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[ CAS No. 209960-29-2 ] {[proInfo.proName]}

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Product Details of [ 209960-29-2 ]

CAS No. :209960-29-2 MDL No. :MFCD09029885
Formula : C10H13FN2O Boiling Point : -
Linear Structure Formula :- InChI Key :VMIJMGVGJOUFCC-UHFFFAOYSA-N
M.W :196.22 Pubchem ID :11481003
Synonyms :

Calculated chemistry of [ 209960-29-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.53
TPSA : 38.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 1.24
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.72 mg/ml ; 0.00876 mol/l
Class : Soluble
Log S (Ali) : -1.59
Solubility : 4.99 mg/ml ; 0.0254 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.611 mg/ml ; 0.00311 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 209960-29-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 209960-29-2 ]

* 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 [ 209960-29-2 ]

[ 209960-29-2 ] Synthesis Path-Downstream   1~43

  • 2
  • [ 218301-62-3 ]
  • [ 209960-29-2 ]
YieldReaction ConditionsOperation in experiment
97% With 5%-palladium/activated carbon; hydrogen In ethanol for 18h; General procedure for the catalytic reduction of nitrobenzenes 8 and 12. General procedure: Palladium on carbon (5% w/w, 0.30 g) was added to a solution of the appropriate nitrobenzene (7.4 mmol) in ethanol (100 mL) and stirred under hydrogen (1 atm) for 18 h. The mixture was filtered through celite under an argon atmosphere, rinsing with ethanol. The filtrate was concentrated and dried in vacuo affording the crude aniline, which was used without purification.4-Morpholinoaniline 9 (from 8). lavender crystals yield 98%, mp 103.2-103.7 °C. 1H NMR (400 MHz, CDCl3) δ 2.97-3.06 (m, 4H), 3.44 (br s, 2H), 3.81-3.89 (m, 4H), 6.67 (d, J 8.6 Hz, 2H), 6.80 (d, J 9.0 Hz, 2H).2-Fluoro-4-morpholinoaniline (from 12). purple crystals, yield 97%. 1H NMR (400 MHz, CDCl3) δ 2.95-3.05 (m, 4H), 3.78-3.88 (m, 4H), 6.55 (d, J 8.6 Hz, 1H), 6.63 (dd, J 13.5, 2.2 Hz, 1H), 6.72 (t, J 9.4 Hz, 1H).
96% With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;
50% With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; Flow reactor;
8.4% With hydrogen In methanol for 2.5h;
With hydrogen In methanol for 2h; 224.B 1-(3-amidinophenyl)-3-methyl-5-[(3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl]pyrazole bis-trifluoroacetate Part B. Preparation of N-(3-fluoro-4-aminophenyl)morpholine. N-(3-fluoro-4-nitrophenyl)morpholine (6.01 g,26.59 mmol) and a catalytic amount of palladium on carbon(10%) were suspended in 100 mL methanol in a Parr flask. The reaction mixture was placed on the Parr Hydrogenator at 60psi for 2H. The reaction mixture was passed through a Celite pad and the filtrate was concentrated under reduced pressure to give 4.50 g of N-(3-fluoro-4-aminophenyl)morpholine an off-colored solid. 1H-NMR(DMSO-d6) δ: 6.73 (t,1H, J = 9.34), 6.28 (m,2H), 3.64 (bt, 4H, J = 4.58Hz), 2.76 (bt, 4H, J = 4.58Hz). ESI mass spectrum analysis m/z (relative intensity) 197 (M+H, 100). 19FNMR(DMSO-d6) δ: -124.455.
With hydrogen In methanol for 2.5h; 29 Preparation of 2-fluoro-4-morpholinoaniline 2-Fluoro-4-morpholinonitrobenzene (1.80 g) was dissolved in methanol (100 mL) and 10% Pd/C (94 mg) was added. The mixture was placed in a hydrogenator (45 psi) for 2.5 h. The reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated to give 1.51 g solid. 1H NMR (CDCl3) δ6.76-6.54 (m, 3H), 3.84 (t, 4H), 3.45 (bs, 2H), 3.02 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 197.1 (M+H, 100).
With hydrogen In methanol for 2.5h; 29 2-Fluoro-4-morpholinonitrobenzene (1.80 g) was dissolved in methanol (100 mL) and 10% Pd/C (94 mg) was added. The mixture was placed in a hydrogenator (45 psi) for 2.5 h. The reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated to give 1.51 g solid.1H NMR (CDCl3) δ 6.76-6.54 (m, 3H), 3.84 (t, 4H), 3.45 (bs, 2H), 3.02 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 197.1 (M+H, 100).
