[ CAS No. 872602-74-9 ] {[proInfo.proName]}

Name: 872602-74-9|6-Cyanopicolinic acid|98%
Brand: Ambeed
SKU: A148851
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Quality Control of [ 872602-74-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 872602-74-9 ]

SDS Specification

Alternatived Products of [ 872602-74-9 ]

Product Details of [ 872602-74-9 ]

CAS No. :	872602-74-9	MDL No. :	MFCD10574696
Formula :	C₇H₄N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NDFGHOYJWGPBEH-UHFFFAOYSA-N
M.W :	148.12	Pubchem ID :	21253039
Synonyms :

Calculated chemistry of [ 872602-74-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.91
TPSA :	73.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.68
Log Po/w (XLOGP3) :	0.59
Log Po/w (WLOGP) :	0.65
Log Po/w (MLOGP) :	-1.72
Log Po/w (SILICOS-IT) :	0.69
Consensus Log Po/w :	0.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.47
Solubility :	5.05 mg/ml ; 0.0341 mol/l
Class :	Very soluble
Log S (Ali) :	-1.72
Solubility :	2.84 mg/ml ; 0.0192 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.46
Solubility :	5.09 mg/ml ; 0.0344 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 872602-74-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 872602-74-9 ]

* 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 [ 872602-74-9 ]
Downstream synthetic route of [ 872602-74-9 ]

[ 872602-74-9 ] Synthesis Path-Upstream 1~4

1
[ 97310-93-5 ]
[ 872602-74-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	for 2 h; Heating / reflux	6-Carbamoyl-pyridine-2-carboxylic acid (compound G1) (500 mg, 3 mmol) and phosphorusoxychloride (POCIa) (15 mL) are heated to reflux temperature for 2 h. The mixture is worked up in theusual manner and the crude product is further used without any purification.Yield: 280 mg (63 percent) mp: 180-181 °C
56%	for 4 h; Reflux	6-Carbamoylpicolinic acid (1.0 g, 6.0 mmol) was taken in phosphorus oxychloride (20 mL) and heated to reflux for 4 h. Excess POCl₃ was removed under reduced pressure and the residue was quenched with ice water. The organic product was extracted with EtOAc and the solvent was removed under reduced pressure to afford 6-cyanopicolinic acid (500 mg, yield 56percent), which was carried through without further purification. ¹H NMR (300 MHz, DMSO-d₆) δ 8.31 - 8.28 (m, 2H), 8.26 - 8.21 (m, 1 H). MS (ESI) m/z: Calculated for C₇H₄N₂O₂: 148.03; found: 147.2 (M-H)^-.

Reference： [1] Patent: WO2006/589, 2006, A1, . Location in patent: Page/Page column 57-58
[2] Patent: EP2533783, 2015, B1, . Location in patent: Paragraph 0451-0452

2
[ 50501-38-7 ]
[ 872602-74-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1670 - 1674

3
[ 499-83-2 ]
[ 872602-74-9 ]

Reference： [1] Patent: EP2533783, 2015, B1,

4
[ 125686-90-0 ]
[ 872602-74-9 ]

Reference： [1] Patent: EP2533783, 2015, B1,

[ 872602-74-9 ] Synthesis Path-Downstream 1~19

1
[ 97310-93-5 ]
[ 872602-74-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With trichlorophosphate; for 2.0h;Heating / reflux;	6-Carbamoyl-pyridine-2-carboxylic acid (compound G1) (500 mg, 3 mmol) and phosphorusoxychloride (POCIa) (15 mL) are heated to reflux temperature for 2 h. The mixture is worked up in theusual manner and the crude product is further used without any purification.Yield: 280 mg (63 %) mp: 180-181 C
56%	With trichlorophosphate; for 4.0h;Reflux;	6-Carbamoylpicolinic acid (1.0 g, 6.0 mmol) was taken in phosphorus oxychloride (20 mL) and heated to reflux for 4 h. Excess POCl3 was removed under reduced pressure and the residue was quenched with ice water. The organic product was extracted with EtOAc and the solvent was removed under reduced pressure to afford 6-cyanopicolinic acid (500 mg, yield 56%), which was carried through without further purification. 1H NMR (300 MHz, DMSO-d6) delta 8.31 - 8.28 (m, 2H), 8.26 - 8.21 (m, 1 H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03; found: 147.2 (M-H)-.

Reference： [1]Patent: WO2006/589,2006,A1 .Location in patent: Page/Page column 57-58
[2]Patent: EP2533783,2015,B1 .Location in patent: Paragraph 0451-0452

2
[ 872602-74-9 ]
6-aminomethylpyridine-2-carboxylic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; hydrogen; In ethanol; water; under 2250.23 Torr; for 6.0h;	6-Cyano-pyridine-2-carboxylic acid (compound F2) (250 mg, 1.6 mmol) is dissolved in ethanol (100ml), concentrated hydrochloric acid (1 mL) and Pd/C (150 mg) are added and the mixture ishydrogenated at 3 bar hydrogen pressure for 6 h. The catalyst is filtered of and the crude product istransferred to the next step without any purification. Yield: 255 mg (85 %) mp: 214-221 C

Reference： [1]Patent: WO2006/589,2006,A1 .Location in patent: Page/Page column 57

3
[ 872602-74-9 ]
[ 97310-93-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1670 - 1674

4
[ 50501-38-7 ]
[ 872602-74-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1670 - 1674

5
[ 494769-44-7 ]
[ 872602-74-9 ]
[ 1363397-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 8.0h;	General procedure: The intermediate (3) (0.5 g, 0.00217 mol), EDCl (0.622 g, 0.00325 mol), DMAP (0.345 g, 0.0028 mol) were stirred in dichloromethane (6 mL) at 0 C, and the substituted acid (0.00217 mol) were dissolved in (4 mL) of dichloromethane and charged to the reaction mixture and stirred at room temperature for 8 h. The reaction completion was monitored by TLC. Reaction was completed. The reaction mixture was diluted with (10 mL) of dichloromethane, and was washed with 10% NaHCO3 (10 mL). Separated the organic layer and was washed with saturated brine solution (10 mL). The organic layer was dried over sodium sulfate and concentrated the organic layer under reduced pressure to afford compounds 4a-t. The spectral data of compounds 4(a-t) are given below.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 49,p. 172 - 182

6
[ 499-83-2 ]
[ 872602-74-9 ]

Reference： [1]Patent: EP2533783,2015,B1

7
[ 125686-90-0 ]
[ 872602-74-9 ]

Reference： [1]Patent: EP2533783,2015,B1

8
[ 97483-79-9 ]
[ 872602-74-9 ]