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[ CAS No. 1000802-75-4 ] {[proInfo.proName]}

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Chemical Structure| 1000802-75-4
Chemical Structure| 1000802-75-4
Structure of 1000802-75-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1000802-75-4 ]

CAS No. :1000802-75-4 MDL No. :MFCD07374993
Formula : C7H10BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FPYWLOGLINZGBB-UHFFFAOYSA-N
M.W : 166.97 Pubchem ID :2763121
Synonyms :

Calculated chemistry of [ 1000802-75-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.52
TPSA : 62.58 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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.46
Log Po/w (WLOGP) : -0.92
Log Po/w (MLOGP) : -0.84
Log Po/w (SILICOS-IT) : -0.78
Consensus Log Po/w : -0.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.4
Solubility : 6.6 mg/ml ; 0.0395 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 7.58 mg/ml ; 0.0454 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.42
Solubility : 6.3 mg/ml ; 0.0378 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 1000802-75-4 ]

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

Application In Synthesis of [ 1000802-75-4 ]

* 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 [ 1000802-75-4 ]

[ 1000802-75-4 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 1126423-11-7 ]
  • [ 1000802-75-4 ]
  • [ 1126423-13-9 ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; for 4h;Heating / reflux; Step 2:; 6B 6C; A 200 ml round-bottomed flask was charged with 6B (2.45 g, 7.14 mmol), 6-methyl-2- methoxypyridine-3-boronic acid (0.98 g, 5.87 mmol), [1,1 ' bis(diphenylphosphino) ferrocene] dichloropalladium(?) complex with dichloromethane (1 :1) (0.58 g, 0.71 mmol), and DME (50 mL). To the stirring solution, a solution of sodium carbonate (10 ml of 1.5 M, 15.0 mmol) was added via a syringe. The reaction mixture was maintained reflux for 4 hours before cooled to room temperature. After concentration, the resulting residue was taken up with ethyl acetate (200 mL), washed with water (3x100 mL), and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure and the resulting residue was purified using Combiflash chromatography on silica gel using 0-10 % ethyl acetate in hexanes as the solvent to provide the product 6C as a white solid (1.51 g, 76%). M.S. found for C2OH22N2O3: 339.2 (M+H)+.
  • 2
  • [ 1000802-75-4 ]
  • [ 1257834-21-1 ]
  • [ 1257834-24-4 ]
YieldReaction ConditionsOperation in experiment
25.8% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 18h; step 7-; A vial was charged with 158 (0.38 g, 977 mumol), 75 (326 mg, 1.95 mmol), Na2CO3 (311 mg, 2.93 mmol), Pd(PPh3)4 (0.113 g, 97.7 mumol) and DME. The reaction mixture was heated to 80 C. and stirred overnight. After 18 h, some 158 was still present. The reaction mixture was filtered through glass fiber paper and the filtrate was concentrated in vacuo. The crude material was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 50% EtOAc) to afford 0.120 g (25.8%) of 160.
  • 3
  • [ 1000802-75-4 ]
  • [ 1354455-95-0 ]
  • [ 1373516-68-7 ]
YieldReaction ConditionsOperation in experiment
53.8% With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 120℃; for 1h;Inert atmosphere; Sealed tube; Example 6N-{4-[2-tert-Butyl-4-(6-hydroxy-2-oxo-1,2-dihydro-pyridin-3-yl)-quinazolin-7-yl]-phenyl}-methanesulfonamide (I-6); 1step 1-A vial was charged with 36c (37 mg, 94.7 mumol, Eq), <strong>[1000802-75-4]2-methoxy-6-methylpyridin-3-ylboronic acid</strong> (19.0 mg, 114 mumol) and Cs2CO3 (92.5 mg, 284 mumol) dioxane (2 mL) and H2O (500 muA). The suspension was sparged with argon, the PdCl2(dppf) (3.46 mg, 4.73 mumol) was added, the vial sealed and heated thermally for 1 hr at 120 C. The mixture was partitioned between EtOAc and H2O and neutralized with 1N HCl. The organic extract was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC plate developed with 30% EtOAc/hexane to afford 24.3 mg (53.8%) of N-(4-(2-tert-butyl-4-chloropyrido[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (38).step 2-A sealable vial was charged with 38 (24.3 mg, 50.9 mumol), HBr (25.7 mg, 17.3 muL, 153 mumol) and HOAc (0.5 mL) flushed with argon, sealed and heated at 60 C. for 3 h. The mixture was cooled diluted with EtOAc and H2O and neutralized with satd. aq. NaHCO3 The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified on a preparative SiO2 TLC plate developed with 50% EtOAc/hexane to afford 20.4 mg of I-6.