With palladium on activated charcoal; hydrogen In methanol
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 3h; 47.B Step B: Step B: 2-Fluoro-4-morpholine aniline To a solution of 4-(3-fluoro-4-nitrophenyl)morpholine (1.00g, 4.42mmol) in methanol (20mL) was added palladium carbon (517.41mg, 486.20μmol), and it was replaced three times with a hydrogen balloon and then stirred at room temperature for 3 hours. It was filtered with Celite and spin-dried to give the title compound. 1H NMR (400MHz, DMSO-d6) δ=6.73 - 6.63 (m, 2H), 6.54 (dd, J=1.9, 8.4 Hz, 1H), 4.58 (s, 2H), 3.74-3.65 (m, 4H), 2.97-2.85 (m, 4H).

Reference: [1]Fellowes, Thomas; Hong, Yuning; Lobachevsky, Pavel; Martin, Roger F.; Owyong, Tze Cin; Skene, Colin E.; White, Jonathan M. [Arkivoc, 2022, vol. 2022, # 4]
[2]Cantillo, David; Moghaddam, Mojtaba Mirhosseini; Kappe, C. Oliver [Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4530 - 4542]
[3]Örkényi, Róbert; Éles, János; Faigl, Ferenc; Vincze, Péter; Prechl, Anita; Szakács, Zoltán; Kóti, János; Greiner, István [Angewandte Chemie - International Edition, 2017, vol. 56, # 30, p. 8742 - 8745][Angew. Chem., 2017, vol. 129, # 30, p. 8868 - 8871,4]
[4]Quan, Mimi L.; Lam, Patrick Y. S.; Han, Qi; Pinto, Donald J. P.; He, Ming Y.; Li, Renhua; Ellis, Christopher D.; Clark, Charles G.; Teleha, Christopher A.; Sun, Jung-Hui; Alexander, Richard S.; Bai, Steve; Luettgen, Joseph M.; Knabb, Robert M.; Wong, Pancras C.; Wexler, Ruth R. [Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1729 - 1744]
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP946508, 2009, B1 Location in patent: Page/Page column 92
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US6339099, 2002, B1 Location in patent: Page column 105-106
[7]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP991638, 2005, B1 Location in patent: Page/Page column 46
[8]Location in patent: scheme or table Patil, Sudhakar G.; Bagul, Rahul R.; Swami, Mangesh S.; Kotharkar, Nandini; Darade, Kalpana [Chinese Chemical Letters, 2011, vol. 22, # 8, p. 883 - 886]
[9]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - EP3640247, 2020, A1 Location in patent: Paragraph 0293; 0295
  • 3
  • [ 209960-29-2 ]
  • 1-(3'-aminobenzisoxazol-5'-yl)-3-trifluoromethyl-5-[(2-fluoro-4-morpholinophenyl)aminocarbonyl]pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (dimethylamino)pyridine / CH2Cl2 / 12 h / 20 °C 2.1: acetoxyhydroxamic acid; potassium tert-butoxide / dimethylformamide / 12 h / 20 °C 2.2: HCl / ethanol / 80 °C
  • 4
  • [ 446-35-5 ]
  • [ 209960-29-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.81 g / tetrahydrofuran / 2 h / 20 °C 2: 8.4 percent / H2 / Pd/C / methanol / 2.5 h / 2327.17 Torr
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: palladium on activated charcoal; hydrogen / methanol
Multi-step reaction with 2 steps 1: ethanol / 0.17 h / 100 °C / 7500.75 Torr / Flow reactor 2: hydrogen; palladium 10% on activated carbon / ethanol / 50 °C / 760.05 Torr / Flow reactor
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 80 °C 1.2: 16 h / 20 °C 2.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 20 °C

YieldReaction ConditionsOperation in experiment
224.B 1-(3-amidinophenyl)-3-methyl-5-[(3-fluoro-4-(N-morpholino)phenyl) aminocarbonyl]pyrazole bis-trifluoroacetate Part B. Preparation of N-(3-fluoro-4-aminophenyl)morpholine. N-(3-fluoro-4-nitrophenyl)morpholine (6.01 g,26.59 mmol) and a catalytic amount of palladium on carbon(10%) were suspended in 100 mL methanol in a Parr flask. The reaction mixture was placed on the Parr Hydrogenator at 60 psi for 2 H. The reaction mixture was passed through a Celite pad and the filtrate was concentrated under reduced pressure to give 4.50 g of N-(3-fluoro-4-aminophenyl)morpholine an off-colored solid. 1 H-NMR(DMSO-d6) δ: 6.73 (t, 1 H, J=9.34), 6.28 (m, 2 H), 3.64 (bt, 4 H, J=4.58 Hz), 2.76 (bt, 4 H, J=4.58 Hz). ESI mass spectrum analysis m/z(relative intensity) 197 (M+H, 100). 19 FNMR(DMSO-d6) δ: -124.455.
