[ CAS No. 97483-79-9 ]

Name: 97483-79-9|Ethyl 6-cyanopicolinate|95%
Brand: Ambeed
SKU: A444383
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Quality Control of [ 97483-79-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 97483-79-9 ]

Product Details of [ 97483-79-9 ]

CAS No. :	97483-79-9	MDL No. :	MFCD09261080
Formula :	C₉H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FYOOHRDXEPERKP-UHFFFAOYSA-N
M.W :	176.17 g/mol	Pubchem ID :	13415158
Synonyms :

Calculated chemistry of [ 97483-79-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.04
TPSA :	62.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	1.46
Log Po/w (WLOGP) :	1.13
Log Po/w (MLOGP) :	0.04
Log Po/w (SILICOS-IT) :	1.51
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.0
Solubility :	1.78 mg/ml ; 0.0101 mol/l
Class :	Very soluble
Log S (Ali) :	-2.39
Solubility :	0.72 mg/ml ; 0.00408 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.59
Solubility :	0.454 mg/ml ; 0.00258 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Safety of [ 97483-79-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 97483-79-9 ]

* 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.

Upstream synthesis route of [ 97483-79-9 ]
Downstream synthetic route of [ 97483-79-9 ]

[ 97483-79-9 ] Synthesis Path-Upstream 1~5

1
[ 617-35-6 ]
[ 100-70-9 ]
[ 58481-14-4 ]
[ 97483-79-9 ]

Reference： [1] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
[2] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744

2
[ 21190-88-5 ]
[ 97483-79-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	for 16 h; Inert atmosphere; Reflux	CuCN (31,1g, 348mmol) was added into ethyl 6-bromopicolinate (16 g, 69.5mmol) in 608ml pyridine. The mixture was refluxed under argon for 16h, filtered through celite, and concentrated in vacuo. Saturated NaHCO₃ solution was added followed by extracted with DCM for three times. The mixture was purified with flash chromatography in hexane/EE=1:1. TLC [hexane/EE 1:1]: R_f = 0.65 Yield: 7.3 g,(60percent). ¹HNMR (600 MHz, CDCl₃): δ= 8.32(dd, 1H, J=1.15, 7.97Hz), 8.04(t, 1H,J=7.86, 7.86Hz), 7.88 (dd, 1H, J=1.13, 7.76Hz), 4.52(q, 2H, J=7.13, 7.13,7.12Hz), 1.40(t, 3H, J=7.13, 7.13Hz). ¹³C NMR (300 MHz, CDCl₃): δ= 163.76,150.06, 138.70, 134,23, 131.40, 128.12, 116.62, 62.89, 14.44 HRMS: 177.0669[M +H], calculated 177.0664[M + H] +.
60%	for 16 h; Inert atmosphere; Reflux	CuCN (31,1g, 348mmol) was added into ethyl 6-bromopicolinate (16 g, 69.5mmol) in 608 ml pyridine. The mixture was refluxed under argon for 16h, filtered through celite, and concentrated in vacuo. Saturated NaHCO₃ solution was added followed by extracted with DCM for three times. The mixture was purified with flash chromatography in hexane/EE=1:1. TLC [hexane/EE 1:1]: R_f = 0.65 Yield: 7.3 g,(60percent). ¹HNMR (600 MHz, CDCl₃): δ= 8.32(dd, 1H, J=1.15, 7.97Hz), 8.04(t, 1H,J=7.86, 7.86Hz), 7.88 (dd, 1H, J=1.13, 7.76Hz), 4.52(q, 2H, J=7.13, 7.13,7.12Hz), 1.40(t, 3H, J=7.13, 7.13Hz). ¹³C NMR (300 MHz, CDCl₃): δ= 163.76,150.06, 138.70, 134,23, 131.40, 128.12, 116.62, 62.89, 14.44 HRMS: 177.0669[M +H], calculated 177.0664[M + H] +.

