Home Cart 0 Sign in  

[ CAS No. 22282-72-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 22282-72-0
Chemical Structure| 22282-72-0
Structure of 22282-72-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 22282-72-0 ]

Related Doc. of [ 22282-72-0 ]

Alternatived Products of [ 22282-72-0 ]

Product Details of [ 22282-72-0 ]

CAS No. :22282-72-0 MDL No. :MFCD01318566
Formula : C6H5NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BXHCJLRTXPHUGH-UHFFFAOYSA-N
M.W : 139.11 Pubchem ID :280756
Synonyms :

Calculated chemistry of [ 22282-72-0 ]

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 : 2.0
Molar Refractivity : 34.02
TPSA : 70.16 Ų

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) : -7.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.62
Log Po/w (XLOGP3) : -0.55
Log Po/w (WLOGP) : 0.07
Log Po/w (MLOGP) : -0.15
Log Po/w (SILICOS-IT) : 0.89
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) : -0.73
Solubility : 25.7 mg/ml ; 0.185 mol/l
Class : Very soluble
Log S (Ali) : -0.45
Solubility : 48.9 mg/ml ; 0.352 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.28
Solubility : 7.33 mg/ml ; 0.0527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 22282-72-0 ]

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

Application In Synthesis of [ 22282-72-0 ]

* 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 [ 22282-72-0 ]
  • Downstream synthetic route of [ 22282-72-0 ]