  • 6
  • [ 110-91-8 ]
  • [ 367-24-8 ]
  • [ 209960-29-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate A 1-(3-amidinophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl)pyrazole bis-trifluoro acetate and 1-(3-Carboxamidophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl) pyrazole Part A. Preparation of 2-fluoro-4-(-N-morpholino)aniline. Morpholine(10.0 mL,115 mmol) was added to a mixture of 4-bromo-2-fluoroaniline(1.03 g,5.42 mmol), copper(I) bromide (0.039 g,0.27 mmol) and potassium carbonate(1.50 g,10.84 mmol). The reaction mixture was heated to 130° C. for 48 h, concentrated under reduced pressure and purified by flash chromotography to afford 0.11 g of pure 2-fluoro-4-(-N-morpholino)aniline. 1 H-NMR(DMSO-d6) δ: 6.73 (dd, 1 H, J1 =8.8 Hz, J2 =9.9 Hz), 6.64 (dd, 1 H, J1 =2.6 Hz, J2 =13.2 Hz), 6.57 (m, 1 H), 3.85 (m, 4 H), 3.02 (m, 4 H). ESI mass spectrum analysis m/z(relative intensity) 197 (M+H, 100). 19 FNMR (dmso-d6,300 MHz) δ: -133.
With potassium carbonate at 130℃; for 48h; 230.A; 231.A 1-(3-amidinophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phanyl)aminocarbonyl)pyrazole bis-trifluoro acetate and 1-(3-Carboxamidophonyl)-3-trifluoramethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl) pyrazole Part A. Preparation of 2-fluoro-4-(-N-morpholino)aniline. Morpholine(10.0 mL,115 mmol) was added to a mixture of 4-bromo-2-fluoroaniline(1.03 g, 5.42 mmol), copper(I) bromide (0.039 g,0.27 mmol) and potassium carbonate(1.50 g,1.0.84 mmol). The reaction mixture was heated to 130°C for 48h, concentrated under reduced pressure and purified by flash chromotography to afford 0.11 g of pure 2-fluoro-4-(-N-morpholino) aniline. 1H-NMR(DMSO-d6) δ: 6.73 (dd, 1H, J1 = 8.8Hz, J2 = 9.9Hz), 6.64 (dd, 1H, J1 = 2.6Hz, J2 = 13.2Hz), 6.57 (m,1H), 3.85 (m,4H), 3.02 (m,4H). ESI mass spectrum analysis m/z(relative intensity) 197 (M+H, 100). 19FNMR (dmso-d6,300MHz) δ: -133.
  • 7
  • [ 209960-29-2 ]
  • [ 754193-45-8 ]
  • [ 76-05-1 ]
  • [ 127-06-0 ]
  • [ 218299-35-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(3-fluoro-4-aminophenyl)morpholine; 2-(3-cyano-4-fluoro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride With dmap Stage #2: acetone oxime With sodium t-butanolate Stage #3: trifluoroacetic acid With hydrogenchloride more than 3 stages; 29 Preparation of 1-(3'-Aminobenzisoxazol-5'-yl)-3-trifluoromethyl-5-[(3-fluoro-4-morpholinophenyl)aminocarbonyl]pyrazole The title compound was prepared from 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-pyrazolecarboxylic acid and 2-fluoro-4-morpholinoaniline as a TFA salt by the same procedures described in Example 26. 1H NMR (DMSO-d6) δ9.39 (s, 1H), 8.06 (d, 1H), 7.77-7.48 (m, 4H), 6.81-6.75 (m, 2H), 3.77 (t, 4H), 3.15 (t, 4H) ppm. ESI mass spectrum z (rel. intensity) 491.2 (M+H, 100).
