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Chemistry
Heterocyclic Building Blocks
Pyridines
2-Chloro-N-phenylisonicotinamide
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Pyridines
Aryls Amines Chlorides Amides
Alternatived Products of [ 80194-83-8 ]
Product Citations

Product Details of [ 80194-83-8 ]

CAS No. :80194-83-8 MDL No. :MFCD09817650
Formula : C12H9ClN2O Boiling Point : No data available
Linear Structure Formula :- InChI Key :LTAXNWGTCKPZGT-UHFFFAOYSA-N
M.W : 232.67 Pubchem ID :15075715
Synonyms :

Calculated chemistry of [ 80194-83-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.46
TPSA : 41.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 3.47
Log Po/w (WLOGP) : 2.8
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 2.69
Consensus Log Po/w : 2.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.0348 mg/ml ; 0.000149 mol/l
Class : Soluble
Log S (Ali) : -4.03
Solubility : 0.0215 mg/ml ; 0.0000925 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.17
Solubility : 0.00159 mg/ml ; 0.00000684 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 80194-83-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 80194-83-8 ]

* 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 [ 80194-83-8 ]

[ 80194-83-8 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 65287-34-5 ]
  • [ 62-53-3 ]
  • [ 80194-83-8 ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 0 - 95℃; for 2 h; To the sol. of 2-chloroisonicotinoyl chloride (Anderson, W. K. , Dean, D. C. , Endo, T., J Med Chem., 1990,33, 1667,10 g, 56.8 mmol) in 1,2-dichloroethane (100 mL) was added at 0 °C a sol. of aniline (5.70 mL, 62.5 mmol) and DIPEA (10.2 ml, 59.6 mmol) in 1,2-dichloroethane (10 ml) during ca. 30 min. The reaction was stirred at 0 °C for ca. 30 min and subsequently for 1 h at 95 °C. Water (30 mL) was added at rt and the mixture was filtered-off. The filtrate was extracted with CH2Cl2 (200 mL). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. The residue was crystallized from MeOH/water 1: 10 (110 mL), yielding the title compound (12.12 g, 92percent). LC-MS: RT = 0.87 min; ES+ = 233.1.
92% With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 0 - 95℃; for 2 h; 2-Chloro-N-phenylisonicotinamide (N); To the sol. of 2-chloro-isonicotinoyl chloride (Anderson, W. K. , Dean, D. C. , Endo, T., J. Med. Chem., 1990, 33, 1667,10 g, 56.8 mmol) in 1,2-dichloroethane (100 mL) was added at 0 °C a sol. of aniline (5.70 mL, 62.5 mmol) and DIPEA (10.2 ml, 59.6 mmol) in 1,2- dichloroethane (10 ml) during ca. 30 min. The reaction was stirred at 0 °C for ca. 30 min and subsequently for 1 h at 95 °C. Water (30 mL) was added at rt and the mixture was filtered-off. The filtrate was extracted with CH2CI2 (200 mL). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. The residue was crystallized from MeOH/water 1: 10 (110 mL), yielding the title compound (12.12 g, 92percent). LC-MS: RT = 0.87 min; ES+ = 233.1
92% With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 0 - 95℃; for 2 h; 2-Chloro-N-phenylisonicotinamide (N) To the sol. of 2-chloro-isonicotinoyl chloride (Anderson, W. K. , Dean, D. C. , Endo, T., J. Med. Chem., 1990,33, 1667,10 g, 56. 8 mmol) in 1,2-dichloroethane (100 mL) was added at 0 °C a sol. of aniline (5.70 mL, 62.5 mmol) and DIPEA (10.2 ml, 59.6 mmol) in 1,2- dichloroethane (10 ml) during ca. 30 min. The reaction was stirred at 0 °C for ca. 30 min and subsequently for 1 h at 95 °C. Water (30 mL) was added at rt and the mixture was filtered-off. The filtrate was extracted with CH2C12 (200 mL). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. The residue was crystallized from MeOH/water 1: 10 (110 mL), yielding the title compound (12.12 g, 92percent). LC-MS: RT = 0.87 min; ES+ = 233.1.
92% With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 0 - 95℃; for 2 h; 2-Chloro-N-phenylisonicotinamide (N) To the sol. of 2-chloro-isonicotinoyl chloride (Anderson, W. K., Dean, D. C., Endo, T., J Med Chem., 1990, 33, 1667,10 g, 56. 8 mmol) in 1,2-dichloroethane (100 mL) was added at 0 °C a sol. of aniline (5.70 mL, 62.5 mmol) and DIPEA (10.2 ml, 59.6 mmol) in 1,2-dichloroethane (10 ml) during ca. 30 min. The reaction was stirred at 0 °C for ca. 30 min and subsequently for 1 h at 95 °C. Water (30 mL) was added at rt and the mixture was filtered-off. The filtrate was extracted with CH2Cl2 (200 mL). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. The residue was crystallized from MeOH/water 1: 10 (110 mL), yielding the title compound (12.12 g, 92percent). LC-MS: RT = 0. 87 min; ES+ = 233.1.
92% at 0 - 95℃; for 2 h; 2-Chloro-N-phenylisonicotinamide (N); To the sol. of 2-chloro-isonicotinoyl chloride (Anderson, W. K., Dean, D. C. , Endo, T., J Med. Chem., 1990, 33, 1667,10 g, 56. 8 mmol) in 1,2-dichloroethane (100 mL) was added at 0 °C a sol. of aniline (5.70 mL, 62.5 mmol) and DIPEA (10.2 ml, 59.6 mmol) in 1,2- dichloroethane (10 ml) during ca. 30 min. The reaction was stirred at 0 °C for ca. 30 min and subsequently for 1 h at 95 °C. Water (30 mL) was added at rt and the mixture was filtered-off. The filtrate was extracted with CH2C12 (200 mL). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. The residue was crystallized from MeOH/water 1: 10 (110 mL), yielding the title compound (12.12 g, 92percent). LC-MS: RT = 0.87 min; ES+ = 233. 1.

