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Chemical Structure| 389621-84-5 Chemical Structure| 389621-84-5

Structure of 389621-84-5

Chemical Structure| 389621-84-5

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CAS No.: 389621-84-5

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Product Details of [ 389621-84-5 ]

CAS No. :389621-84-5
Formula : C11H14BNO4
M.W : 235.04
SMILES Code : O=C(C1=CC=C(B(O)O)C=C1)N2CCOCC2
MDL No. :MFCD03411952
InChI Key :KMNLIQJXZPBCDU-UHFFFAOYSA-N
Pubchem ID :2773546

Safety of [ 389621-84-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 389621-84-5 ]

* 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 [ 389621-84-5 ]

[ 389621-84-5 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 389621-84-5 ]
  • [ 866758-52-3 ]
  • (4-{4-[4-(chloro-difluoro-methoxy)-phenylamino]-phthalazin-1-yl}-phenyl)-morpholin-4-yl-methanone [ No CAS ]
  • 2
  • [ 389621-84-5 ]
  • [ 949557-71-5 ]
  • [ 949557-72-6 ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 70℃; for 1 - 18h; Step B: Preparation of N-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide: To a small round bottom flask was added N-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (30 mg, 0.0425 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (20.0 mg, 0.0849 mmol), and Pd(PPh3)4 (2.45 mg, 0.00212 mmol) and the mixture was dissolved in 3:1 DME:aqueous 2N Na2CO3 (2 mL). The mixture was stirred at 70 C. until the reaction was determined to be complete by LC/MS (1-18 hours). The reaction mixture was then partitioned between ethyl acetate (15 mL) and water (30 mL). The organic layer washed with brine, dried over Na2SO4 and evaporated to afford crude product. Purified by silica gel column chromatography (Biotage 12M) eluding with 1-5% MeOH/CHCl3 to give the desired product. Yield: 40.2 mg, 81%. LRMS (APCI pos) m/e 770.1 (M+H).
  • 3
  • [ 389621-84-5 ]
  • [ 949558-32-1 ]
  • [ 949558-33-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 1h; Step F: Preparation of 5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one: A suspension of 5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.013 g, 0.019 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.005 g, 0.02 mmol), Pd(PPh3)4 (0.001 g, 0.0009 mmol) and lithium chloride (0.003 g, 0.08 mmol) in dioxane (0.5 mL) and 2 M aqueous Na2CO3 (0.5 mL) was stirred at 100 C. for 1 hour. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to yield 0.014 g crude product as a yellow gum. The crude material was used without further purification in the following step. LRMS (APCI pos) m/e 738 (M+1).
  • 4
  • [ 389621-84-5 ]
  • [ 949556-71-2 ]
  • [ 949558-41-2 ]
YieldReaction ConditionsOperation in experiment
12% Step C: Preparation of (4-(4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)phenyl)(morpholino)methanone: A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.30 g, 0.612 mmol; prepared as in Example 7, Step B), Cs2CO3 (0.299 g, 0.918 mmol), and <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.151 g, 0.643 mmol) in DME (3 mL) was degassed under nitrogen for 10 minutes and tetrakistriphenylphosphinepalladium (0.035 g, 0.03 mmol) was added. The reaction mixture was heated at 85 C. for 15 hours. The precipitate was removed by filtration with a mixture of EtOAc and MeOH. The filtrate was concentrated and the crude material was purified by silica gel flash column chromatography (1% MeOH in CH2Cl2) to afford 39 mg (12%) of the desired product. LRMS (APCI pos) m/e 554.1 (M+1).
