Home Cart Sign in  
Chemical Structure| 64188-97-2 Chemical Structure| 64188-97-2

Structure of 64188-97-2

Chemical Structure| 64188-97-2

*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 [ 64188-97-2 ]

CAS No. :64188-97-2
Formula : C6H7N3O
M.W : 137.14
SMILES Code : O=C(N)C1=CC=NC=C1N
MDL No. :MFCD08235178
InChI Key :MRZUGOPPUMNHGA-UHFFFAOYSA-N
Pubchem ID :10749239

Safety of [ 64188-97-2 ]

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

Computational Chemistry of [ 64188-97-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 36.74
TPSA ?

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

82.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.54
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

-0.4
Log Po/w (WLOGP)?

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

-0.23
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.

-1.01
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

-0.21
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.26

Water Solubility

Log S (ESOL):?

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

-0.82
Solubility 20.9 mg/ml ; 0.153 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.

-0.86
Solubility 19.0 mg/ml ; 0.139 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

-1.23
Solubility 8.15 mg/ml ; 0.0594 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.

-7.42 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)

1.23

Application In Synthesis of [ 64188-97-2 ]

* 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 [ 64188-97-2 ]

[ 64188-97-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 7579-20-6 ]
  • [ 64188-97-2 ]
YieldReaction ConditionsOperation in experiment
87% With ammonium chloride; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 40℃; for 72h;Inert atmosphere; Ammonium hydrochloride (4.98 g, 93.2 mmol) was added to 3-aminoisonicotinic acid (9.90g, 71.7 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (35.4 g, 93.2 mmol) and N-ethyl-N-isopropylpropan-2-amine (37.5mL, 215.02 mmol) in DMF (100 mL) under nitrogen. The resulting solution was stirred at 40 °C for 72 hours. The mixture was evaporated to provide the crude material. The crude product was purified by flash silica chromatography with elution gradient 5percent MeOH in DCM. Pure fractions were evaporated to dryness to afford 3-aminoisonicotinamide (8.57 g, 87 percent) as a yellow gum.
77% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; N,N-dimethyl-formamide; at 20℃; To the suspension of isonicotinic acid (1.00 g, 7.24 mmol) in DMF (10 mL) were added HOBt (978 mg, 7.24 mmol), 7 M ammonia solution in methanol (2.06 mL, 14.5 mmol) and EDC*HCl (2.08 g, 10.9 mmol). The mixture was stirred overnight at room temperature. Solvent was distilled off in vacuo, and CH2Cl2 and saturated NaHCO3 aqueous solution were added to the residue. Organic phase was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (5-->8percent MeOH-CH2Cl2) to obtain the title compound (767 mg, 5.60 mmol, 77percent) as a pale yellow powder. 1H NMR (DMSO-d6) delta: 6.59 (2H, br s), 7.39 (1H, d, J = 5.3 Hz), 7.43 (1H, br s), 7.72 (1H, d, J = 5.3 Hz), 8.00 (1H, br s), 8.12 (1H, s). ESI-MS m/z: 138 (M+H)+.
General method for synthesis of 4-chloropyrido[3,4-d]pyrimidine: The mixture of 3-aminoisonicotinic acid (B-1) (7 g, 50 mmol) and DMF (0.2 mL) in thionyl chloride (100 mL) is stirred at reflux for 2 h. The mixture is then concentrated in vacuo. The residue is dissolved in THF (30 mL) and the resulting solution (solution A) is used directly in the next step. [00676] To a stirred mixture of ammonium hydroxide (100 mL), the above solution A (30 mL) is added dropwise while the reaction temperature is maintained between 25 °C to 30 °C using an ice-water bath. The resulting mixture is stirred at RT for 2 h and then water (100 mL) is added. The organic layer is separated, washed with water (100 mL x 2), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo to afford the amide (B-2).
With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃; for 15h; General procedure: The syntheses of compounds 3a-3x were mainly referred to literature method [35]. A mixture of 1a-1q, 1w, 1x (2mmol), EDC?HCl (575mg, 3mmol), HOBt (446mg, 3.3mmol), NH4Cl (348mg, 6.5mmol) and DIPEA (2.3mL, 13mmol) in DMSO (7mL) was stirred at room temperature for 15h. The mixture was extracted with EtOAc three times, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 3a-3q, 3w, 3x. A mixture of 2r-2v (2mmol) and NH3·H2O (25?28wtpercent, 80mmol) in sealed tube was heated at 100°C for 12h. The mixture was cooled to room temperature and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 3r-3v.
Example 2.10; 2-(1-Benzofuran-2-yl)pyrido[3,4-d]pyrimidin-4(3H)-one (C: R=7-aza, R'~1-benzofuran-2-yl); A slurry of 3-aminoisonicotinic acid (1.556 g, 11.3 mmol) and CDI (2.82 g, 17.4 mmol) in dmf (20 mL) was heated to 40°C for 0.5 h then cooled. Concentrated aqueous ammonia (50 mL) was added and the mixture was stirred for 15 min then extracted with ethyl acetate. Removal of the solvent gave a solid which was dissolved in pyridine (20 mL), 1-benzofuran-2-carbonyl chloride (from benzo[ib]furan-2-carboxylic acid; 2.006 g, 12.4 mmol) was added and the mixture was refluxed for 0.5 h, poured onto ice and filtered to give theintermediate amide (E: R=4-aza, R'=1-benzofuran-2-yl). The intermediate amide was refluxed in 5percent aqueous KOH (20 mL)/EtOH (10 ml_) for 0.5 h to give the product (0.303 g, 10percent) as a solid. 1H NMR (DMSO-d6) 5 ppm 13.07 (bs, 1H), 9.15 (d, 1H, J=0.8 Hz), 8.68 (d, 1H, J=5.1 Hz), 8.11 (d, 1H, J=0.8 Hz), 7.98 (dd, 1H, J=5.1, 0.8 Hz), 7.84 (dd, 1H, J=7.5, 0.8 Hz), 7.77 (dd, 1H, J=8.3, 0.8 Hz), 7.51 (ddd, 1H, J=8.3, 7.3, 1.2 Hz), 7.38 (td, 1H, J=7.5, 0.8 Hz). ACPI-MS Found: [M+H]+= 264.

