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[ CAS No. 10222-62-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 10222-62-5
Chemical Structure| 10222-62-5
Chemical Structure| 10222-62-5
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Product Details of [ 10222-62-5 ]

CAS No. :10222-62-5 MDL No. :MFCD01550057
Formula : C11H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZMHKFJMROFPASK-UHFFFAOYSA-N
M.W : 203.19 Pubchem ID :1130354
Synonyms :

Calculated chemistry of [ 10222-62-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.19
TPSA : 59.42 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 2.63
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 1.8
Consensus Log Po/w : 1.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -3.12
Solubility : 0.155 mg/ml ; 0.000762 mol/l
Class : Soluble
Log S (Ali) : -3.53
Solubility : 0.0602 mg/ml ; 0.000296 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.21
Solubility : 0.126 mg/ml ; 0.000619 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 10222-62-5 ]

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 [ 10222-62-5 ]

* 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 [ 10222-62-5 ]

[ 10222-62-5 ] Synthesis Path-Downstream   1~22

  • 2
  • [ 115801-85-9 ]
  • [ 10222-62-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In 1,4-dioxane; water for 0.5h; Ambient temperature;
YieldReaction ConditionsOperation in experiment
86% R.2 2-Methoxyquinoline-4-carboxylic acid The resulting compound (1.82 g) was dissolved in 60 ml of methanol, 9 ml of 2N aqueous solution of sodium hydroxide was added thereto, the mixture was stirred for 2 hours at room temperature, methanol was evaporated therefrom in vacuo, the residue was dissolved in 100 ml of water, the solution was washed with ether, adjusted to pH 4 with 10% hydrochloric acid, the crystals separated out therefrom were collected by filtration, washed with water, dried in vacuo, and 2-methoxyquinoline-4-carboxylic acid in colourless crystals was prepared in 86% yield. M.p. 185°-186° C.
4% R.5 2-Methoxy-4-quinolinecarboxylic acid (Compound i) REFERENCE EXAMPLE 5 2-Methoxy-4-quinolinecarboxylic acid (Compound i) Compound i was obtained (yield3 4%, yield4 100%) in a manner similar to Reference Example 1, except for using methyl iodide in place of n-butyl iodide.
2-Chlor-chinolin-4-carbonsaeure, entspr. Na-Alkoholat;
  • 4
  • [ 124-41-4 ]
  • [ 10222-62-5 ]
YieldReaction ConditionsOperation in experiment
beim Erhitzen ueber den Schmelzpunkt;
  • 6
  • [ 10222-62-5 ]
  • endo-8-methyl-8-azabicyclo<3.2.1>oct-3-yl 2-methoxy-4-quinolinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / 0.5 h / Heating 2: 1.) 15percent n-BuLi / 1.) hexane, THF, 0 deg C, 15 min, 2.) hexane, THF, 0 deg C, 1 h
  • 7
  • [ 10222-62-5 ]
  • 2-methoxy-quinoline-4-carboxylic acid-(2-morpholino-ethyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene; SOCl2 / 60 °C
  • 8
  • [ 10222-62-5 ]
  • 2-methoxy-quinoline-4-carboxylic acid-(3-morpholino-propyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene; SOCl2 / 60 °C 2: benzene
  • 9
  • [ 10222-62-5 ]
  • 1-methyl-1H-pyrrole-2-carboxylic acid ((S)-3-methylamino-4-phenylbutyl)amide hydrochloride [ No CAS ]
  • [ 1312556-94-7 ]
YieldReaction ConditionsOperation in experiment
58% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; 1.8 Example 1.7: f S)-N.1 ,5-trimethyl-N-(4-(1 -methvl-1 H-pyrrole-2-carboxamido)-1 - phenylbutan-2-yl)-1H-indazole-3-carboxamide1-Methyl-1 H-pyrrole-2-carboxylic acid ((S)-3-methylamino-4-phenyl-butyl)-amide hydrochloride (100 mg, 0.31 mmol), 1 ,5-dimethyl-1H-indazole-3-carboxylic acid (59 mg, 0.31 mmol), HOBt (71 mg, 0.476 mmol), EDC x HCI (72 mg, 0.37 mmol), and triethylamine (0.108 ml, 0.78 mmol) were dissolved in DCM (5 ml) and stirred at rt for 5 h. The mixture was concentrated, redissolved in EtOAc, washed with sat. NaHCCv and NaCI-soln., dried (Na2S04), filtered and concentrated. The crude product was purified by chromatography (Biotage, DCM to DCM:MeOH 95:5 over 10 min) to yield 131 mg (90 %) of the title compound as white solid. [1 H-NMR (DMSO, 600 MHz, rotamers) 7.93 (d, 1H), 7.53 (dd, 1 H), 7.33-7.28 (m, 3H), 7.26-7.19 (m, 2H), 7.11-7.04 (m, 2H), 6.86 (d, 1 H), 6.67 (d, 1H), 5.98 (d, 1H), 5.10-5.02 (m, 1H), 4.04, 3.95 (2s, 3H), 3.82, 3.70 (2s, 3H), 3.05, 2.98 (2s, 3H), 3.24- 3.16 (m, 1H), 3.00-2.95 (m, 1H), 2.91-2.88 (m, 2H), 2.36 (s, 3H), 1.94-1.63 (m, 2H); UPLCMS Rt, = 1.29 min; [M+H]+ = 458.3].