[ 22282-72-0 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 55-22-1 ]
  • [ 22282-72-0 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 35, p. 4389 - 4392
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 15, p. 2253 - 2261
[3] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
  • 2
  • [ 6313-54-8 ]
  • [ 22282-72-0 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 25, p. 9420 - 9430
[2] Helvetica Chimica Acta, 1951, vol. 34, p. 496,499
  • 3
  • [ 55-22-1 ]
  • [ 22282-72-0 ]
  • [ 99-11-6 ]
Reference: [1] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
[2] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
[3] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
  • 4
  • [ 91940-86-2 ]
  • [ 22282-72-0 ]
Reference: [1] Bl. nation. hyg. Labor. Tokyo, 1956, vol. 74, p. 115,117[2] Chem.Abstr., 1957, p. 8740
  • 5
  • [ 13362-28-2 ]
  • [ 22282-72-0 ]
Reference: [1] Helvetica Chimica Acta, 1951, vol. 34, p. 496,499
  • 6
  • [ 10386-27-3 ]
  • [ 22282-72-0 ]
Reference: [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407
  • 7
  • [ 72716-86-0 ]
  • [ 22282-72-0 ]
Reference: [1] Roczniki Chemii, 1959, vol. 33, p. 1343,1345[2] Chem.Abstr., 1960, p. 13123
  • 8
  • [ 20265-39-8 ]
  • [ 22282-72-0 ]
Reference: [1] Roczniki Chemii, 1959, vol. 33, p. 1343,1345[2] Chem.Abstr., 1960, p. 13123
  • 9
  • [ 14305-17-0 ]
  • [ 22282-72-0 ]
Reference: [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407
  • 10
  • [ 7598-35-8 ]
  • [ 22282-72-0 ]
Reference: [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407
  • 11
  • [ 52092-43-0 ]
  • [ 22282-72-0 ]
Reference: [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407
  • 12
  • [ 22282-72-0 ]
  • [ 33972-97-3 ]
Reference: [1] Patent: WO2013/97773, 2013, A1,
  • 13
  • [ 22282-72-0 ]
  • [ 74-88-4 ]
  • [ 26156-51-4 ]
Reference: [1] Patent: WO2011/25851, 2011, A1, . Location in patent: Page/Page column 71
[2] Patent: US9284312, 2016, B2,
  • 14
  • [ 55-22-1 ]
  • [ 22282-72-0 ]
  • [ 99-11-6 ]
Reference: [1] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
[2] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
[3] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 9-10
  • 15
  • [ 22282-72-0 ]
  • [ 24537-50-6 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen; palladium(II) hydroxide In methanol at 20℃; for 18 h; Autoclave To a stirred solution of 2-oxo-l,2-dihydropyridine-4-carboxylic acid (SMI) (500 g, 3.59 mol) in methanol (10 L) was added palladium hydroxide (150 g) into a 20 L autoclave under N2 atmosphere. The reaction mixture was stirred under atmosphere (5 kg/ cm2) at RT for 18 h. After consumption of the starting material (monitored by LCMS), the reaction mixture was filtered through a pad of celite and concentrated under reduced pressure. Obtained reside was triturated with diethyl ether (2.5 L) and dried under vacuum to afford compound 1 (450 g, 85 percent) as off white solid. 1H NMR (500 MHz, DMSO-d6): δ 12.37 (s, 1H), 7.44 (s, 1H), 3.16-3.12 (m, 2H), 2.78-2.71 (m, 1H), 2.33-2.21 (m, 2H), 1.98-1.92 (m, 1H), 1.74-1.63 (m, 1H). LCMS (m/z): 144.2 [M++1].
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 46, p. 6486 - 6493
[2] Patent: WO2018/26798, 2018, A1, . Location in patent: Page/Page column 33; 34
[3] Patent: US2007/191406, 2007, A1, . Location in patent: Page/Page column 27
  • 16
  • [ 22282-72-0 ]
  • [ 24537-50-6 ]
YieldReaction ConditionsOperation in experiment
38 g With palladium 10% on activated carbon; hydrogen In methanol at 30℃; for 24 h; A solution of 2-hydroxypyridine-4-carboxylic acid (40.0 g) and 10percent palladium hydroxide/carbon (8.0 g) in methanol (500 mL) was stirred at 30°C for 24 hr under a hydrogen atmosphere (50 psi) . The reaction mixture was filtered, the catalyst was removed, and the filtrate was concentrated under reduced pressure to give the title compound (38.0 g) .XH NMR (400 MHz, CDC13) δ 1.64-1.73 (1H, m) , 1.92-1.99 (1H, m) , 2.20-2.32 (2H, m) , 2.71-2.78 (1H, m) , 3.11-3.17 (2H, m) , 7.50 (1H, s) , 12.49 (1H, brs) .MS (ESI+) : [M-l]+ 142.
Reference: [1] Patent: WO2013/18929, 2013, A1, . Location in patent: Paragraph 0532
  • 17
  • [ 67-56-1 ]
  • [ 22282-72-0 ]
  • [ 89937-77-9 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: at 0 - 20℃;
Stage #2: With hydrogenchloride In acetic acid methyl ester at 20℃; for 16 h;
A. Methyl 2-oxo-l,2-dihydropyridine-4-carboxylate[0095] To MeOH (80 mL) at 00C was slowly added acetyl chloride (20.45 mL, 288 mmol) while stirring. The resulting solution was allowed to warm to RT and stirred for 30 min. To the resulting HCl/MeOH/MeOAc solution was added 2- hydroxyisonicotinic acid (4.00 g, 28.8 mmol) in one portion, and the mixture was stirred at ambient temperature for 16h. The mixture was concentrated and the residue was stripped from MeOH (10 mL). The crude product was purified by chromatography (silica gel 230-400 mesh, solvent gradient 0-20percent MeOH/CH2Cl2) to afford IA (3.40 g, 22.20 mmol, 77 percent yield) as a yellow solid. LC-MS, [M + H]+ = 154.
3.5 g at 0 - 20℃; Example 170 1- (2-Cyclopropyl-3-methylimidazo [1, 2-a] pyridin-6-yl) -4- ( (4- fluorophenoxy) methyl) pyridin-2 ( 1H) -one A) Methyl 2-oxo-l, 2-dihydropyridine-4-carboxylate To a stirred solution of 2-hydroxypyridine-4-carboxylic acid (5.0 g) in MeOH (50 ml) was added acetyl chloride (26 ml) dropwise at 0°C over 15 min. The reaction mixture was slowly warmed to room temperature, and stirred for 20 h. The reaction mixture was concentrated in vacuo, and diluted with EtOAc and water. The organic layer was washed with saturated NaHCC>3 solution, concentrated in vacuo, and purified by column chromatography (MeOH/DCM) to afford the title compound (3.5 g) as an off-white solid. MS (ESI+) : [M+H]+ 154.0.
Reference: [1] Patent: WO2010/104830, 2010, A1, . Location in patent: Page/Page column 70-71
[2] Patent: WO2013/105676, 2013, A1, . Location in patent: Page/Page column 220; 221
  • 18
  • [ 67-56-1 ]
  • [ 22282-72-0 ]
  • [ 89937-77-9 ]
Reference: [1] Patent: WO2018/149419, 2018, A1, . Location in patent: Paragraph 00909
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 12, p. 4022 - 4036
[3] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0241
[4] Patent: WO2017/222952, 2017, A1, . Location in patent: Page/Page column 37; 38
  • 19
  • [ 22282-72-0 ]
  • [ 25504-47-6 ]
Reference: [1] Patent: WO2018/26798, 2018, A1,
  • 20
  • [ 22282-72-0 ]
  • [ 127838-58-8 ]
Reference: [1] Patent: WO2013/192125, 2013, A1, . Location in patent: Page/Page column 130
  • 21
  • [ 22282-72-0 ]
  • [ 123148-66-3 ]
Reference: [1] Patent: WO2011/25851, 2011, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 22282-72-0 ]

