206201-64-1|6-Formylnicotinonitrile| Ambeed

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Quality Control of [ 206201-64-1 ] Purity: 97% SDS Specification

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Product Details of [ 206201-64-1 ]

CAS No. :	206201-64-1
Formula :	C₇H₄N₂O
M.W :	132.12
SMILES Code :	O=CC1=CC=C(C=N1)C#N
MDL No. :	MFCD13189079
InChI Key :	DMDMMMFMXWZSLM-UHFFFAOYSA-N
Pubchem ID :	21364144

Safety of [ 206201-64-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 206201-64-1 ] 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	3.0
Num. H-bond donors	0.0
Molar Refractivity	34.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	53.75 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.62
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	0.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.77
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.	-0.84
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	1.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.47

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.27
Solubility	7.09 mg/ml ; 0.0537 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.	-1.06
Solubility	11.4 mg/ml ; 0.0863 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	-2.02
Solubility	1.25 mg/ml ; 0.00946 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.	-6.84 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	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)	1.37

Application In Synthesis of [ 206201-64-1 ]

* 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 [ 206201-64-1 ]

[ 206201-64-1 ] Synthesis Path-Downstream 1~35

1
[ 206201-64-1 ]
[ 105-56-6 ]
[ 668997-90-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With piperidine; In ethanol; at 20℃; for 3h;	The compound of Example 33A (421 mg, 3.2 mmol), ethyl cyanoacetate (360 mg, 3.2 mmol) and piperidine (8.1 mg, 0.095 mmol) are dissolved in absolute ethanol (7.5 ml) and stirred at room temperature for 3 hours. During this time a precipitate is formed, which is filtered and washed with a minimal amount of additional ethanol (1 ml). Yield: 395 mg (50percentof th.) HPLC (method 8) = 4.18 min MS (ESIpos) :m/z = 228(M+H) +lH-NMR (400 MHz, DMSO-d6):6 = 9.21 (d, 1H); 8.54 (dd, 1H) ; 8.46 (s, 1H); 8.12 (d, 1H) ; 4.35 (q, 2H); 1.32 (t, 3H) ppm.

References: [1]Patent: WO2004/20412,2004,A1 .Location in patent: Page 40.

2
[ 31795-61-6 ]
[ 206201-64-1 ]

Yield	Reaction Conditions	Operation in experiment
48%		Oxalyl chloride (936 mg, 7.38 mmol) is dissolved in dichlormethane (8 ml) under an argon atmosphere and cooled to-78 C in an acetone dry-ice bath. Dimethylsulfoxide (1. 153 g, 14. 76 mmol) is added dropwise and the mixture is stirred for 20 minutes at - 78 C. The compound of Example 32A (900 mg, 6.71 mmol) is added dropwise as a dichloromethane (7 ml) solution. The reaction is stirred for an additional two hours at - 78 C. Triethylamine (3.05 g, 30.19 mmol) is added and the reaction is kept at-78 C for 10 minutes, then allowed to warm to room temperature. The reaction is quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate phase is washed with bicarbonate and brine, dried over magnesium <Desc/Clms Page number 48>sulphate monohydrate, filtered and concentrated to afford a yellow oil. The crude oil is purified by column chromatography on silica gel with dichloromethane as eluent. Yield: 424 mg (48percent of th.) HPLC (method 8): Rt1. 19 min MS(EI) :m/z= 132 (M) +IH-NMR (200 MHz,DMSO-d6) :6 = 5.69 (t, 1H); 7.65 (d, 1H); 8.31 (dd, 1H); 8.93 (d, 1H) ppm.

References: [1]Patent: WO2004/20412,2004,A1 .Location in patent: Page 47; 48.

3
[ 3222-48-8 ]
[ 206201-64-1 ]

