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[ CAS No. 222986-51-8 ] {[proInfo.proName]}

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Chemical Structure| 222986-51-8
Chemical Structure| 222986-51-8
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Product Details of [ 222986-51-8 ]

CAS No. :222986-51-8 MDL No. :MFCD06801984
Formula : C12H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DAAPYOWCDXFHOC-UHFFFAOYSA-N
M.W : 214.22 Pubchem ID :22709902
Synonyms :

Calculated chemistry of [ 222986-51-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 61.04
TPSA : 76.21 Ų

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) : -6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 2.04
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.494 mg/ml ; 0.00231 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.286 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.56
Solubility : 0.0585 mg/ml ; 0.000273 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 222986-51-8 ]

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

Application In Synthesis of [ 222986-51-8 ]

* 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.

  • Downstream synthetic route of [ 222986-51-8 ]

[ 222986-51-8 ] Synthesis Path-Downstream   1~8

YieldReaction ConditionsOperation in experiment
Referential Example 9 Methyl 4-(2-aminopyridin-5-yl)benzoate In a similar manner to Example 2 except for the use of 5-bromo-2-aminopyridine and 4-carboxyphenyboronic acid as the raw materials instead, the reaction was conducted, whereby 4-(2-aminopyridin-5-yl)benzoic acid was obtained. The resulting 4-(2-aminopyridin-5-yl)benzoic acid (684 mg) was dissolved in methanol (50 ml) at room temperature, followed by the addition of concentrated sulfuric acid (1 ml). After heating under reflux for 2 hours, the reaction mixture was made weakly alkaline with an aqueous solution of sodium bicarbonate. Water and ethyl acetate were added to the resulting mixture to separate the organic layer.
[Referential Example 9] Methyl 4-(2-aminopyridin-5-yl)benzoate In the same manner as in Example 2, a reaction was conducted using 5-bromo-2-aminopyridine and 4-carboxyphenyboronic acid as starting materials, whereby 4-(2-aminopyridin-5-yl)benzoicacid was obtained.
The resulting 4-(2-aminopyridin-5-yl)benzoic acid (684 mg) was dissolved in methanol (50 ml) at room temperature, followed by the addition of concentrated sulfuric acid (1 ml). After heating under reflux for 2 hours, the reaction mixture was made weakly alkaline with an aqueous solution of sodium bicarbonate. Water and ethyl acetate were added to the resulting mixture to separate the organic layer.
  • 2
  • 3-carbamoylbenzene-1,2-diaminium dichloride [ No CAS ]
  • [ 222986-51-8 ]
  • C19H17N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of DMF/pyridine (1:1 v/v) was added compound 2a-z (0.9 mmol) and 1,10-carbonyldiimidazole (CDI) (0.9 mmol) stirred at 60 C under N2 gas atmosphere for 3 h. After the reaction mixture was cooled down to room temperature, 2,3-diaminobenzamide 4 (1 mmol) was added and left to stir overnight until the completion of the reaction as monitored by TLC analysis. Water (100 ml) was added and the resulting product 8 was filtered and dried without further purification.
  • 3
  • 3-carbamoylbenzene-1,2-diaminium dichloride [ No CAS ]
  • [ 222986-51-8 ]
  • 2-(4-(6-aminopyridin-3-yl)phenyl)-1H-benzimidazole-4-carboxamide [ No CAS ]
  • 4
  • [ 222986-51-8 ]
  • cadmium(II) acetate trihydrate [ No CAS ]
  • 2C12H9N2O2(1-)*Cd(2+) [ No CAS ]
  • 5
  • [ 222986-51-8 ]
  • (R)-2-amino-N-(4-chloro-3-(trifluoromethyl)phenyl)propanamide [ No CAS ]