  • 8
  • [ 209960-29-2 ]
  • C13H9ClFN3O [ No CAS ]
  • [ 76-05-1 ]
  • [ 127-06-0 ]
  • [ 218299-50-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(3-fluoro-4-aminophenyl)morpholine; C13H9ClFN3O With dmap Stage #2: acetone oxime With sodium t-butanolate Stage #3: trifluoroacetic acid With hydrogenchloride more than 3 stages; 44 Example 44 1-(3'-Aminobenzisoxazol-5'-yl)-3-ethyl-5-[(2-fluoro-4-morpholinophenyl)aminocarbonyl]pyrazole The title compound was prepared in an analogous fashion as TFA salt. 1H NMR (acetone-d6) δ9.08 (s, 1H), 7.94 (d, 1H), 7.64 (m, 2H), 7.47 (d, 1H), 6.92 (s, 1H), 6.78 (m, 2H), 4.07 (bs, 2H), 3.77 (t, 4H), 3.1 (t, 4H), 2.70 (q, 2H), 1.28 (t, 3H) ppm. ESI mass spectrum z (rel. intensity) 451.2 (M+H, 100).
  • 9
  • [ 209960-29-2 ]
  • [ 209917-95-3 ]
  • [ 209960-25-8 ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 20℃; for 72h; 224.C 1-(3-amidinophenyl)-3-methyl-5-[(3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl]pyrazole bis-trifluoroacetate Part C. Preparation of 1-(3-cyanophenyl)-3-methyl-5-((3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl)pyrazole. Dimethylaminopyridine(0.28 g,2.25 mmol) was added to a solution of 1-(3-cyanophenyl)-3-methyl-pyrazole-5-carboxylic acid chloride (0.46 g,1.88 mmol) and N-(3-fluoro-4-aminophenyl)morpholine (0.37 g,1.88 mmol) in 20 mL methylene chloride. The reaction mixture was stirred at ambient temperature for 72H and then concentrated under reduced pressure. The resulting residue was purified via flash chromotography to give 0.070 g of pure 1-(3-cyanophenyl)-3-methyl-5-((3-fluoro-4-(N-morpholino)phenyl)aminocarbonyl)pyrazole. 1H-NMR(DMSO-d6) δ: 10.50 (s,1H) 7.93 (s,1H), 7.83 (d,1H, J = 7.33Hz), 7.73 (d, 1H, J = 8.79Hz), 7.62 (t, 1H, J = 7.87Hz), 7.53 (m,1H), 7.34 (d, 1H, J = 9.15Hz), 6.99 (t, 1H, J = 9.34Hz), 6.93 (s,1H), 3.69 (bt, 4H, J = 4.58Hz), 2.92 (bt, 4H, J = 4.58Hz), 2.28 (s,3H). ESI mass spectrum analysis m/z(relative intensity) 406 (M+H, 100), 833 (2M+Na). 19F NMR (dmso-d6,300MHz) δ: -122.081.
  • 10
  • [ 209960-29-2 ]
  • N-(3-cyanophenyl)-3-trifluoromethyl-pyrazole-5-carboxylic acid chloride [ No CAS ]
  • [ 209960-30-5 ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 20℃; for 20h; 230.B; 231.B 1-(3-amidinophenyl)-3-trifluoromethyl-5-((2-fluoro-4-(N-morpholino)phanyl)aminocarbonyl)pyrazole bis-trifluoro acetate and 1-(3-Carboxamidophonyl)-3-trifluoramethyl-5-((2-fluoro-4-(N-morpholino)phenyl)aminocarbonyl) pyrazole Part B. Preparation of 1-(3-cyanophenyl)-3-trifluoromethyl-5-((2'-fluoro-4'-(N-morpholino)phenyl)aminocarbonyl)pyrazole. 2-Fluoro-4-(N-morpholino)aniline(0.11 g,0.56 mmol) in 5 mL methylene chloride was dripped into a stirring solution of N-(3-cyanophenyl)-3-trifluoromethyl-pyrazole-5-carboxylic acid chloride(0.17 g,0.56 mmol) and dimethylaminopyridine (0.082 g, 0.67 mmol) in 10 mL methylene chloride. The reaction mixture was stirred at ambient temperature for 20h. The reaction mixture was concentrated under reduced pressure and purified by flash chromatography to give 0.19 g of pure 1-(3-cyanophenyl)-3-trifluoromethyl-5-[(2'-fluoro-4'-(N-morpholino)phenyl)aminocarbonyl]pyrazole. 1H-NMR(DMSO-d6)δ:7.94 (m, 1H), 7.86 (s,1H), 7.77 (m,3H), 7.61 (dd, 2H, J1 = 7.7Hz, J2 = 8.1Hz), 7.12 (s,1H), 3.85 (m,4H), 3.14 (m,4H).