  • 10
  • [ 10222-62-5 ]
  • [ 1617517-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.17 h / Reflux 1.2: 5 h / Reflux 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / Reflux
  • 11
  • [ 10222-62-5 ]
  • [ 109-64-8 ]
  • [ 1617517-81-3 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 2-methoxyquinoline-4-carboxylic acid; 1,3-dibromo-propane In tetrahydrofuran for 0.166667h; Reflux; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 5h; Reflux; 4.1.2 3-Bromopropyl 2-methoxyquinoline-4-carboxylate A mixture of commercially available compound 9 (Aldrich, USA, 0.20g, 0.98mmol) in dry THF (15mL) containing 1,3-dibromopropane (1.0mL, 9.85mmol) was heated under reflux for 10min and DBU (0.15mL, 0.98mmol) was then added dropwise. The reaction mixture was heated under reflux for 5h and then concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. Purification of the residue by flash chromatography with dichloromethane as the eluent gave pure compound 10 (0.22g, yield 69%) as a yellow oil. 1H NMR (400MHz, CDCl3): 2.36 (m, 2H), 3.55 (t, J=6.4, 2H), 4.09 (s, 3H), 4.56 (t, J=6.1, 2H), 7.40-7.48 (m, 2H), 7.66 (t, J=7.7, 1H), 7.89 (d, J=8.4, 1H), 8.57 (d, J=8.4, 1H). MS (ESI): m/z 324, 326 (M+H+).
  • 12
  • [ 3529-08-6 ]
  • [ 10222-62-5 ]
  • [ 1617517-73-3 ]
YieldReaction ConditionsOperation in experiment
55% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h; A mixture of commercially available compound 9 (0.25g, 1.23mmol) in dry DMF (10mL) containing BOP (0.54g, 1.22mmol), TEA (0.52mL, 3.7mmol), and <strong>[3529-08-6]1-(3-aminopropyl)piperidine</strong> (0.29mL, 1.82mmol) was stirred at room temperature for 3h. The reaction mixture was then concentrated under reduced pressure and the residue was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. Purification of the residue by flash chromatography with ethyl acetate/triethylamine (9:1) as the eluent gave pure compound 7b (0.22g, yield 55%) as a yellow oil, which crystallized on standing. An analytical sample was obtained by recrystallization from n-hexane-diethyl ether (mp 84-85C). 1H NMR (400MHz, CDCl3): 1.23-1.31 (m, 6H), 1.76-1.82 (m, 2H), 2.35 (br s, 4H), 2.49-2.52 (m, 2H), 3.62 (q, J=5.7, 2H), 4.07 (s, 3H), 6.98 (s, 1H), 7.40 (t, J=7.0, 1H), 7.63 (t, J=7.2, 1H), 7.85 (d, J=8.4, 1H), 8.18 (d, J=8.4, 1H), 8.70 (br s, 1H). 13C NMR (100MHz, CDCl3): 24.0, 24.1, 25.8, 41.1, 53.5, 54.6, 59.0, 110.9, 121.8, 124.6, 125.5, 127.5, 129.9, 145.6, 147.3, 161.7, 166.8. HRMS (ESI): m/z calculated for [C19H25N3O2+H+] requires 328.2020, found 328.2020.
