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Quality Control of [ 769-92-6 ] Purity: 98% SDS Specification

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Product Details of [ 769-92-6 ]

CAS No. :	769-92-6
Formula :	C₁₀H₁₅N
M.W :	149.23
SMILES Code :	NC1=CC=C(C(C)(C)C)C=C1
MDL No. :	MFCD00007899
InChI Key :	WRDWWAVNELMWAM-UHFFFAOYSA-N
Pubchem ID :	69861

Safety of [ 769-92-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Computational Chemistry of [ 769-92-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	50.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.02
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.57
Log P_o/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.	2.76
Log P_o/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	2.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.8
Solubility	0.234 mg/ml ; 0.00157 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.	-2.9
Solubility	0.188 mg/ml ; 0.00126 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	-3.23
Solubility	0.0881 mg/ml ; 0.00059 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.	-5.29 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	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)	1.0

Application In Synthesis of [ 769-92-6 ]

* 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 [ 769-92-6 ]

[ 769-92-6 ] Synthesis Path-Downstream 1~26

1
[ 253185-03-4 ]
[ 769-92-6 ]
[ 1625-91-8 ]
[ 53692-25-4 ]
[ 76783-54-5 ]

References: [1]Liebigs Annalen der Chemie,1980,p. 2012 - 2020.
[2]Liebigs Annalen der Chemie,1980,p. 2012 - 2020.

2
[ 253185-03-4 ]
[ 5369-19-7 ]
[ 769-92-6 ]
[ 6310-21-0 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 4479 - 4482.
[2]Journal of Organic Chemistry,1984,vol. 49,p. 4479 - 4482.

3
[ 769-92-6 ]
[ 253185-03-4 ]
[ 23132-52-7 ]
[ 3282-56-2 ]
[ 1625-91-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1995,vol. 114,p. 311 - 316.

4
[ 769-92-6 ]
[ 4385-76-6 ]
N-(4-tert-butyl-phenyl)-4-pyridin-4-yl-benzamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 631 - 634.

5
[ 769-92-6 ]
[ 68176-57-8 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.

6
[ 214045-86-0 ]
[ 769-92-6 ]
[ 848841-45-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	In 1,4-dioxane; water; butan-1-ol; at 80℃;	1 B) (4-TERT-BUTVL-PHENVL)-(6-FLUORO-ISOQUINOLIN-1-VL)-AMINE 1-CHLORO-6-FLUORO-ISOQUINOLINE (1 g, 6.13 MMOL) is dissolved in n-BuOH (20 mL) and 4-T-BUTYL-ANILINE (1. 1 g, 6.74 MMOL). 4 N HCI (1 mL) in dioxane (1 mL) is added dropwise. The resulting mixture is heated at 80C overnight. The mixture is rotary evaporated, and the residues dissolved in ethyl acetate, washed with saturated NAHC03, brine and dried over MGS04. The solute is removed and after CONCENTRATION IN VACUO, the organic layer is further purified by silica gel column (hexane 90% to 10% ethyl acetate/hexane) to afford a yellow solid (900 mg, 56%). M+H+ = 295.3. 'H NMR (300 MHz) (DMSO); 8 1.29 (s, 9H), 7.13 (d, 1H, J=6 Hz), 7.34 (d, 2H, J=8.67 Hz), 7.50 (m, 1H), 7.60 (dd, 1H, J=2.64, 9. 8 HZ) =7. 72 (d, 2H, 8.67 HZ), 7. 96 (d, 1H, 5.65 Hz), 8. 61 (dd, 1H, J=5.46, 9.23 Hz), 9.16 (s, 1H).; 21 B) (4-TERT-BUTVL-PHENVL)-(6-FLUORO-ISOQUINOLIN-1-VL)-AMINE A solution of <strong>[214045-86-0]1-chloro-6-fluoro-isoquinoline</strong> (1 g, 6.13 MMOL) and 4-tert-butyl- aniline (1. 1 g, 6.74 MMOL) in nBuOH (20 mL) and 4N HCI/DIOXANE (1 mL) is heated at 80C overnight. The mixture is concentrated and the residue is made basic with sat. NaHC03 and extracted with EtOAc. The organic layer is dried, concentrated and purified by silica gel column (Hexane to 10% ETOAC/HEXANE) to afford yellow solid (900 mg, 56%). M+H+=295. 3. H NMR (400 MHz, DMSO-D6) 5 1.29 (s, 9H), 7.13 (d, 1H, J= 6 Hz), 7.34 (d, 2H, J= 8.67 Hz), 7.50 (m, 1 H), 7.60 (dd, 1 H, J = 2.64, 9.8 Hz) 7.72 (d, 2H, J = 8.67 Hz), 7.96 (d, 1 H, J= 5.65 Hz), 8.61 (dd, 1H J=5.46, 9.23Hz), 9.16 (s, 1H).

References: [1]Patent: WO2005/28444,2005,A1 .Location in patent: Page/Page column 48; 70.

7
[ 80041-89-0 ]
[ 769-92-6 ]
[ 1019532-61-6 ]

References: [1]Synlett,2010,p. 2101 - 2105.

8
[ 618-89-3 ]
[ 769-92-6 ]
[ 1284180-29-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 120℃;Inert atmosphere;	To a solution of bromide (or triflate) (1 equiv) in toluene (0.1 M) was added aniline (1.2 equiv), Cs2CO3 (1.4 equiv) BINAP (0.08 equiv), and Pd(OAc)2 (0.05 equiv) at room temperature. The reaction mixture was allowed to stir at 120 C for 4-48 h. Once the reaction appeared to be complete by consumption of the bromide (or triflate) by TLC analysis, the mixture was allowed to cool to room temperature, diluted with EtOAc, washed with 2M aq HCl (2x), brine, and dried over sodium sulfate. The solution was concentrated, loaded on silica gel, and purified by silica gel chromatography.

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1464 - 1468.

9
[ 500-22-1 ]
[ 119072-55-8 ]
[ 769-92-6 ]
[ 1072-84-0 ]
[ 1417699-82-1 ]