  • 5
  • [ 389621-84-5 ]
  • [ 949558-52-5 ]
  • [ 949558-53-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 20 - 100℃; Step E: Preparation of 2-(cyclohexylmethyl)-5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one: A suspension of 2-(cyclohexylmethyl)-5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one (0.025 g, 0.037 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.010 g, 0.044 mmol), Pd(PPh3)4 (0.002 g, 0.002 mmol) and lithium chloride (0.006 g, 0.147 mmol) in dioxane (1 mL) and 2 M aqueous Na2CO3 (1 mL) was stirred at 100 C. for 35 minutes and then at room temperature overnight. The reaction mixture was partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1*). The combined organic layers were dried over Na2SO4, filtered and concentrated to yield 0.027 g crude product as a yellow gum. The crude material was used without further purification in the following step. LRMS (APCI pos) m/e 743 (M+1).
  • 6
  • [ 389621-84-5 ]
  • [ 344940-69-8 ]
  • 4-{3-amino-6-[4-(morpholin-4-ylcarbonyl)phenyl]pyrazin-2-yl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Microwave; 4-(2-amino-5-bromopyrazin-3-yl)phenol (15 mg, 0.06 mmol), [4-(Morpholine-4- carbonyl)phenyl]boronic acid (20.2 mg, 0.086 mmol), tetrakis(triphenylphosphine)palladium (4 mg, 0.0034 mmol) and Na2COa (aq) (0.2 ml, 0.2 mmol) were suspended in DME (1 ml) and heated in the microwave to 1200C for 15 minutes. The mixture was evaporated and dissolved in MeOH ( 1 ml) and purified by reversed phase preparative HPLC using XTerra Prep MS C 18 5mum 19 x 50 mm, flow 25 ml/min, 50 mM pH IO NH4HCO3 / ACN, fractions collected based on UV-signal (254 nm). Yield: 3.2 mg (15%). Light yellow solid. MS (electronspray) M+H+ m/z 377.1.
  • 7
  • [ 389621-84-5 ]
  • [ 1000068-47-2 ]
  • 4-{6-[4-(morpholin-4-ylcarbonyl)phenyl]pyrazin-2-yl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130℃; for 0.166667h;Microwave; 4-(6-chloropyrazin-2-yl)phenol (200 mg, 0.97 mmol), 4-(Morpholine-4- carbonyl)phenyl]boronic acid, (300 mg, 1.27 mmol), tetrakis(triphenylphosphine)palladium (20 mg, 0.017), NaHCO3 (200 mg, 2.38 mmol) and water (1 ml) were suspended in DME (3 ml) and heated to 1300C for 10 minutes in the microwave. The mixture was diluted with dichloro- methane, filtered and transferred to a separation funnel. The organic phase was washed with water (Ix), brine (Ix), dried (MgSC^) and evaporated. The crude product was purified by suspending it with dichloromethane (sparingly soluble) and filtered. The grey powder was washed with dichloromethane (2x) and dried in vacuo. Yield 1 18 mg (33%). Grey solid. HPLC 96% Rt= I .74 (system A. 10-97% MeCN over 3 minutes). HPLC 95% Rt=I .62 (system B. 10-97% MeCN over 3 minutes). MS (electronspray; [M+H]+) m/z 362.4.IH NMR (400 MHz, DMSO-D6) delta ppm 3.49 - 3.75 (m, 6 H) 6.93 (d, J=8.78 Hz, 2 H) 7.58 (d, J=8.28 Hz, 2 H) 8.13 (d, J=8.78 Hz, 2 H) 8.30 (d, J=8.53 Hz, 2 H) 9.13 (s, 2 H) 9.95 (s, 1 H).
