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[ CAS No. 109486-01-3 ] {[proInfo.proName]}

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Product Details of [ 109486-01-3 ]

CAS No. :109486-01-3 MDL No. :MFCD09931332
Formula : C9H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XBUIBIHOIQNJQG-UHFFFAOYSA-N
M.W : 183.20 Pubchem ID :18702717
Synonyms :

Calculated chemistry of [ 109486-01-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.56
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.57
TPSA : 57.61 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) : -7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 0.33
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : 0.36
Log Po/w (SILICOS-IT) : 0.52
Consensus Log Po/w : 0.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -0.99
Solubility : 18.9 mg/ml ; 0.103 mol/l
Class : Very soluble
Log S (Ali) : -1.1
Solubility : 14.4 mg/ml ; 0.0788 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.14
Solubility : 132.0 mg/ml ; 0.719 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 109486-01-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 109486-01-3 ]

* 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 [ 109486-01-3 ]

[ 109486-01-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1126-09-6 ]
  • [ 109486-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: lithium hydroxide; water / methanol / 2 h / 20 °C
  • 2
  • 1-acryloylpiperidine-4-carboxylic acid [ No CAS ]
  • [ 345627-80-7 ]
  • 1-(1-acryloylpiperidine-4-carbonyl)-N-(5-(((5-(tert-butyl) oxazol-2-yl)methyl)thio)thiazol-2-yl)piperidine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40 mg 257] To a solution of l-acryloylpiperidine-4-carboxylic acid (50 mg, 0.27 mmol) in DMF (2.5 mL) was added triethylamine (0.11 mL, 0.81 mmol), EDCI (78 mg, 0.41 mmol) and HOBt (55 mg, 0.41 mmol) and the reaction was stirred at 0 C for 30 min. To the resulting solution was added <strong>[345627-80-7]N-(5-(((5-(tert-butyl)oxazol-2-yl)methyl)thio)thiazol-2-yl)piperidine-4-carboxamide</strong> (104 mg, 0.27 mmol) and the solution was stirred at room temperature for 3 h. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic solvents were dried over Na2S04. After removal of solvent, the residue was purified by silica gel column chromatography eluting with 0-4% methanol in DCM to afford the title compound (40 mg, yield 27%) as a white solid. 1H NMR (CDC13, 400MHz): delta 10.82 (br. S, 1H), 7.31 (s, 1H), 6.54-6.63 (m, 2H), 6.26 (d, J = 16.63 Hz, 1H), 5.69 (d, J = 10.76 Hz, 1H), 4.54-4.61 (m, 2H), 3.85-4.16 (m, 4H), 3.14-3.20 (m, 2H), 2.62-2.82 (m, 4H), 1.96-2.01 (m, 2H), 1.72-1.85 (m, 6H), 1.26 (s, 9H). LCMS: [M+H]+ = 546.15; Rt = 2.48 min
  • 3
  • [ 845907-79-1 ]
  • [ 109486-01-3 ]
YieldReaction ConditionsOperation in experiment
With water; lithium hydroxide In methanol at 20℃; for 2h; 12 l-Acryloylpiperidine-4-carboxylic acid To a solution of ethyl l-acryloylpiperidine-4-carboxylate (300 mg, 1.42 mmol) in MeOH: H20 (3: 3 mL) was added solution of lithium hydroxide (170 mg, 7.09 mmol) in water (2 mL) and stirred at room temperature for 2 h. The reaction mixture was acidified with IN HC1 and extracted with ethyl acetate (3 x 15 mL). The combined organic solvents were dried over Na2S04 and concentrated under vacuum to afford the title compound (200 mg, yield 77%) as an off white solid which was used directly in the next step without further purification. 1H NMR (CDCI3, 400MHz): δ 6.57 (dd, J = 10.52, 16.66 Hz, IH), 6.27 (d, J = 16.66 Hz, IH), 5.70 (d, J = 10.52 Hz, IH), 4.43-4.46 (m, IH), 3.93-3.97 (m, IH), 2.90-3.26 (m, 2H), 2.53-2.70 (m, IH), 1.96-2.00 (m, 2H), 1.61-1.79 (m, 2H). LCMS: [M+H]+ = 183.85; Rt = 2.32 min.
  • 4
  • [ 109486-01-3 ]
  • [ 2007172-26-9 ]