Alcohols

Chemical Structure| 86454-13-9

[ 86454-13-9 ]

2-Hydroxy-6-methylisonicotinic acid

Similarity: 0.93

Chemical Structure| 188554-13-4

[ 188554-13-4 ]

2-Hydroxyisonicotinaldehyde

Similarity: 0.84

Chemical Structure| 913836-16-5

[ 913836-16-5 ]

5-Bromo-2-hydroxyisonicotinic acid

Similarity: 0.83

Chemical Structure| 913836-17-6

[ 913836-17-6 ]

Methyl 5-bromo-2-hydroxyisonicotinate

Similarity: 0.79

Chemical Structure| 10128-71-9

[ 10128-71-9 ]

3-Hydroxyisonicotinic acid

Similarity: 0.75

Carboxylic Acids

Chemical Structure| 86454-13-9

[ 86454-13-9 ]

2-Hydroxy-6-methylisonicotinic acid

Similarity: 0.93

Chemical Structure| 105596-63-2

[ 105596-63-2 ]

2-Methoxyisonicotinic acid

Similarity: 0.92

Chemical Structure| 55-22-1

[ 55-22-1 ]

4-Pyridinecarboxylic acid

Similarity: 0.84

Chemical Structure| 913836-16-5

[ 913836-16-5 ]

5-Bromo-2-hydroxyisonicotinic acid

Similarity: 0.83

Chemical Structure| 1211581-22-4

[ 1211581-22-4 ]

2-Methoxy-3-methylisonicotinic acid

Similarity: 0.83

Related Parent Nucleus of
[ 22282-72-0 ]

Pyridines

Chemical Structure| 86454-13-9

[ 86454-13-9 ]

2-Hydroxy-6-methylisonicotinic acid

Similarity: 0.93

Chemical Structure| 105596-63-2

[ 105596-63-2 ]

2-Methoxyisonicotinic acid

Similarity: 0.92

Chemical Structure| 26156-51-4

[ 26156-51-4 ]

Methyl 2-methoxyisonicotinate

Similarity: 0.87

Chemical Structure| 105596-61-0

[ 105596-61-0 ]

Ethyl 2-methoxyisonicotinate

Similarity: 0.85

Chemical Structure| 55-22-1

[ 55-22-1 ]

4-Pyridinecarboxylic acid

Similarity: 0.84