Yield	Reaction Conditions	Operation in experiment
50%		Preparation 18 6-FormylnicotinonitrileA mixture of 6-methylnicotinonitrile (10.0 g, 84.6 mmol) and iodine (20.0 g, 78.8 mmol) in dimethylsulfoxide (150 mL) was heated at 15O0C under nitrogen for 20 minutes (reaction exhaust was scrubbed with bleach to remove dimethyl sulfide). After cooling to room temperature saturated aqueous sodium bicarbonate (200 mL) was added carefully and the resulting mixture was extracted with toluene (3 x 100 mL). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to give the desired product as an orange oil (5.65 g, 50percent) which was used without further purification. 1H NMR (CDCI3, 400 MHz) delta 8.06 (1H, d), 8.17 (1H, dd), 9.05 (1H, d), 10.12 (1H, s).
	With selenium(IV) oxide; In 1,4-dioxane; water;	EXAMPLE 51A 6-formylnicotinonitrile A solution of 6-methylnicotinonitrile (590 mg, 5.0 mmol) in dioxane (10 mL) and water (0.5 mL) was treated with selenium dioxide (555 mg, 5.0 mmol), heated to reflux for 16 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel with hexanes then 9:1/hexanes:ethyl acetate to provide the desired product. 1H NMR (300 MHz, CDCl3) delta 10.13-10.12 (m, 1H), 9.06-9.05 (m, 1H), 8.19-8.16 (m, 1H), 8.09-8.05 (m, 1H).
	With iodine; dimethyl sulfoxide; at 150℃; for 0.333333h;Inert atmosphere;	6-Formylnicotinonitrilemi xture of 5-cyano-2-methylpyridine (750 mg, 6.3 mmol) and iodine (1.5 g, 5.7mmol) in DMSO (10 mL) was heated to 150°C under nitrogen for 20 mm. The reactionmixture was cooled to room temperature and quenched with 10percent aqueous NaHCO3 solution. The organic product was extracted with EtOAc. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to get crude 6-formylnicotinonitrile (400 mg), which was carried through without furtherpurification.

References: [1]Chemical Science,2016,vol. 7,p. 346 - 357.
[2]Patent: WO2007/96763,2007,A2 .Location in patent: Page/Page column 60.
[3]Patent: US2002/19527,2002,A1 .
[4]Patent: WO2013/6408,2013,A1 .Location in patent: Page/Page column 43.
[5]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 559 - 576.

4
4-((((1-methyl-1H-imidazol-5-yl)methyl)amino)methyl)-2-(1-naphthyl)benzonitrile dihydrochloride [ No CAS ]
[ 206201-64-1 ]
6-(((4-cyano-3-(1-naphthyl)benzyl)((1-methyl-1H-imidazol-5-yl)methyl)amino)-methyl)nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride;silica gel; In 1,2-dimethoxyethane; acetic acid; ethyl acetate;	EXAMPLE 288 6-(((4-cyano-3-(1-naphthyl)benzyl)((1-methyl-1H-imidazol-5-yl)methyl)amino)methyl)nicotinonitrile A solution of Example 192D (35 mg, 0.10 mmol) in 5percent acetic acid/DME (1.0 mL) at room temperature was treated with <strong>[206201-64-1]6-formylnicotinonitrile</strong> (30 mg, 3.0 mmol) and 4A molecular sieves, stirred for 1 hour, treated with sodium triacetoxyborohydride (40 mg, 2.0 mmol), stirred for 16 hours, treated with ethyl acetate (1.0 mL), washed with saturated sodium bicarbonate and brine, filtered through a Chem Elut.(R). CE1000M tube (Alltech, Northbrook, Ill.), and concentrated. The concentrate was purified by preparative HPLC (CH3CN/0.010M NH4OAc) to provide the desired product. MS (APCI(+)) m/z 469 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 9.78 (s, 1H), 8.88 (s, 1H), 8.17 (dd, 1H), 8.07 (d, 1H), 8.05 (d, 1H), 7.93 (d, 1H), 7.66-7.45 (m, 8H), 7.39 (d, 1H), 3.83 (s, 2H), 3.80 (s, 2H), 3.69 (s, 2H), 3.50 (s, 3H).

References: [1]Patent: US2002/19527,2002,A1 .

6
[ 206201-64-1 ]
[ 1097206-19-3 ]
[ 1097207-04-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 18h;	Scheme 55 To Example 2 (0.1 g, 0.3 mmol) in DCE (1.1 ml_) was added the aldehyde from Scheme 9 (0.05 g, 0.3 mmol) and Na(OAc)3BH (0.09 g, 0.4 mmol). The reaction was stirred for 18 h at room temperature. DCM was added and the mixture was washed with saturated NaHCO3, water, and brine. The residue was purified by silica gel chromatography (0-90percent EtOAc/Hex over 30 minutes) to provide Example 81 (0.96 g, 0.19 mmol).

References: [1]Patent: WO2009/5646,2009,A2 .Location in patent: Page/Page column 244.

