1214328-20-7]

2-Fluoro-3-nitrobenzonitrile

Similarity: 0.91

Chemical Structure| 80517-21-1

A230218 [80517-21-1]

4-Fluoro-2-nitrobenzonitrile

Similarity: 0.90

Nitriles

Chemical Structure| 172921-32-3

A201513 [172921-32-3]

2,5-Difluoro-4-nitrobenzonitrile

Similarity: 0.94

Chemical Structure| 143306-27-8

A176266 [143306-27-8]

2-Fluoro-6-nitrobenzonitrile

Similarity: 0.94

Chemical Structure| 1247885-40-0

A346412 [1247885-40-0]

2,3-Difluoro-5-nitrobenzonitrile

Similarity: 0.92

Chemical Structure| 1214328-20-7

A116602 [1214328-20-7]

2-Fluoro-3-nitrobenzonitrile

Similarity: 0.91

Chemical Structure| 80517-21-1

A230218 [80517-21-1]

4-Fluoro-2-nitrobenzonitrile

Similarity: 0.90