  • 8
  • [ 389621-84-5 ]
  • [ 850727-85-4 ]
  • 4-[(aminocarbonyl)amino]-1-[4-(morpholin-4-yl-carbonyl)phenyl]-1H-pyrazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper diacetate; In dichloromethane; [00714] Example 9: 4- [ (aminocarbonyl) amino]-l- [4- (morpholin-4-yl- carbonyl) phenyl]-1 H-pyrazole-3-carboxamide; [00716] A suspension of 4-[(aminocarbonyl) amino]-1 H-pyrazole-3- carboxamide (150 mg, 0.89 mmol) (prepared according to Example 19, from 4- amino-1 H-pyrazole-3-carboxamide, see J. Am. Chem. Soc. 78, 2418-2422 (1956) ) in pyridine (2.0 mL) and CH2CI2 (1. 0 mL) was treated with 4- (morpholine- 4-carbonyl) phenylboronic acid (208 mg, 0.89 mmol) and Cu (OAc) 2 (161 mg, 0.89 mmol). The reaction was stirred under nitrogen overnight. The crude mixture was concentrated, and redissolved in DMF (2 mL). The reaction mixture was then filtered through a syringe filter (0. 45 um), purified by prep. rpHPLC, and lyophilized to give the title compound as a white solid. ESI mass spectrum for C16H19N6O4+: 359.18 (M+1).
  • 10
  • [ 389621-84-5 ]
  • [ 874347-40-7 ]
  • C35H47N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In ethanol; at 120℃; for 0.333333h;Microwave; A tube containing 82 (30 mg), 4-(4-morpholinocarbonyl)phenylboronic acid (263 mg), Pd(Ph3P)2Cl2 (2 mg) and NEt3 (31 muL) in EtOH (900 muL) was sealed and heated in the microwave at 120 C. during 20 mins. The reaction mixture was added to silica gel (1 g) and the solvent allowed to evaporate; purification of the residue by silica gel chromatography (50->100% EtOAc/hexanes) gave 109 as a clear colorless oil, 14 mg. MS (ESI(+)) m/e 606.4 (M+H)+.
  • 11
  • [ 389621-84-5 ]
  • [ 918643-41-1 ]
  • (4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)(morpholino)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 85℃; for 18h; Example 130; N-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide; Step A: Preparation of (4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)(morpholino)methanone; A sealable tube was charged with 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)aniline (Example 6, Step A, 0.200 g, 0.518 mmol), cesium carbonate (0.253 g, 0.777 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.183 g, 0.777 mmol) and DME (2 mL). The mixture was degassed under nitrogen for 10 minutes and Pd(PPh3)4 (0.0299 g, 0.0259 mmol) was added as a solid. The mixture was heated to 85 C. for 18 hours. The crude was diluted with water (300 mL), extracted with EtOAc/MeOH (4:1, 2×300 mL), dried organic over sodium sulfate, filtered and concentrated. The crude product was purified by preparative TLC (2.0 mm thickness) eluting with EtOAc/MeOH (9:1) to give product (31 mg, 12%) as a white solid. LRMS (APCI+) 450 m/z (M+1) detected.
  • 12
  • [ 389621-84-5 ]
  • [ 946505-31-3 ]
  • 5-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 0.5h; Example 144; 5-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one; A suspension of 5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (Example 143, Step F, 0.018 g, 0.0316 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.009 g, 0.038 mmol), Pd(PPh3)4 (0.002 g, 0.002 mmol) and lithium chloride (0.005 g, 0.126 mmol) in dioxane (1 mL) and 2 M aqueous Na2CO3 (1 mL) was stirred at 100 C. for 30 minutes. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 10:1 CH2Cl2/MeOH. The product was obtained (12.9 mg; 65%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 9.04 (br s, 1H), 8.55 (d, 1H), 8.17 (s, 1H), 8.12 (s, 1H), 7.99 (m, 2H), 7.89 (dd, 1H), 7.69 (m, 1H), 7.58-7.49 (m, 5H), 7.38 (m, 2H), 7.17 (m, 1H), 6.70 (dd, 1H), 3.63 (m, 8H), 3.59 (s, 3H). LRMS (APCI pos) m/e 634 (M+1).