  • 4
  • [ 1000802-75-4 ]
  • [ 1354455-88-1 ]
  • [ 1354455-89-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; for 1h;Inert atmosphere; Sealed tube; Heating; Example 1N-{4-[2-tert-Butyl-4-(6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-quinazolin-7-yl]-phenyl}-methanesulfonamide (I-1; SCHEME A)step 1: To a suspension of 20a (3 g, 14 mmol, CASRN 112253-70-0) in DCM cooled to 0 C. and maintained under a N2 atmosphere was added TEA and the suspension stirred for 15 min. To the suspension was added slowly pivaloyl chloride (1.68 g, 14 mmol) the solution was stirred over night RT. The solution was recooled to 0 C. and a second aliquot of pivaloyl chloride (300 muL) was added and the resulting mixture stirred for 2 h at 0 C. for 2 h then at RT for 2 h. The reaction mixture was concentrated in vacuo to afford 20b which was used without additional purification.step 2: To a suspension of 20b (4.2 g, 14 mmol) and EtOH (28 mL) was added aqueous NaOH (2.8 mL, 28 mmol, 10M solution) and the resulting mixture was heated at reflux under an N2 atmosphere for 1.5 h. The solution was cooled to RT, poured over ice and neutralized with1N HCl. The resulting mixture was twice extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated to afford 2.07 g of 22a as a yellow solid.step 3: A microwave vial was charged with 22a (0.5 g, 1.78 mmol), 4-methansulfonamido-phenyl boronic acid (0.421 g, 1.96 mmol, CASRN 380430-57-9), Pd(PPh3)4 (0.206 g, 0.178 mmol), Na2CO3 (0.566 g, 5.34 mmol), MeOH (3 mL) and toluene (1.5 mL). The vial was flushed with Ar for 5 min, sealed and irradiated in a microwave synthesizer at 115 C. The reaction mixture was cooled and concentrated. The insoluble material was triturated with Et2O which afford 0.55 g (84.3%) of 22b as a brown solid.step 4: To a suspension of 22b (0.1 g, 0.27 mmol) in benzene (0.5 mL) was added sequentially diethylaniline (73.0 muL, 0.45 mmol) and POCl3 (14.8 muL). The mixture was heated at reflux for 6 h, cooled and diluted with EtOAc. The resulting solution was washed sequentially with 1 N HCl, H2O, satd. aq. NaHCO3, H2O and brine. The solution was dried (MgSO4), filtered and evaporated to afford 24.step 5: A vial was charged with 24 (0.107 g, 0.274 mmol), 6-methyl-2-methoxy-pyridin-3-yl boronic acid (0.055 g, 0.33 mmol), PdC12(dPPf).CH2Cl2 (0.010 g, 0.014 mmol), Cs2CO3 (0.822 g, 0.268 mmol). dioxane (1 mL) and H2O (0.25 mL), purged with Ar for 10 min sealed and heated for 1 h. The solution was cooled to RT, diluted with EtOAc and sequentially extracted with twice with H2O and brine. The resulting solution was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 30% EtOAc) to afford 0.08 g of 26.step 6: A mixture of 26 (0.08 g, 0.169 mmol), 48% aq. HBr (52 muL) and HOAc was heated in sealed tube at 60 C. for 3 h. The tube was cooled and the mixture diluted with EtOAc, neutralized with satd. aq. NaHCO3 and stirred overnight at RT. The EtOAc had evaporated and the remaining yellow solid was filtered and washed with EtOAc and H2O. The solid was dried at 70 C. overnight in a vacuum oven which afforded I-1.