Reference： [1] Patent: EP2690102, 2014, A1, . Location in patent: Paragraph 0070; 0073
[2] Patent: WO2014/15993, 2014, A1, . Location in patent: Page/Page column 35

3
[ 21190-88-5 ]
[ 97483-79-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3922 - 3935

4
[ 30062-31-8 ]
[ 7677-24-9 ]
[ 97483-79-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 2, p. 565 - 571

5
[ 617-35-6 ]
[ 100-70-9 ]
[ 58481-14-4 ]
[ 97483-79-9 ]

Reference： [1] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
[2] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744

[ 97483-79-9 ] Synthesis Path-Downstream 1~44

1
[ 617-35-6 ]
[ 100-70-9 ]
[ 58481-14-4 ]
[ 97483-79-9 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 731 - 744
[2]Heterocycles,1987,vol. 26,p. 731 - 744

2
[ 30062-31-8 ]
[ 7677-24-9 ]
[ 97483-79-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 565 - 571

3
[ 97483-79-9 ]
1-{3-[2-(3,4-dimethoxyphenoxy)ethyl]-2-oxo-3,9-diazabicyclo[3.3.1]nonan-9-yl}-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

4
[ 97483-79-9 ]
9-(3,5-dichlorophenylsulfonyl)-3-[2-(3,4-dimethoxyphenoxy)ethyl]-3,9-diazabicyclo[3.3.1]nonan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

5
[ 97483-79-9 ]
9-(benzo[d]thiazol-6-ylsulfonyl)-3-[2-(3,4-dimethoxyphenoxy)ethyl]-3,9-diazabicyclo[3.3.1]nonan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

6
[ 97483-79-9 ]
6-{3-[2-(3,4-dimethoxyphenoxy)ethyl]-2-oxo-3,9-diazabicyclo[3.3.1]nonan-9-ylsulfonyl}benzo[d]thiazol-2(3H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

7
[ 97483-79-9 ]
6-(2-oxo-3,9-diazabicyclo[3.3.1]nonan-9-ylsulfonyl)benzo[d]thiazol-2(3H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

8
[ 97483-79-9 ]
1-(3-ethyl-2-oxo-3,9-diazabicyclo[3.3.1]nonan-9-yl)-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

9
[ 97483-79-9 ]
1-{3-[2-(3,4-dimethoxyphenoxy)ethyl]-2-oxo-3,9-diazabicyclo[3.3.1]nonan-9-yl}-3,3-dimethylpentane-1,2-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

10
[ 97483-79-9 ]
[ 1433825-94-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935
[2]Patent: EP2690102,2014,A1
[3]Patent: WO2014/15993,2014,A1

11
[ 97483-79-9 ]
[ 1433826-00-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935
[2]Patent: EP2690102,2014,A1
[3]Patent: WO2014/15993,2014,A1

12
[ 97483-79-9 ]
benzyl 2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

13
[ 97483-79-9 ]
benzyl 3-(2-(3,4-dimethoxyphenoxy)ethyl)-2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

14
[ 97483-79-9 ]
benzyl 3-ethyl-2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

15
[ 97483-79-9 ]
3-(2-(3,4-dimethoxyphenoxy)ethyl)-3,9-diazabicyclo[3.3.1]nonan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

16
[ 97483-79-9 ]
3-ethyl-3,9-diazabicyclo[3.3.1]nonan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

17
[ 97483-79-9 ]
3,9-diazabicyclo[3.3.1]nonan-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

18
[ 97483-79-9 ]
C₁₇H₂₄N₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935
[2]Patent: EP2690102,2014,A1
[3]Patent: WO2014/15993,2014,A1