  • 11
  • [ 209960-29-2 ]
  • [ 1313809-83-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 12
  • [ 209960-29-2 ]
  • [ 1313809-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 13
  • [ 209960-29-2 ]
  • [ 1313809-85-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 14
  • [ 209960-29-2 ]
  • [ 1313809-86-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 15
  • [ 209960-29-2 ]
  • [ 1313809-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 16
  • [ 209960-29-2 ]
  • [ 1313809-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 17
  • [ 209960-29-2 ]
  • [ 1313809-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 18
  • [ 209960-29-2 ]
  • [ 1313809-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 19
  • [ 209960-29-2 ]
  • [ 1313809-91-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 20
  • [ 209960-29-2 ]
  • [ 1313809-92-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 21
  • [ 209960-29-2 ]
  • [ 1313809-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 22
  • [ 209960-29-2 ]
  • [ 1313809-94-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 23
  • [ 209960-29-2 ]
  • [ 1313809-78-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C
  • 24
  • [ 209960-29-2 ]
  • [ 1313809-79-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 25
  • [ 209960-29-2 ]
  • [ 1313809-80-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 26
  • [ 209960-29-2 ]
  • [ 1313809-81-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 27
  • [ 209960-29-2 ]
  • [ 1313809-82-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 80 °C 2: 1-butyl-3-methylimidazolium hydroxide / 6 h / 20 °C 3: 1-butyl-3-methylimidazolium hydroxide / 3 h / 20 °C
  • 28
  • [ 209960-29-2 ]
  • [ 542-85-8 ]
  • [ 1357481-41-4 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 80℃;
  • 29
  • [ 110-91-8 ]
  • [ 446-35-5 ]
  • [ 209960-29-2 ]
  • 4-fluoro-2-(morpholin-4-yl)aniline [ No CAS ]
  • 2,4-bis(morpholin-4-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: morpholine; 2,4-Difluoronitrobenzene In ethanol at 100℃; for 0.166667h; Flow reactor; Stage #2: With palladium 10% on activated carbon; hydrogen; morpholine hydrofluoride at 50℃; Flow reactor;
  • 30
  • [ 209960-29-2 ]
  • 7-(1-phenylpyrazol-4-yl)-3-bromo-1-methylquinoxalin-2-one [ No CAS ]
  • C29H27FN6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 16h; Inert atmosphere; 47.C 7-(1-phenyl-1H-pyrazol-4-yl)-3-((2-fluoro-4-morpholinephenyl)amino)-1-methylquinoxaline-2(1H)-one Step C 7-(1-phenyl-1H-pyrazol-4-yl)-3-((2-fluoro-4-morpholinephenyl)amino)-1-methylquinoxaline-2(1H)-one Under a protection of nitrogen, to a solution of 7-(1-phenylpyrazol-4-yl)-3-bromo-1-methyl-quinoxalin-2-one (100.00mg, 253.00μmol) in dioxane (3mL) were added 2-fluoro-4-morpholine-aniline (99.29mg, 506.00μmol), cesium carbonate (247.30mg, 759.00μmol), Xantphos (14.64mg, 25.30μmol) and Pd(OAc)2 (11.36mg, 50.60μmol)), and it was stirred under nitrogen for 16 hours at 110°C. The reaction solution was cooled to room temperature, filtered through Celite and spin-dried to give a residue. The residue was separated by column to give the title compound. ES-ESI (m/z): 511 (M+H)+
  • 31
  • [ 209960-29-2 ]
  • 3-((2-fluoro-4-morpholinephenyl)amino)-1-methyl-7-(1H-pyrazol-4-yl)quinoxaline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate; oxygen / dimethyl sulfoxide / 16 h / 35 °C
  • 32
  • [ 209960-29-2 ]
  • [ 241809-79-0 ]