  • 5
  • [ 1000802-75-4 ]
  • [ 1454558-23-6 ]
  • [ 1454556-63-8 ]
  • [ 1454555-38-4 ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); triethylamine; at 85℃; for 2.25h; 5.6.22. Synthesis of Isopropyl 4-(3-(2-methoxy-6-methylpyridin-3-yl)pyrazolo[l,5-a]pyrimidin- 5-yl)piperazine-l-carboxylate To a 100 mL liter round bottom flask was added 2.00 g (5.43 mmol) of isopropyl 4-(3- bromopyrazolo[l,5-a]pyrimidin-5-yl)piperazine-l-carboxylate, 1.00 g (5.98 mmol) of (2-methoxy-6- methylpyridin-3-yl)boronic acid, 0.19 g (0.16 mmol) of Pd(PP i3)4, and a stirring rod. After adding all the solids, 30 ml of 2% TPGS-750-M solution was added, followed by the addition of 3.80 mL (27.15 mmol) triethylamine. The reaction flask was plunged into an oil bath preheated to 85C, and stirred vigorously. It took about 0.25 hr of stirring for all the suspended solids to dissolve completely. After stirring at 85C for about 2 hr, LCMS showed that the reaction was complete. It was allowed to cool to RT, dilute with 40 mL EtOAc. The organic layer was separated, and the aqueous layer was extracted twice with 30 mL portions EtOAc. The combined organic layers was washed with brine, dried over MgS04, and concentrated. A small volume of DCM was used to dissolve the crude mixture, and then loaded directly onto a 80 g silica gel column for separation on the ISCO. A gradient of 50% EtOAc/hex to 100% EtOAc was run for the first 15 minutes, and then the column was run with only EtOAc. The desired product begun eluting about 8 minutes into running with only EtOAc. The desbromo side product elutes together with the desired product. Even though the desbromo compound is spread through all the fractions containing the desired product, the percentage of the desbromo compound seem to decrease with time. Therefore, the first few tubes containing the highest percentages of the desbromo were discarded, and the remaining fractions were concentrated to obtain 1.73 g of about 84% purity at 254 nm (with about 16% desbromo compound). [Base on ^ nmr, the desbromo is over-estimated at the 254 nm on the UV, and under estimated on the UV at 220 nm]. The material was recrystallized twice using IPAC and heptanes, to afford 1.45 g (65% yield) of the desired product. *H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.30 (d, J=6.32 Hz, 6 H) 2.49 (s, 3 H) 3.59 - 3.68 (m, 4 H) 3.73 (dd, J=6.19, 3.66 Hz, 4 H) 4.07 (s, 3 H) 4.99 (dt, J=12.44, 6.28 Hz, 1 H) 6.36 (d, J=7.83 Hz, 1 H) 6.85 (d, J=7.58 Hz, 1 H) 8.35 (d, J=7.83 Hz, 1 H) 8.55 - 8.63 (m, 2 H); 13C NMR (101 MHz, CHLOROFORM-d) delta ppm 22.48, 24.10, 43.39, 44.94, 53.38, 69.37, 96.32, 101.34, 113.40, 116.03, 135.94, 136.12, 145.14, 146.15, 152.13, 155.35, 155.45, 159.49. LRMS (ESI) m/e 411 [(M + H)+, calcd for C21H26N6O3 410].