  • 13
  • [ 389621-84-5 ]
  • [ 946505-55-1 ]
  • 5-(2,5-difluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 0.5h; Step D: Preparation of 5-(2,5-difluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one; A suspension of 5-(2,5-difluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.0105 g, 0.0178 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.005 g, 0.021 mmol), Pd(PPh3)4 (0.001 g, 0.001 mmol) and lithium chloride (0.003 g, 0.071 mmol) in dioxane (0.5 mL) and 2M aqueous Na2CO3 (0.5 mL) was stirred at 100 C. for 30 minutes. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (4.5 mg; 39%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.54 (br s, 1H), 7.96 (s, 1H), 7.84-7.77 (m, 3H), 7.57-7.46 (m, 5H), 7.42 (t, 2H), 7.24 (m, 1H), 7.08 (m, 1H), 6.71-6.62 (m, 2H), 3.99-3.40 (m, 8H), 3.68 (s, 3H). LRMS (APCI pos) m/e 652 (M+1).
  • 14
  • [ 389621-84-5 ]
  • [ 946505-59-5 ]
  • 2-(benzylamino)-5-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 0.5h; Step E: Preparation of 2-(benzylamino)-5-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one; A suspension of 2-(benzylamino)-5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one (0.0157 g, 0.0269 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.008 g, 0.032 mmol), Pd(PPh3)4 (0.002 g, 0.002 mmol) and lithium chloride (0.005 g, 0.107 mmol) in dioxane (0.5 mL) and 2M aqueous Na2CO3 (0.5 mL) was stirred at 100 C. for 30 minutes. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (11.4 mg; 66%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.50 (d, 1H), 7.99 (s, 1H), 7.84-7.78 (m, 3H), 7.66 (dd, 1H), 7.55-7.45 (m 3H), 7.43-7.32 (m, 5H), 7.32-7.24 (m, 2H), 658 (d, 1H), 4.72 (d, 2H), 3.96-3.60 (m, 8H), 3.50 (s, 3H). LRMS (APCI pos) m/e 648 (M+1).
  • 15
  • [ 389621-84-5 ]
  • [ 946505-64-2 ]
  • 6-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 0.833333h; Step H: Preparation of 6-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one; A suspension of 6-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (0.035 g, 0.060 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.017 g, 0.0721 mmol), Pd(PPh3)4 (0.003 g, 0.003 mmol) and lithium chloride (0.010 g, 0.240 mmol) in dioxane (1 mL) and 2M aqueous Na2CO3 (1 mL) was stirred at 100 C. for 50 minutes. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (23 mg; 59%) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) 8.51 (d, 1H), 8.01 (s, 1H), 7.85-7.79 (m, 3H), 7.73-7.65 (m, 3H), 7.55-7.49 (m, 3H), 7.46 (m, 2H), 7.30 (m, 1H), 7.22, (m, 1H), 6.59 (dd, 1H), 4.33 (m, 4H), 3.95-3.36 (m, 8H). LRMS (APCI pos) m/e 646 (M+1).
  • 16
  • [ 389621-84-5 ]
  • [ 845889-22-7 ]
  • C27H35N5O6S [ No CAS ]
  • 17
  • [ 389621-84-5 ]
  • [ 960409-09-0 ]
  • [ 960409-44-3 ]
YieldReaction ConditionsOperation in experiment
65% With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; for 4h;Reflux; Inert atmosphere; Ethyl 3-[3-(3-methoxypropoxy)-4-[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate (0.8 g, 1.9 mmol) was dissolved in dimethoxyethane (12 mL) and ethanol (1.2 mL). 4-Morpholine-4-carbonylphenylboronic acid (0.50 g, 2.1 mmol) was added and argon: was bubbled in the mixture for 15 minutes. Cesium fluoride (0.6 g, 4.2 mmol) and tetrakistriphenylphosphine palladium (0.11 g, 0.1 mmol) were added and the mixture was brought to reflux under an argon atmosphere for 4 hours. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in ethyl acetate/water (15 mL/15 mL). The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 7/3) to yield 0.57 g (65%) of the desired product as a yellow oil.