7
[ 16173-99-2 ]
[ 206201-64-1 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2 A DCM solution (160 ml_) of containing the aldehyde from step 1 (4.1 g, 31 mmol) was cooled to -78 0C. Ozone was bubbled through the reaction mixture until the solution turned light blue (-30 minutes). The reaction was then purged with oxygen and then dimethylsulfide (7 ml_, 95 mmol) was added. The reaction was stirred for 18 h after taking the cold bath away. Washed the mixture with water and brine. Dried (MgSO4) the organic layer, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-20percent EtOAc/Hex) to provide the aldehyde (1.3 g, 9.7 mmol).

References: [1]Patent: WO2009/5646,2009,A2 .Location in patent: Page/Page column 147.

8
[ 206201-64-1 ]
[ 292638-85-8 ]
[ 5619-07-8 ]
dimethyl 2-benzyl-5-(5-cyanopyridin-2-yl)pyrrolidine-2,4-dicarboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 8271 - 8274.

9
[ 50-00-0 ]
[ 206201-64-1 ]
[ 109-73-9 ]
2-butyl-6-cyanoimidazo[1,5-a]pyridinium chloride [ No CAS ]

References: [1]Organic Letters,2011,vol. 13,p. 5256 - 5259.
[2]Organic Letters,2012,vol. 14,p. 3162 - 3165.

10
[ 206201-64-1 ]
2-butyl-6-cyanoimidazo[1,5-a]pyridinium tetraphenylborate [ No CAS ]

References: [1]Organic Letters,2011,vol. 13,p. 5256 - 5259.
[2]Organic Letters,2012,vol. 14,p. 3162 - 3165.

11
[ 206201-64-1 ]
[ 1097211-72-7 ]
[ 1427712-21-7 ]

Yield	Reaction Conditions	Operation in experiment
0.07 g	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 16h;	To Example 806 (0.06 g, 0.18 mmol) in DCE (1 mL) was added <strong>[206201-64-1]2-formyl-5-cyanopyridine</strong> (0.03 g, 0.23 mmol) [prepared in Scheme 106] and sodium triacetoxyborohydride (0.06 g, 0.28 mmol). The reaction was stirred at room temperature for 16 h and then diluted with DCM. The mixture was washed with saturated NaHCO3, water, and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-60percent EtOAc/hex over 30 minutes) to provide Example 883 (0.07 g, 0.16 mmol).

References: [1]Patent: US2013/72468,2013,A1 .Location in patent: Paragraph 1185; 1186.

12
[ 206201-64-1 ]
[ 292638-85-8 ]
[ 5619-07-8 ]
(2R,4S,5R)-dimethyl 2-benzyl-5-(5-cyanopyridin-2-yl)pyrrolidine-2,4-dicarboxylate [ No CAS ]
(2S,4R,5S)-dimethyl 2-benzyl-5-(5-cyanopyridin-2-yl)pyrrolidine-2,4-dicarboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 9471 - 9476.

13
[ 206201-64-1 ]
[ 122734-32-1 ]
tert-butyl (2-(((5-cyanopyridin-2-yl)methyl)(methyl)amino)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 0 - 20℃; for 2h;	tert-Butyl (2-(((5-cyanopyridin-2-yI)methyl)(methyl)ami no)ethyl)carbamateso lution of tert-butyl (2-(methylamino)ethyl)carbamate (150 mg, 0.86 mmol) in1,2-dichloroethane (5 mL)was added to a solution of <strong>[206201-64-1]6-formylnicotinonitrile</strong> (120 mg, 0.86 mmol) in 1,2-dichloroethane (5 mL), followed by sodium triacetoxyborohydride (0.36 mL,2.58 mmol) at 0°C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. The reaction mixture was then quenched with 10percent aqueous NaHCO3solution and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crudeproduct was purified by flash column chromatography (neutral alumina, eluent 5percent MeOHin CH2CI2) to afford tert-butyl (2-(((5-cyanopyridin-2-yl)methyl)(methyl)amino)ethyl)carbamate (200 mg, yield 23percent) as a brown liquid. MS (ESI) m/z: Calculated for C15H22N402: 290.17; found: 291.2 (M+H).

References: [1]Patent: WO2013/6408,2013,A1 .Location in patent: Page/Page column 43; 44.

14
[ 206201-64-1 ]
[ 600-18-0 ]
(R)-6-(4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-yl)nicotinonitrile [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14532 - 14539.

15
[ 206201-64-1 ]
[ 600-18-0 ]
6-(4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-yl)nicotinonitrile [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14532 - 14539.

16
[ 206201-64-1 ]
5-(4-amidinophenyl)-3-(5-amidinopyridin-2-yl)isoxazole dihydrochloride [ No CAS ]