19
[ 24424-99-5 ]
[ 97483-79-9 ]
[ 1433825-88-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogen; nickel; In methanol; at 20.0℃; under 760.051 Torr; for 24.0h;Inert atmosphere;	Ethyl 6-cyanopicolinate (7.87g, 44.7mmol) was dissovled in MeOH under argon and degased followed by addition of Boc2O (19.5g, 89mmol), catalytical amount Ni-catalyst and by degasing with argon again. The reaction was stirred under 1 atm H2 at room temperature for 24h, filtered through celite, and concentrated in vacuo. The mixture was purified with flash chromatography in EE/DCM=1:5. TLC [EE/DCM 1:5]: Rf = 0.34. Yield: 8.74g, (68%).
68%	With hydrogen; nickel; In methanol; at 20.0℃; under 760.051 Torr; for 24.0h;Inert atmosphere;	Ethyl 6-cyanopicolinate (7.87g, 44.7mmol) was dissovled in MeOH under argon and degased followed by addition of Boc2O (19.5g, 89mmol), catalytical amount Ni-catalyst and by degasing with argon again. The reaction was stirred under 1 atm H2 at room temperature for 24h, filtered through celite, and concentrated in vacuo. The mixture was purified with flash chromatography in EE/DCM=1:5. TLC [EE/DCM 1:5]: Rf = 0.34. Yield: 8.74g, (68%).

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935
[2]Patent: EP2690102,2014,A1 .Location in patent: Paragraph 0070; 0074
[3]Patent: WO2014/15993,2014,A1 .Location in patent: Page/Page column 35; 36

20
copper(l) cyanide [ No CAS ]
[ 21190-88-5 ]
[ 97483-79-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	for 6h;Reflux; Inert atmosphere;	Solid ethyl 6-bromopicolinate (1 eq., 65.2 mmol, 15.0 g) and cuprous cyanide (2 eq., 130.4 mmol, 11.68g) were added to a 250-mL round bottomed flask equipped with a stir bar. To the round bottomed flask was added anhydrous pyridine (60 mL). Under rapid stirring, the mixture was refluxed under argon for 6 hours. The flask was removed from the hot oil bath, and the black tarry mixture that remained in the flask was diluted with hot toluene (100 mL). To the diluted mixture was added celite powder (-20 g), and the mixture was allowed to stir for -20 minutes to allow the toluene to penetrate the tarry residue, then the celite/tar was filtered through a bed of celite and washed with hot toluene (50 mL). The filtrate was decanted into a 500-mL round bottom flask, and the solvents were removed under reduced pressure to yield a thick, black residue. The residue was redissolved in ethyl acetate (400 mL), and the solution was transferred to a separatory funnel, diluted with 1 M citric acid (300 mL), and the aqueous layer was extracted with ethyl acetate (2 x 200 mL). The combined organic layers were dried over MgS04 and filtered, and concentrated under reduced pressure to yield an orange solid, which was recrystallized from boiling hexanes to yield a white crystalline solid. The white solid was collected by suction filtration, washed with cold hexanes, and dried under high vacuum to give. Yield: 8.23 g (46.7 mmol, 72%). FontWeight="Bold" FontSize="10" H NMR (CDCb, 400 MHz) delta 1.46 (t, J = 7.1 Hz, 3H), 4.52 (q, J= 7.1 Hz, 2H), 7.90 (dd, J= 7.8, 1.1 Hz, 1H), 8.06 (t, J= 7.9 Hz, 1H), 8.34 (dd, J= 8.0, 1.1 Hz, 1H). 13C NMR (CDCb, 100 MHz) delta 14.2, 62.6, 116.3, 127.9, 131.1, 133.9, 138.4, 149.7, 163.5. ESI-MS m/z 111 ([M+H]+, 46%), 149 (90%). ESI- HRMS m/z 111 calc'd for C9H9O2N2 ([M+H]+) 177.0659, found 177.0656

Reference： [1]Patent: WO2018/231843,2018,A1 .Location in patent: Paragraph 0116
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 3922 - 3935

21
[ 97483-79-9 ]
1-(3-(2-(3,4-dimethoxyphenoxy)ethyl)-2-oxo-3,9-diazabicyclo[3.3.1]nonan-9-yl)-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione [ No CAS ]