  • 13
  • [ 10222-62-5 ]
  • 1-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-amine [ No CAS ]
  • N-[1-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-2-methoxyquinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 2h; 27 N-[1-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-2-methoxyquinoline-4-carboxamide ExampLe I2-methoxy-N-[ 1- (4-methoxybenzyl)-3, 5-dimethyl- I H-pyrazol-4-yI]quinoline-4- carboxamide 50 mg (0.22 mmcl) I -(4-methoxybenzy[)-3,5-dimethy[-1 H-pyrazo[-4-amine(intermediate 11C) was dissoLved in 5 mL tetrahydrofuran and 52 mg (0.26 mmol) 2- methoxyquinoLine-4-carboxylic acid, 56 pL ( 0.32 mmol) N,N-diisopropylethylamine and 104 mg (0.32 mmol) TBTU were added. The reaction mixture was stirred for 24 hat 25°C. After evaporation the residue was dissolved in 2.5 mL dimethy[formamide and purified via preparative HPLC (method 3) to obtain 61 mg (0.14 mmol, 66%) of the desired title compound after drying.ExampLe 192-cyclopropyl-N-[ I -(4-fluorobenzyl)- 3, 5-dimethyl- I H-pyrazol-4-yI]quinoline-4-carboxamide_N-[1-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-2-methoxyquinoline-4-carboxamide In analogy to example 1 ), 150 mg (0.68 mmol) 1 -(4-fluorobenzyl)-3,5-dimethyl-1 H-pyrazol-4-amine (intermediate 1C) was stirred with 167 mg (0.82 mmol) 2-methoxyquinoline-4-carboxylic acid, 179 μL (1.03 mmol) N,N-diisopropylethylamine and 329 mg (1.03 mmol) TBTU in 5 mL tetrahydrofuran for 2 h at 25° C. The reaction mixture was evaporated and the residue partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted two further times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated The residue was dissolved indichloromethane and under evaporation adsorbed on Isolute HM-N (Biotage). The isolute was given on a Biotage SNAP cartridge (25 g; KP-Sil) preequilibrated with hexane and purified via column chromatography on silica gel (solvent: hexane/ 0- 100% ethyl acetate ). The resulting crude product was again purified via preparative HPLC (method 3) to obtain 228 mg (0.56 mmol, 82%) of the desired title compound .1 H NMR (300 MHz, DMSO d6): δ (ppm) = 2.13 (s, 3 H), 2.17 (s, 3 H), 4.04 (s, 3 H), 5.24 (s, 2 H), 7.11 - 7.30 (m, 5 H), 7.44 - 7.56 (m, 1 H), 7.66 - 7.78 (m, 1 H), 7.82 - 7.91 (m, 1 H), 8.00 - 8.10 (m, 1 H), 9.91 (s, 1 H).
  • 14
  • [ 10222-62-5 ]
  • 1-(4-methoxybenzyl)-3,5-dimethyl-1H-pyrazol-4-amine [ No CAS ]
  • 2-methoxy-N-[1-(4-methoxybenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]quinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 24h; 1 ExampLe I2-methoxy-N-[ 1- (4-methoxybenzyl)-3, 5-dimethyl- I H-pyrazol-4-yI]quinoline-4- carboxamide ExampLe I2-methoxy-N-[ 1- (4-methoxybenzyl)-3, 5-dimethyl- I H-pyrazol-4-yI]quinoline-4- carboxamide 50 mg (0.22 mmcl) I -(4-methoxybenzy[)-3,5-dimethy[-1 H-pyrazo[-4-amine(intermediate 11C) was dissoLved in 5 mL tetrahydrofuran and 52 mg (0.26 mmol) 2- methoxyquinoLine-4-carboxylic acid, 56 pL ( 0.32 mmol) N,N-diisopropylethylamine and 104 mg (0.32 mmol) TBTU were added. The reaction mixture was stirred for 24 hat 25°C. After evaporation the residue was dissolved in 2.5 mL dimethy[formamide and purified via preparative HPLC (method 3) to obtain 61 mg (0.14 mmol, 66%) of the desired title compound after drying.1H NMR (300MHz, DMSO d6): O (ppm) = 2.12 (s, 3 H), 2.16 (s, 3 H), 3.73 (s, 3 H), 4.04(s, 3 H), 5.16 (s, 2 H), 6.91 (d, 2 H), 7.14 (d, 2 H), 7.21 (s, I H), 7.47 - 7.55 (m, I H),7.69 - 7.77 (m, I H), 7.83 - 7.89 (m, I H), 8.01 - 8.08 (m, I H), 9.88 (s, I H).