  • pyridin-3-ylmethyl 4-((2-fluoro-4-morpholinophenyl)carbamoyl)benzylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: 4-<N-(pyridin-3-ylmethylcarbonyl)aminomethyl>benzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃; for 3h; Stage #2: N-(3-fluoro-4-aminophenyl)morpholine With trifluoroacetic acid In tetrahydrofuran for 16h; 2.2.3. General Procedure for the Preparation of NsubstitutedBenzamide Derivatives General procedure: CDI (1.2 mmol) was added to a suspension of compound1 (1.0 mmol) in anhydrous THF (20 mL), and the mixturewas stirred for 3h at 60°C. After formation of the acyl imidazole,the clear solution was cooled down to room temperaturefollowed by the addition of different NH2-group containingintermediates (1.1 mmol) and trifluoroacetic acid (1.1mmol). The mixture was then stirred for 16 h. The reaction mixture was evaporated to remove THF, and the crude productwas stirred in a mixture of hexane and water (2:5, v/v)for 1 h. After filteration and desiccation, the solid obtainedwas triturated with dichloromethane twice to afford puretarget compounds 2 or MS-275. 2.2.4. Pyridin-3-ylmethyl 4-(2-aminophenylcarbamoyl) benzyl-carbamate (MS-275)Yield: 68%; mp: 157-159°C (lit.[12], mp:159-160°C;1H NMR (400 MHz, DMSO-d6, ppm): δ 9.62 (s, 1H, H-23),8.60 (s, 1H, H-1), 8.53 (d, J= 3.6 Hz, 1H, H-5), 7.92-7.98(m, 3H, H-24, H-11 and H-13), 7.79 (t, J= 8.0 Hz, 1H, H-3),7.36-7.43 (m, 3H, H-4, H-10 and H-14), 7.17 (d, J= 8.0 Hz,1H, H-17), 6.97 (t, J= 7.2 Hz, 1H, H-19), 6.78 (d, J= 7.0 Hz,1H, H-18), 6.60 (t, J= 7.2 Hz, 1H, H-20), 5.10 (s, 2H, H-6),4.88 (s, 2H, H-22), 4.28 (s, 2H, H-8); 13C NMR (100 MHz,DMSO-d6, ppm): δ 165.57 (C-15), 156.72 (C-7), 149.62 (C-1), 149.60 (C-5), 143.61 (C-9), 143.59 (C-21), 136.22 (C-3),133.69 (C-12), 133.14 (C-2), 128.31 (C-11, C-13), 127.22(C-10, C-14), 127.15 (C-17), 126.93 (C-16), 124.00 (C-4),123.80 (C-18), 116.73 (C-19), 116.59 (C-20), 63.73 (C-6),44.09 (C-8).
  • 33
  • [ 209960-29-2 ]
  • (R)-5-((1-(tert-butoxycarbonyl)piperidin-3-yl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • C27H34FN7O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 4.1.1. (R)-N-(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxyphenyl)-5-(piperid-in-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide trifluoroacetate (2) General procedure: A solution of (R)-5-((1-(tert-butoxycarbonyl)piperidin-3-yl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 35 (80 mg, 0.22 mmol), N1-(2-(dimethylamino)ethyl)-3-methoxy-N1-methylbenzene-1,4-diamine 41a (59mg, 0.27 mmol), EDCI (51 mg, 0.27 mmol), HOBT (34 mg, 0.25 mmol)and N,N-diisopropylethylamine (92 μL, 0.55 mmol) in DMF (5 mL) was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate (30 mL), washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (5%aqueous ammonia in MeOH/DCM 1: 20) to afford tert-butyl (R)-3-((3-((4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxyphenyl)carbamoyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)piperidine-1-carboxylate as a white solid (60 mg, 48%).To a solution of tert-butyl (R)-3-((3-((4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxyphenyl)carbamoyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)piperidine-1-carboxylatein dichloromethane (4 mL) was added trifluoroacetic acid (1 mL), and the mixture was stirred at room temperature for 2 h. The solvent was evaporated in vacuo and the residue was purified by triturating with methanol/diethyl ether (5 mL/1 mL) to give the title compound as a white solid (35 mg, 48%).