  • 6
  • [ 1000802-75-4 ]
  • N-[4-[(E)-2-(5-bromo-3-tert-butyl-2-methoxyphenyl)vinyl]phenyl]methanesulfonamide [ No CAS ]
  • N-[4-[(E)-2-[3-tert-butyl-2-methoxy-5-(2-methoxy-6-methyl-3-pyridyl)phenyl]vinyl]phenyl]methanesulfonamide [ No CAS ]
  • 7
  • [ 1000802-75-4 ]
  • [(S)-1-(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-pyrrolidin-3-yl]-methyl-carbamic acid isopropyl ester [ No CAS ]
  • (S)-isopropyl (1-(3-(2-methoxy-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.6 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,2-dimethoxyethane; water; at 140℃; for 0.5h;Microwave irradiation; To 80 mg (0.217 mmol) of (S)-isopropyl (1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-20 yl)(methyl)carbamate in a microwave vial was added, 54 mg (0.326 mmol) of <strong>[1000802-75-4](2-methoxy-6-methylpyridin-3-yl)boronic acid</strong>, 92 mg (0.435 mmol) of K3P04, 18 mg (0.022 mmol) PdCI2(dppf)2, 3ml of DME and then 1 ml water. The resulting mixture was microwaved at 140C for 0.5 hr. It wasdiluted with EtOAc, washed with brine, and the organic layer was dried over MgS04. It wasconcentrated and purified on the neutral PREP HPLC to obtain 50.6 mg of the desired product. 1H25 NMR (400 MHz, CHLOROFORM-d) 8 ppm 1.30 (d, J=6.32 Hz, 6 H) 2.13-2.31 (m, 2 H) 2.53 (s, 3 H)2.89 (s, 3 H) 3.43 (dd, J=10.61, 7.07 Hz, 1 H) 3.49-3.56 (m, 1 H) 3.70-3.76 (m, 2 H) 4.06 (s, 3 H)4.99 (m, 2 H) 6.61 (d, J=9.85 Hz, 1 H) 6.89 (d, J=7.83 Hz, 1 H) 7.79 (d, J=9.85 Hz, 1 H) 8.12 (s, 1 H)8.69 (d, J=7.83 Hz, 1 H). LRMS (ESI) mje 425 [(M +H)+, calcd for C22H2sN603 424].
  • 8
  • [ 1000802-75-4 ]
  • [ 1257830-36-6 ]
  • C28H31N3O4S [ No CAS ]
  • 9
  • [ 1000802-75-4 ]
  • 1-(2-[{(1H-pyrazol-3-yl)}oxymethyl]-3-methylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]
  • 1-(2-[1-(6-methyl-2-methoxypyridin-3-yl)-1H-pyrazol-3-yl]oxymethyl}-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.13 g With pyridine; copper diacetate; In acetonitrile; for 6h;Molecular sieve; Reflux; Production Example 5 (0486) A mixture of 0.5 g of 1-(2-[{(1H-pyrazol-3-yl)}oxymethyl]-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one mentioned in Reference Production Example 26, 0.35 g of <strong>[1000802-75-4]6-methyl-2-methoxypyridine-3-boronic acid</strong>, 0.48 g of copper(II) acetate, 0.75 g of Molecular Sieves 4A, 0.3 mL of pyridine, and 5 mL of acetonitrile was stirred with heating under reflux for 6 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.13 g of 1-(2-[1-(6-methyl-2-methoxypyridin-3-yl)-1H-pyrazol-3-yl]oxymethyl}-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 5). (0487) 1H-NMR (CDCl3) delta: 8.01 (1H, d, J=2.7 Hz), 7.90 (1H, d, J=7.7 Hz), 7.39-7.36 (2H, m), 7.27-7.23 (1H, m), 6.82 (1H, d, J=7.7 Hz), 5.77 (1H, d, J=2.7 Hz), 5.30 (2H, s), 4.01 (3H, s), 3.62 (3H, s), 2.54 (3H, s), 2.46 (3H, s).
0.13 g With pyridine; copper diacetate; In acetonitrile; for 6h;Molecular sieve; Reflux; The 0.5g of 1- (2 - [{(1H- pyrazol-3-yl) oxy} methyl] -3-methyl-phenyl) -4-methyl-1,4-dihydro-tetrazol - 5-one (referred to in the reference Preparation Example 26), 0.35g of 2-methoxy-6-methyl-pyridine-3-boronic acid, 0.48g of copper acetate (II), 0.75g of molecular sieve 4A, 0.3mL mixture of pyridine and 5mL of acetonitrile was heated under reflux for 6 hours with stirring. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.13g of 1- (2 - [1- (2-methoxy-6-methyl-pyridin-3-yl) lH-pyrazol-3 yl] oxy} methyl 3-methylphenyl) -4-methyl-1,4-dihydro-tetrazol-5-one (hereinafter referred to as the present compound 5).