  • 2
  • [ 64188-97-2 ]
  • [ 908240-50-6 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 64188-97-2 ]

Amides

Chemical Structure| 1453-82-3

A154365 [1453-82-3]

Isonicotinamide

Similarity: 0.87

Chemical Structure| 251101-36-7

A583278 [251101-36-7]

3-Methylisonicotinamide

Similarity: 0.79

Chemical Structure| 60524-14-3

A133913 [60524-14-3]

5-Amino-3-pyridinecarboxamide

Similarity: 0.79

Chemical Structure| 342899-34-7

A489661 [342899-34-7]

3-Amino-2-chloroisonicotinamide

Similarity: 0.78

Chemical Structure| 58539-65-4

A129050 [58539-65-4]

2-Methylnicotinamide

Similarity: 0.75

Amines

Chemical Structure| 1453-82-3

A154365 [1453-82-3]

Isonicotinamide

Similarity: 0.87

Chemical Structure| 251101-36-7

A583278 [251101-36-7]

3-Methylisonicotinamide

Similarity: 0.79

Chemical Structure| 60524-14-3

A133913 [60524-14-3]

5-Amino-3-pyridinecarboxamide

Similarity: 0.79

Chemical Structure| 342899-34-7

A489661 [342899-34-7]

3-Amino-2-chloroisonicotinamide

Similarity: 0.78

Chemical Structure| 58539-65-4

A129050 [58539-65-4]

2-Methylnicotinamide

Similarity: 0.75

Related Parent Nucleus of
[ 64188-97-2 ]

Pyridines

Chemical Structure| 1453-82-3

A154365 [1453-82-3]

Isonicotinamide

Similarity: 0.87

Chemical Structure| 251101-36-7

A583278 [251101-36-7]

3-Methylisonicotinamide

Similarity: 0.79

Chemical Structure| 60524-14-3

A133913 [60524-14-3]

5-Amino-3-pyridinecarboxamide

Similarity: 0.79

Chemical Structure| 342899-34-7

A489661 [342899-34-7]

3-Amino-2-chloroisonicotinamide

Similarity: 0.78

Chemical Structure| 58539-65-4

A129050 [58539-65-4]

2-Methylnicotinamide

Similarity: 0.75