  • 15
  • [ 10222-62-5 ]
  • [ 148703-15-5 ]
  • (1-butylpiperidin-4-yl)methyl 2-methoxyquinoline-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-methoxyquinoline-4-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 40℃; for 1h; Stage #2: N-butyl-4-hydroxymethyl-piperidine With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 50℃; for 1h;
  • 16
  • [ 10222-62-5 ]
  • [ 65017-57-4 ]
  • N-[(1-butylpiperidin-4-yl)methyl]-2-methoxyquinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;
  • 17
  • [ 27578-60-5 ]
  • [ 10222-62-5 ]
  • 2-methoxy-N-[2-(piperidin-1-yl)ethyl]quinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% Stage #1: 2-methoxyquinoline-4-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.25h; Stage #2: 1-(2-aminoethyl)piperidine In dichloromethane at 20℃;
  • 18
  • [ 10222-62-5 ]
  • [ 106-93-4 ]
  • 2-bromoethyl 2-methoxyquinoline-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 5h; Reflux;
  • 19
  • [ 10222-62-5 ]
  • 2-(piperidin-1-yl)ethyl 2-methoxyquinoline-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 5 h / Reflux 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 h / Reflux
  • 20
  • [ 10222-62-5 ]
  • 2-[4-(hydroxymethyl)piperidin-1-yl]ethyl 2-methoxyquinoline-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 5 h / Reflux 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 6 h / Reflux
  • 21
  • [ 10222-62-5 ]
  • [ 1198001-03-4 ]
  • 2’-(tert-butyl)-1-(2-methoxyquinoline-4-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12.5h; 19 2'-(tert-butyl)-1-(2-methoxyquinoline-4-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyridine Azole)-7'(6'H)-one (I19) According to the method of Example 1, the compound 2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'( 6'H)-ketone.Under ice bath conditions, 2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'(6'H )-Ketone (400mg, 1.1mmol), HATU (458mg, 1.2mmol), triethylamine (0.2ml, 1.2mmol) were dissolved in 10mL DMF, stirred at 0 for 0.5h, then added 2-methoxyquinoline-4 -Carboxylic acid (1mmol, 204mg), react at room temperature for 12h; add the reaction solution to 50mL ice water, extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure, the crude product is purified by silica gel column chromatography Title Compound I19
65% With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h; 4.1.1. General procedure for the preparation of 7a~7u General procedure: (A) Pyruvic aldehyde (2, 25 mmol) was added dropwise to asolution of 1 (30 mmol) in H2O (100 mL), and after stirring atroom temperature for 2 h, the mixture was extracted withCH2Cl2, dried with anhydrous Na2SO4, and concentrated invacuo to afford hydrazine 3. Then, a 40% aqueous solution ofglyoxal (25 mL) was added to a solution of 3 (62 mmol) inH2O (100 mL). The mixture was heated at reflux for 5 h andextracted with ethyl acetate. The organic phase was dried,filtered, and concentrated to give 4 as yellow solid. Tetrahydropyrrole(8 mmol) was added to a solution of 4 (24 mmol)in MeOH (45 mL), and after stirring at room temperature for2 h, 1-(N-Boc)-4-piperidone (28 mmol) was subsequentlyadded, with the mixture heated at reflux for 24 h. Themixture was concentrated in vacuo and purified via columnchromatography to give 5. The Boc-protecting group wasremoved using trifluoroacetic acid in CH2Cl2 to provide 6.Finally, appropriate quinoline-4-carboxylic acid derivatives(1 mmol) was added to the mixture of 6 (1.1 mmol), HATU(1.2 mmol), and triethylamine (0.2 mL) in DMF (10 mL). Themixture was stirred at room temperature overnight, andthen added to ice water. The resulting precipitate wasfiltered, dried, and purified by column chromatography togive target compounds 7a~7m and 7q~7u.
  • 22
  • [ 10222-62-5 ]
  • (S)-2,7-dimethyl-3-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine trifluoroacetic acid salt [ No CAS ]
  • (S)-(2,7-dimethyl-3-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)(2-methoxyquinolin-4-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; 20 Example 1 : (S)-(2,7-dimethyl-3-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)(2-methylquinolin-5-yl)methanone General procedure: To a solution of (S)-2,7-dimethyl-3-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-4,5,6,7- tetrahydro-2H-pyrazolo[3,4-c]pyridine (Intermediate 13, 25 mg, 83.5 pmol) in CH2CI2 (2.0 mL) was added 2-methylquinoline-5-carboxylic acid (17.2 mg, 0.092 mmol), HATU (41.3 mg, 0.11 mmol), and N,N-diisopropylethylamine (43.2 pL, 0.25 mmol). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and purified by preparative HPLC (METHOD A) to afford the title compound as a white powder (13 mg, 33% yield). MS (ESI): mass calcd. for C24H23F3N6O, 468.2; m/z found, 469.0 [M+H]+. NMR (400 MHz, DMSO-d6) d 8.12 - 7.71(m, 3H), 7.66 - 7.29 (m, 2H), 7.10 (d, J= 16.6 Hz, 1H), 5.96 - 5.68 (m, 1H), 4.92 - 4.27 (m,1H), 3.89 - 3.59 (m, 6H), 2.74 - 2.58 (m, 4H), 2.31 - 2.13 (m, 2H), 1.67 - 1.30 (m, 3H).
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