  • 34
  • [ 209960-29-2 ]
  • (R)-5-((1-(tert-butoxycarbonyl)piperidin-3-yl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • (R)-N-(2-fluoro-4-morpholinophenyl)-5-(piperidin-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: dichloromethane / 2 h / 20 °C
  • 35
  • [ 209960-29-2 ]
  • C26H32ClFN4O5 [ No CAS ]
  • C36H44F2N6O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
185 mg With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 160℃; for 0.833333h; Microwave irradiation; Inert atmosphere; 1.2 Step 2: A solution of compound X-1 (250 mg, 0.5 mmol), compound 1b (118 mg, 0.6 mmol), Pd2(dba)3 (45 mg, 0.05 mmol), Xantphos (54 mg, 0.1 mmol) and cesium carbonate (326 mg, 1 mmol) in 1,4-dioxane (15 mL) was reacted in microwave at 160° C. for 50 min under argon atmosphere. The reaction was followed by LC-MS until it was completed. The reaction solution was cooled to room temperature, diluted with EA, washed with water and saturated brine, the organic layer was dried, concentrated and purified by column chromatography to obtain 185 mg of compound X-2. MS m/z(ESI): 695.3 [M+H]+.
185 mg With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 160℃; for 0.833333h; Microwave irradiation; Inert atmosphere; 1.2 Step 2: A solution of compound X-1 (250 mg, 0.5 mmol), compound 1b (118 mg, 0.6 mmol), Pd2(dba)3 (45 mg, 0.05 mmol), Xantphos (54 mg, 0.1 mmol) and cesium carbonate (326 mg, 1 mmol) in 1,4-dioxane (15 mL) was reacted in microwave at 160° C. for 50 min under argon atmosphere. The reaction was followed by LC-MS until it was completed. The reaction solution was cooled to room temperature, diluted with EA, washed with water and saturated brine, the organic layer was dried, concentrated and purified by column chromatography to obtain 185 mg of compound X-2. MS m/z(ESI): 695.3 [M+H]+.
185 mg With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 160℃; for 0.833333h; Microwave irradiation; Inert atmosphere; 1.2 Step 2: Compound X-1 (250 mg, 0.5 mmol), Compound 1b (118 mg, 0.6 mmol), Pd 2(dba) 3 (45 mg, 0.05 mmol), Xantphos (54 mg, 0.1 mmol), Cesium Carbonate (326 mg, 1 mmol) ) solution in 1,4-dioxane (15 mL) was microwaved at 160 °C for 50 min under argon atmosphere. LC-MS was followed to complete the reaction. The reaction solution was cooled to room temperature, diluted with EA, washed with water and saturated brine respectively, the organic layer was dried, concentrated, and purified by column chromatography to obtain 185 mg of compound X-2.
  • 36
  • [ 209958-42-9 ]
  • [ 209960-29-2 ]
  • 37
  • C15H21FN2O3 [ No CAS ]
  • [ 209960-29-2 ]
YieldReaction ConditionsOperation in experiment
900 mg With hydrogenchloride In 1,4-dioxane; methanol at 20℃; Inert atmosphere; Step 2: Compound 1b-2 (1.38 g, 4.657 mmol), methanol (20 mL) and HCl/1,4-dioxane (4M, 10 mL) were added to a 100 mL flask. The mixture was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure to remove the solvent, the residue was washed with saturated sodium bicarbonate, extracted with dichloromethane, and the organic layer was dried and concentrated to obtain 900 mg of yellow solid compound 1b. MS m/z(ESI): 197.2[M+H]+.
900 mg With hydrogenchloride In 1,4-dioxane; methanol at 20℃; Inert atmosphere; Step 2: Compound 1b-2 (1.38 g, 4.657 mmol), methanol (20 mL) and HCl/1,4-dioxane (4M, 10 mL) were added to a 100 mL flask. The mixture was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure to remove the solvent, the residue was washed with saturated sodium bicarbonate, extracted with dichloromethane, and the organic layer was dried and concentrated to obtain 900 mg of yellow solid compound 1b. MS m/z(ESI): 197.2[M+H]+.
900 mg With hydrogenchloride In 1,4-dioxane; methanol at 20℃; 1.2 Step 2: Compound 1b-2 (1.38 g, 4.657 mmol), methanol (20 mL) and HCl/1,4-dioxane (4M, 10 mL) were added to a 100 mL flask, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure to remove the solvent, the residue was washed with saturated sodium bicarbonate, extracted with dichloromethane, and the organic layer was dried and concentrated to obtain 900 mg of compound 1b as a yellow solid.