  • [ 2007170-92-3 ]
YieldReaction ConditionsOperation in experiment
18.69% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 1h; 16 Example-16: Synthesis of l-acryloyl-N-(3-(((8-ethyl-2-((l-methylpiperidin-4-yl)oxy)pyrazolo [l,5-a][l,3,5]triazin-4-yl)amino)methyl)phenyl)piperidine-4-carboxamide (Compound-88). Example-16: Synthesis of l-acryloyl-N-(3-(((8-ethyl-2-((l-methylpiperidin-4-yl)oxy)pyrazolo [l,5-a][l,3,5]triazin-4-yl)amino)methyl)phenyl)piperidine-4-carboxamide (Compound-88). HATU (0.15g, 0.39mmol) followed by DIPEA (0.15g, 1.16mmol) was added to a cooled solution of l-acryloylpiperidine-4-carboxylic acid (0.08g, 0.43mmol) in dry DMF (5mL) at 0 °C. N-(3-aminobenzyl)-8-ethyl-2-((l-methylpiperidin-4-yl)oxy)pyrazolo[l,5-a][l,3,5]triazin-4- amine (0.15g, 0.39mmol, intermediate-40) was added to above reaction mixture and the resulting reaction mixture was stirred for lh at room temperature. After completion of reaction, the reaction mixture was quenched with ice-water and diluted with ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate (2x50mL). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by prep. HPLC Column:XBRIDGE (19mm x 150mm), 0.01% HCOOH (A), Acetonitrile (B) to afford desired title compound (0.04g, 18.69%). 1HNMR (DMSO-+.
  • 5
  • [ 498-94-2 ]
  • [ 814-68-6 ]
  • [ 109486-01-3 ]
YieldReaction ConditionsOperation in experiment
86% With pyridine In N,N-dimethyl-formamide at 0 - 25℃; for 3h; Inert atmosphere; 1-Acryloylpiperidine-4-carboxylic acid (L1) Acryloyl chloride (3 mmol) and pyridine (266 μL, 3.3 mmol) were added into a solution of piperidine-4-carboxylic acid (3 mmol) in DMF (3 mL) at 0 °C, after the mixture was stirred at 25 °C for 3 h, the reaction mixture was partitioned between 50 mL EtOAc and 100 mL water. The EtOAc layer was washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using 5% MeOH in DCM 0.5% AcOH as eluent to afford L1 (473 mg, 86 %) as a white solid.
86% With pyridine In N,N-dimethyl-formamide at 0 - 25℃; for 3h; Inert atmosphere; 1-Acryloylpiperidine-4-carboxylic acid (L1) Acryloyl chloride (3 mmol) and pyridine (266 μL, 3.3 mmol) were added into a solution of piperidine-4-carboxylic acid (3 mmol) in DMF (3 mL) at 0 °C, after the mixture was stirred at 25 °C for 3 h, the reaction mixture was partitioned between 50 mL EtOAc and 100 mL water. The EtOAc layer was washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using 5% MeOH in DCM 0.5% AcOH as eluent to afford L1 (473 mg, 86 %) as a white solid.
32.14% Stage #1: piperidine-4-carboxylic acid With sodium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate at 0℃; for 0.166667h; Stage #2: prop-2-enoyl chloride In tetrahydrofuran; lithium hydroxide monohydrate at 0 - 20℃; for 1h; 8 Intermedia te-8 : Synthesis of l-acryloylpiperidine-4-carbox lic acid Intermedia te-8 : Synthesis of l-acryloylpiperidine-4-carbox lic acid. 2M NaOH (7.8mL, 15.5mmol) was added to a solution of piperidine-4-carboxylic acid (1.0 g, 7.81mmol) in (20mL) of THF:Water (6:4) at 0 °C and then stirred for lOmin. Added acryloyl chloride (0.7g, 7.69mmol) at 0 °C, then the reaction mixture was allowed to room temperature and stirred for lh. After completion of the reaction, the reaction mixture was quenched with ice water, adjusted pH to 4 by citric acid and extracted with ethyl acetate (2xl00mL). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated. The obtained product was triturated with diethyl ether, solid was filtered and dried to afford the title compound (0.45g, 32.14%). 1HNMR (DMSO-J6): δ 12.35 (s, IH), 6.82-6.73 (m, IH), 6.08-6.02 (dd, IH), 5.65-5.61 (dd, IH), 4.24-4.19 (d, IH), 3.96-3.91 (d, IH), 3.15-3.05 (t, IH), 2.82-2.74 (t, IH), 2.53-2.44 (m, IH), 1.84-1.79 (m, 2H), 1.43-1.35 (m, 2H); LCMS: m/z = 184 (M+H)+.