  • (R)-4-(6-aminopyridin-3-yl)-N-(1-((4-chloro-3-(trifluoromethyl)phenyl)amino)-1-oxopropan-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General procedure: In a 100 mL flask, compound 3a (2.5 mmol) was dissolved inanhydrous THF (60 mL), followed by adding 4-methylmorpholine (0.85mL, 7.5 mmol). At 0 C, isobutyl chloroformate (0.55 mL, 3.75 mmol) inanhydrous THF (5 mL) was dropped slowly into the above suspension.Then the reaction mixture was reacted under 0 C for 1 h. Next, the THF(10 mL) solution of compound 9 (0.8 g, 3 mmol) and 4-methylmorpholine(0.85 mL) was added dropwise into the above solution, and stirringwas continued under room temperature overnightTHF was removed invacuo, and the residue was dissolved with EtOAc (60 mL). The organiclayer was washed with water (15 mL), brine (15 mL), dried over Na2SO4.The crude product was purified by column chromatography (PE/EtOAc= 1:1) to get a white solid (0.34 g, 27%).
  • 6
  • [ 222986-51-8 ]
  • tert-butyl-(2R,4R)-4-amino-2-((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
  • (2R,4R)-4-(4-(6-aminopyridin-3-yl)benzamido)-N-(4-chloro-3-(trifluoromethyl)phenyl)pyrrolidine-2-carboxamide [ No CAS ]
  • 7
  • [ 222986-51-8 ]
  • tert-butyl-(2R,4R)-4-amino-2-((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
  • C29H29ClF3N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: In a 100 mL flask, compound 3a (2.5 mmol) was dissolved inanhydrous THF (60 mL), followed by adding 4-methylmorpholine (0.85mL, 7.5 mmol). At 0 C, isobutyl chloroformate (0.55 mL, 3.75 mmol) inanhydrous THF (5 mL) was dropped slowly into the above suspension.Then the reaction mixture was reacted under 0 C for 1 h. Next, the THF(10 mL) solution of compound 9 (0.8 g, 3 mmol) and 4-methylmorpholine(0.85 mL) was added dropwise into the above solution, and stirringwas continued under room temperature overnightTHF was removed invacuo, and the residue was dissolved with EtOAc (60 mL). The organiclayer was washed with water (15 mL), brine (15 mL), dried over Na2SO4.The crude product was purified by column chromatography (PE/EtOAc= 1:1) to get a white solid (0.34 g, 27%). Mp 224-225 C. EI-MS (m/z):505 [M+H]+, 503 [M H] . HRMS (ESI): calcd for [M+H]+C24H21ClF3N4O3: 505.12543, found 505.12735. 1H NMR (400 MHz,DMSO-d6) δ 10.67 (s, 1H), 10.55 (s, 1H), 8.81 (d, J = 6.6 Hz, 1H), 8.74(s, 1H), 8.25 (d, J = 2.4 Hz, 1H), 8.19 (s, 2H), 8.04 (d, J = 8.4 Hz, 2H),7.90 (dd, J = 8.8, 2.3 Hz, 1H), 7.86 (d, J = 8.4 Hz, 2H), 7.69 (d, J = 8.8Hz, 1H), 4.63-4.56 (m, 1H), 2.13 (s, 3H), 1.47 (d, J = 7.2 Hz, 3H). 13CNMR (101 MHz, DMSO-d6) δ 172.71, 169.87, 166.43, 152.33, 146.47,140.07, 139.04, 136.79, 133.08, 132.60, 130.33, 128.85 (2C), 127.63/127.32/ 127.02/126.71 (q, J = 30.3 Hz, Cphenyl-CF3), 126.42 (2C),127.26/124.55/121.84/119.13 (q, J = 273.7 Hz, CF3), 124.44, 124.32,118.33/118.28 (CHphenyl-CF3), 113.61, 50.64, 24.41, 17.89.
  • 8
  • [ 1072-97-5 ]
  • [ 586-76-5 ]
  • [ 222986-51-8 ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; acetonitrile; at 90℃; for 48.0h;Inert atmosphere; General procedure: N-(5-bromopyridin-2-yl)acetamide (1a) (4.30 g, 20 mmol), 4-boronobenzoicacid (3.66 g, 22 mmol), Cs2CO3 (13.0 g, 40 mmol), and Pd(PPh3)4 (1.2 g, 1 mmol) were suspended in a mixture of CH3CN/H2O(200 mL, v/v = 3:2) under N2. The mixture was heated in oil bath at 90C for 48 h. Then the resulting solution was filtered immediately afterthe reaction completed. The filtrate was adjusted to pH4 using HCl aq (6M). The precipitate was filtered out and dried overnight to get theproduct as white solid (3.89 g, 76%). Mp 156-158 C. EI-MS (m/z) 256[M]+.
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