  • 38
  • [ 209960-29-2 ]
  • (R)-6-((1-acryloylpiperidin-3-yl)amino)-7-fluoro-4-((2-fluoro-4-morpholinophenyl)amino)-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.83 h / 160 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 4: trifluoroacetic acid; triethylsilane / 2 h / 80 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.83 h / 160 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 4: trifluoroacetic acid; triethylsilane / 2 h / 80 °C
  • 39
  • [ 209960-29-2 ]
  • C31H36F2N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.83 h / 160 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.83 h / 160 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 40
  • [ 209960-29-2 ]
  • C34H38F2N6O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.83 h / 160 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.83 h / 160 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 41
  • [ 209960-29-2 ]
  • 4-{2-[2-(pyridin-2-yl)-1H-benzo[d]imidazol-6-yl]benzo[d]thiazol-6-yl}morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl acetamide / 20 °C / Inert atmosphere 2: Lawessons reagent / chlorobenzene / 3 h / Reflux
  • 42
  • [ 209960-29-2 ]
  • C23H19N5OSe [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl acetamide / 20 °C / Inert atmosphere 2: woollins’ reagent; pyridine / chlorobenzene / 48 h / 130 °C / Inert atmosphere; Sealed tube
  • 43
  • [ 209960-29-2 ]
  • 2-(pyridin-2-yl)benzimidazole-6-carbonyl chloride hydrochloride [ No CAS ]
  • N-(2-fluoro-4-morpholinophenyl)-2-(pyrid-2-yl)-1H-benzo[d]imidazole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% In N,N-dimethyl acetamide at 20℃; Inert atmosphere; General procedure for the preparation of amides 11O and 13O. General procedure: Acid chloride 10 (7.7 mmol, 1.05 equiv) was dissolved in anhydrous N,N-dimethylacetamide (40 mL) under nitrogen. To this was added a solution of the appropriate crude aniline (7.3 mmol) in a further 20 mL of anhydrous N,N-dimethylacetamide. The mixture was stirred at room temperature under nitrogen for 18 h, then diluted with water (100 mL), the pH adjusted to 8 using 0.8 M aqueous NaHCO3, and the resulting precipitate filtered off and dried in vacuo, affording the amide.N-(4-Morpholinophenyl)-2-(pyrid-2-yl)-1H-benzo[d]imidazole-6-carboxamide 11O (from aniline 9); brown-grey solid, yield 85%, mp 220 °C (dec). 1H NMR (400 MHz, DMSO-d6 + TFA-d) δ 2.96-3.16 (m, 4H), 3.63-3.82 (m, 4H), 6.94 (d, J 9.0 Hz, 2H), 7.50-7.59 (m, 1H), 7.60-7.78 (m, 3H), 7.89 (d, J 8.2 Hz, 1H), 8.02 (t, J 7.2 Hz, 1H), 8.29 (br s, 1H), 8.37 (d, J 7.8 Hz, 1H), 8.76 (d, J 3.9 Hz, 1H), 10.13 (s, 1H). 13C NMR (100 MHz, DMSO-d6 + TFA-d) δ 49.5, 66.5, 115.8, 122.0, 122.3, 123.1, 125.7, 130.2, 132.3, 138.2, 147.6, 148.2, 150.0, 152.9, 165.8. MS (ESI +ve) m/z 400.1807 (MH+) C23H22N5O2+ requires 400.1768 (Δ = 9 ppm). N-(2-Fluoro-4-morpholinophenyl)-2-(pyrid-2-yl)-1H-benzo[d]imidazole-6-carboxamide 13O (from 2-fluoro-4-morpholinoaniline); grey solid, yield 42%. 1H NMR (400 MHz, DMSO-d6 + TFA-d) δ 3.13 (br s, 4H), 3.73 (br s, 4H), 6.77 (d, J 8.6 Hz, 1H), 6.86 (d, J 13.3 Hz, 1H), 7.35 (t, J 8.8 Hz, 1H), 7.52-7.62 (m, 1H), 7.71 (d, J 8.2 Hz, 1H) 7.90 (d, J 8.2 Hz, 1H), 8.04 (t, J 7.4 Hz, 1H), 8.29 (br s, 1H), 8.37 (d, J 7.4 Hz, 1H), 8.77 (d, J 3.5 Hz, 1H), 9.91 (s, 1H). 13C NMR (100 MHz, DMSO-d6) + TFA-d) δ 48.6, 66.4, 102.7 (d, J 24 Hz), 110.6, 117.1, 117.2, 122.4, 123.2, 125.8, 128.6 (d, J 4 Hz), 129.3, 138.2, 148.0, 150.0, 150.75, 150.84, 152.8, 157.5 (d, J 244 Hz), 166.1. MS (ESI +ve) m/z 418.1676 (MH+) C23H21FN5O2+ requires 418.1674 (Δ = 0.5 ppm).
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