Reference： [1] Patent: WO2005/40120, 2005, A1, . Location in patent: Page/Page column 23
[2] Patent: WO2005/40165, 2005, A1, . Location in patent: Page/Page column 22
[3] Patent: WO2005/40173, 2005, A1, . Location in patent: Page/Page column 33-34
[4] Patent: WO2005/54243, 2005, A1, . Location in patent: Page/Page column 24-25
[5] Patent: WO2005/54244, 2005, A2, . Location in patent: Page/Page column 23
[6] Patent: WO2012/142513, 2012, A1, . Location in patent: Page/Page column 426-427
  • 2
  • [ 201230-82-2 ]
  • [ 62-53-3 ]
  • [ 80194-83-8 ]
YieldReaction ConditionsOperation in experiment
36% With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 46 h; Autoclave General procedure: In a typical experiment, Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.1 mg, 0.05 mmol), 2,5-diiodopyridine(331 mg, 1 mmol), 2,3-diiodopyridine (331 mg, 1 mmol) or 2-chloro-3,4-diiodopyridine (182.75 mg, 0.5 mmol), amine nucleophile (see above in the tables; 3 mmol of a/2 mmol of b/1.5 mmol of c,d/1.1 mmol of e,f,g,h) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL autoclave. The atmosphere was changed to carbon monoxide and the autoclave was pressurized to the given pressure by carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C andanalysed by GC-MS (internal standard: naphthalene). The mixture was then concentrated and evaporated to dryness and worked-up as described in Section 4.2.
Reference： [1] Tetrahedron, 2017, vol. 73, # 15, p. 2131 - 2138
  • 3
  • [ 14178-44-0 ]
  • [ 80194-83-8 ]
Reference： [1] Tetrahedron, 1989, vol. 45, # 23, p. 7469 - 7476
  • 4
  • [ 6313-54-8 ]
  • [ 80194-83-8 ]
Reference： [1] Patent: WO2012/142513, 2012, A1,
  • 5
  • [ 55-22-1 ]
  • [ 80194-83-8 ]
Reference： [1] Tetrahedron, 1989, vol. 45, # 23, p. 7469 - 7476
  • 6
  • [ 14254-57-0 ]
  • [ 80194-83-8 ]
Reference： [1] Tetrahedron, 1989, vol. 45, # 23, p. 7469 - 7476
  • 7
  • [ 3034-31-9 ]
  • [ 80194-83-8 ]
Reference： [1] Tetrahedron, 1989, vol. 45, # 23, p. 7469 - 7476

Tags: 80194-83-8 synthesis path| 80194-83-8 SDS| 80194-83-8 COA| 80194-83-8 purity| 80194-83-8 application| 80194-83-8 NMR| 80194-83-8 COA| 80194-83-8 structure

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction
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; ;