  • 10
  • [ 1000802-75-4 ]
  • 4-(9-bromo-4-methoxy-3,3-dimethyl-2,3-dihydrofuro[3,2-g]quinolinyl)-3-methyl-N-phenylmethanesulfonamide [ No CAS ]
  • N-(4-(4-methoxy-9-(6-methyl-2-oxo-1,2-dihydropyridin-3-yl)-3,3-dimethyl-dihydrofuro[3,2-g]quinolin-6-yl)-3-methylphenyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
(9-bromo-4-methoxy-3,3-dimethyl-2,3-dihydrofuro [3,2-g] quinolinyl) prepared in Example 1, step 8, -3-methyl-N-phenylmethanesulfonamide (250 mg)<strong>[1000802-75-4]2-methoxy-6-methylpyridin-3-ylboronic acid</strong> (85.68 mg)Sodium carbonate (161.9 mg) andPd (PPh3) 4 (58.8 mg) was dissolved in methanol / toluene (2: 1)120 microwave 65min, concentrated with acetic acid dissolved, adding HBr, stirring at 60 for 1.5h after the reaction is complete, Concentrated to prepare the title compound as an off-white solid
  • 11
  • [ 1000802-75-4 ]
  • 4-(9-bromo-4-methoxy-3,3-dimethyl-2,3-dihydrofuro[3,2-g]quinolinyl)-N-phenylmethanesulfonamide [ No CAS ]
  • N-(4-(4-methoxy-3,3-dimethyl-9-(6-methyl-2-oxo-1,2-dihydropyridin-3-yl)-2,3-dihydrofuro[3,2-g]quinolin-6-yl)phenyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Prepared in Example 6, Step 14- (9-bromo-4-methoxy-3,3-dimethyl-2,3-dihydrofuro [3,2-g] quinolinyl) -N-phenylmethanesulfonamide (200 mg ),<strong>[1000802-75-4]2-methoxy-6-methylpyridine-3-boronic acid</strong>(84 mg), Sodium carbonate (132 mg) and Pd (PPh3) 4 (48.4 mg) were dissolved in methanol / toluene (2: 1), 120 C for 65 min, Concentrated with acetic acid dissolved, adding HBr, stirring at 60 for 1.5 h after the reaction is complete, concentrated,The title compound was isolated as an off-white solid
  • 12
  • [ 1000802-75-4 ]
  • 7-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • 7-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-5-(2-methoxy-6-methylpyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 100℃; for 16h; A stirred solution of 7-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine (Preparation 302 95, 150 mg, 0.345 mmol) in EtOH:water (4:1, 3 mL), <strong>[1000802-75-4](2-methoxy-6-methylpyridin-3-yl)boronic acid</strong> (86.32 mg, 0.517 mmol) and Na2CO3 (146.14 mg, 1.37 mmol) was degassed with Ar for 15 minutes and Pd(PPh3)4 (39.8 mg, 0.034 mmol) added and reaction mixture heated at 100 C. for 16 hours. The reaction was cooled to rt, diluted with water and extracted with EtOAc. The combined organics were dried (Na2SO4) and evaporated to dryness in vacuo. The residue was purified flash chromatography and prep-TLC to afford the 604 title compound as an off-white solid (26 mg, 15%). 1HNMR (400 MHz, DMSO-d6): 2.44 (s, 3H), 3.84 (s, 3H), 5.55 (s, 2H), 6.00 (br s, 2H), 6.92 (d, 1H), 7.36 (s, 1H), 7.42 (t, 1H), 7.51-7.61 (m, 3H), 7.82 (t, 1H), 8.16 (s, 1H), 8.61 (s, 1H). LCMS m/z=431 [MH]+
  • 13
  • [ 1000802-75-4 ]
  • 5-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-1,3,4-oxadiazin-2-one [ No CAS ]
  • 5-[4-(2-methoxy-6-methylpyridin-3-yl)-3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-1,3,4-oxadiazin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.0 mg With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); potassium carbonate; XPhos; In 1,4-dioxane; water; at 80℃; for 2h;Inert atmosphere; In a reaction vessel, 5-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-1,3,4- oxadiazin-2-one (150 mg, 538 muiotaetaomicronIota, Intermediate 64), (2-methoxy-6-methylpyridin-3- yl)boronic acid (135 mg, 808 muiotaetaomicronIota), potassium carbonate (149 mg, 1.08 mmol) and 2- (dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (15.4 mg, 32.3 muiotaetaomicronIota) were suspended in 2.4 mL 1,4-dioxane and 810 mu water. The mixture was degassed with nitrogen for 5 min. Then, chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1 '- biphenyl)[2-(2'-amino-1,1 '-biphenyl)]palladium(ll) (12.7 mg, 16.2 muiotaetaomicronIota) was added. Nitrogen was passed through the reaction mixture. It was stirred at 80 for 2 hours in a heating block. The mixture was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried using a water-resistant filter and the filtrate was concentrated under reduced pressure. The residue was dissolved in DMSO, filtered and purified by preparative HPLC, to give 87.0 mg (95 % purity, 42 % yield) of the title compound. LC-MS (Method 2): R, = 1.24 min; MS (ESIpos): m/z = 366 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 2.073 (2.23), 2.456 (14.29), 2.522 (0.48), 3.335 (16.00), 5.464 (12.60), 6.926 (2.62), 6.944 (2.85), 7.446 (2.39), 7.453 (2.89), 7.466 (2.72), 7.471 (2.82), 7.970 (1.51), 7.974 (1.61), 7.990 (1.37), 7.994 (1.51), 8.069 (3.06), 8.072 (2.92), 1 1.230 (4.14).