YieldReaction ConditionsOperation in experiment
With potassium hydroxide at 0℃; for 1h; Intermediate 17: tert-Butyl 4-(imidazo[1,2-a]pyrimidin-3-yl)-1 H-pyrrolo[2,3-b]pyridine- 1 -carboxylate General procedure: A solution of tert-butyl 4-(2-bromoacetyl)-1 H-pyrrolo[2,3-b]pyridine-1 -carboxylate (which can be prepared according to J. Med. Chem., 2008, 51(3), 487) (0.051 g, 0.15 mmol), 2- aminopyrimidine (0.018g, 0.188 mmol) and sodium bicarbonate (0.025g, 0.03 mmol) in isopropanol (1 ml_) was stirred and heated at 80°C for 2h. After cooling, the mixture was concentrated in vacuo and the residue was suspended in water and extracted with DCM. The organic phase was filtered through a phase separator and the filtrate was concentrated in vacuo. The residue was purified by FCC eluting with 0-4% methanol in DCM to give the title compound (0.017g) as a yellow gum. LCMS (Method 3) Rt 1.14 min m/z 280 (MH+-t-Bu]
  • 7
  • [ 1788861-30-2 ]
  • [ 109486-01-3 ]
  • [ 2600577-53-3 ]
YieldReaction ConditionsOperation in experiment
77% With 1-butyl-1,4-dihydropyridine-3-carboxamide In dimethyl sulfoxide at 20℃; for 1h; Irradiation; Inert atmosphere;
  • 8
  • [ 109486-01-3 ]
  • [ CAS Unavailable ]
  • [ 2763747-36-8 ]
YieldReaction ConditionsOperation in experiment
With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 5h; 21.6 Step 6: (R)-1-(4-(3-((8-(1H-Indol-3-yl)imidazo[1,2-b]pyridazin-6-yl)amino)piperidine- 1-Carbonyl)piperidin-1yl)prop-2-en-1-one preparation At 25°C, (R)-8-(1H-indol-3-yl)-N-(piperidin-3-yl)imidazo[1,2-b]pyridazin-6-amine (50.0 mg, 135.5 umol) and 1-acrylamidopiperidine-4-carboxylic acid (29.8 mg, 162.7 umol) were dissolved in DCM (1 mL), followed by the addition of DIPEA (35.0 mg, 271.1 umol) and T3P in 50% ethyl acetate ( 129.4 mg, 203.3 umol, 50% purity), the system was reacted at room temperature for 5 h. The reaction solution was concentrated in vacuo, separated and purified by high pressure preparation to obtain the compound of Example 21 (R)-1-(4-(3-((8-(1H-indol-3-yl)imidazo[1,2-b] Pyridazin-6-yl)amino)piperidin-1-carbonyl)piperidin-1 yl)prop-2-en-1-one.
  • 9
  • [ 109486-01-3 ]
  • [ 2250255-34-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
55% 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 N,N-dimethyl-formamide at 25℃; for 2h; 4.1.1. 1-Acryloyl-N-(4-(3-amino-6-methylisoxazolo[3,4-b]pyridin-4-yl)phenyl)piperidine-4-carboxamide (C1) Compound M5 (36 mg, 0.15 mmol) and side chain L1 (33 mg, 0.18 mmol) were added into a solution of HATU (152 mg, 0.79 mmol) in DMF(3 ml) followed by DIPEA (53 μL, 0.3 mmol) at 25 C. After the mixturewas reacted at 25 C for 2 h, the reaction mixture was partitioned between50 ml EtOAc and 25 × 4 ml water. The EtOAc layer was washedwith brine, dried over Na2SO4, filtered, concentrated and purified bycolumn chromatography on silica gel using 25 % ethyl acetate in petroleumether as eluent to afford C1 (33 mg, 55 %) as a yellow solid.
55% 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 N,N-dimethyl-formamide at 25℃; for 2h; 4.1.1. 1-Acryloyl-N-(4-(3-amino-6-methylisoxazolo[3,4-b]pyridin-4-yl)phenyl)piperidine-4-carboxamide (C1) Compound M5 (36 mg, 0.15 mmol) and side chain L1 (33 mg, 0.18 mmol) were added into a solution of HATU (152 mg, 0.79 mmol) in DMF(3 ml) followed by DIPEA (53 μL, 0.3 mmol) at 25 C. After the mixturewas reacted at 25 C for 2 h, the reaction mixture was partitioned between50 ml EtOAc and 25 × 4 ml water. The EtOAc layer was washedwith brine, dried over Na2SO4, filtered, concentrated and purified bycolumn chromatography on silica gel using 25 % ethyl acetate in petroleumether as eluent to afford C1 (33 mg, 55 %) as a yellow solid.
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