  • 14
  • [ 1000802-75-4 ]
  • (R)-5-bromo-1-isopropyl-N-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine [ No CAS ]
  • 1-isopropyl-5-(2-methoxy-6-methyl-3-pyridyl)-N-[(3R)-tetrahydrofuran-3-yl]pyrazolo[4,3-b]pyridin-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90℃; for 16h; A solution of 5-bromo-l,3-dimethyl-7-pyrrolidin-l-yl-pyrazolo[4,3-b]pyridine (40 mg, 0.14 mmol), 2-ethoxy-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (41 mg, 0.16 mmol), CS2CO3 (88 mg, 0.27) and Pd(dppf)CI2 (99 mg, 0.14 mmol) in dioxane (5 mL) and water (1 mL) was stirred at 90C for 16 hours. The reaction was concentrated .The residue was diluted with ethyl acetate (5 mL) and water (3 mL), filtered and extracted with ethyl acetate (5 mL x 3). The combined organic layers were washed with brine (5 mL x 2), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleur ethyl acetate = 10:1~1:1) followed by further purification by preparative HPLC to afford the title compound. 1H-NMR (400 MHz, Chloroform-d): delta 8.28 (d, J = 7.2 Hz, 1H), 8.17 (d, J = 5.2 Hz, 1H), 7.45 (s, 1H), 7.03 (dd, J = 7.2, 5.2 Hz, 1H), 4.46 (q, J = 7.2Hz, 2H), 4.13 (s, 3H), 3.37-3.35 (m, 4H), 2.64 (s, 3H), 2.05- 2.02 (m, 4H), 1.42 (t, 7 = 7.2 Hz, 3H). LC-MS: tR = 1.9 min (Method K), m/z = 338.1 [M+H]+.
  • 15
  • [ 1000802-75-4 ]
  • (S)-N-((S)-1-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-7-oxononyl)-6-ethyl-6-azaspiro[2.5]octane-1-carboxamide trifluoroacetate [ No CAS ]
  • C35H57N5O4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; water at 70℃; for 16h;
  • 16
  • [ 1000802-75-4 ]
  • C17H24IN5O3S [ No CAS ]
  • C24H32N6O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
77 mg With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 80℃; for 2.5h; 35-0 To a mixture PdCl2(dppf)-DCM complex (24.97 mg, 0.031 mmol), (2-methoxy-6-methylpyridin-3-yl)boronic acid (68.1 mg, 0.408 mmol), K3PO4 (130 mg, 0.611 mmol) was added a solution of Compound 35-3 (103 mg, 0.204 mmol) in dioxane (1.7 mL) and H2O (0.34 mL). The reaction was heated to 80° C. for 2.5 hours. The reaction mixture was diluted with DCM and extracted twice from water. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude mixture was purified by normal phase chromatography (12 g column) with a running gradient of 0-50% (2% MeOH/EtOAc)/DCM to afford 77 mg of Compound 35-4. LC-MS=501.5 [M-Boc+H]+.
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