  • 18
  • [ 389621-84-5 ]
  • (cis)-2-bromo-5-methyl-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid [ No CAS ]
  • (cis)-5-methyl-2-(4-(morpholine-4-carbonyl)phenyl)-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium phosphate; In N,N-dimethyl-formamide; at 110℃; for 0.833333h;Inert atmosphere; EXAMPLE 21; Step 1 : (/C)-5-methyl-2-(4-(morpholine-4-carbonyl)phenyl)-4-phenyl-5,6-dihydro- 4H-cyclopenta[b]thiophene-5-carboxylic acid[00241] A solution of the acid of Preparation 2, (cis)-2-bromo-5-methyl-4-phenyl- 5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid (80 mg, 0.237 mmol), 4- (morpholine-4-carbonyl)phenylboronic acid (112 mg, 0.474 mmol) and 2M potassium phosphate (0.593 ml, 1.186 mmol) in DMF (2 ml) was degassed with nitrogen for 15 min. To this solution was added tetrakis (triphenyl phosphine)palladium(O) (27.4 mg, 0.024 mmol). The reaction mixture was degassed for additional 5 min, then sealed and heated in a heating block (OptiChem Digital Hotplate Stirrer) at 110 0C for 50 min. The reaction mixture was cooled, filtered, and was taken into ethyl acetate and water. The organic phase was washed (brine), dried (MgSO4) and concentrated <n="73"/>to give the crude (177 mg), which was purified via flash silica gel column eluting with 0-1% MeOH in CHCl3 to give (c)-5-methyl-2-(4-(morpholine-4- carbonyl)phenyl)-4-phenyl-5,6-dihydro-4H-cyclopenta[b] thiophene-5-carboxylic acid as a white solid, (86 mg, 81% yield). IH NMR (500 MHz, MeOD) delta ppm 7.64 (2 H, d, J=8.25 Hz), 7.40 (2 H, d, J=8.25 Hz), 7.20 (2 H, t, J=7.15 Hz), 7.15 (1 H, d, J=7.15 Hz), 7.05 (3 H, m), 4.12 (1 H, s), 3.83 (1 H, d, J=15.95 Hz), 3.72 (4 H, m), 3.63 (2 H, m), 3.49 (2 H, m), 2.78 (1 H, d, J=15.95 Hz), 1.64 (3 H, s). LCMS (m/z) 448.1; HPLC Rt: 3.361 min (Method A).
  • 19
  • [ 389621-84-5 ]
  • cis-2-bromo-4-(3-fluorophenyl)-5-methyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid [ No CAS ]
  • cis-4-(3-fluorophenyl)-5-methyl-2-(4-(morpholine-4-carbonyl)phenyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With dipotassium hydrogenphosphate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 113℃; for 0.5h;Inert atmosphere; Step 6: (/C)-4-(3-fluorophenyl)-5-methyl-2-(4-(morpholine-4-carbonyl)phenyl)-5,6- dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid; [00249] A solution of the product of Step 5 (90 mg, 0.253 mmol) and 2M potassium phosphate, dibasic (0.633 ml, 1.267 mmol) in DMF (2 ml) was purged with nitrogen for 10 minutes. To this solution was added tetrakis (triphenyl phosphine)palladium(O) (29.3 mg, 0.025 mmol). After purging with nitrogen for an additional 10 minutes, the reaction solution was heated at 113 0C for 0.5 hour. The product mixture was taken into ethyl ether and water. The organic phase was washed with sat'd NaHCtheta3. The combined aqueous phase was adjusted to acidic with cone. HCl, and was extracted with ethyl acetate. The organic phase was washed (brine), dried (MgSO4) and concentrated to give the crude product which was purified via flash chromatography (12 g silica gel cartridge with eluents of 0-40% ethyl acetate in hexane to afford (cis)-4-(3-fluorophenyl)-5-methyl-2-(4-(morpholine-4- carbonyl)phenyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylic acid as a white solid (75 mg, 64%). IH NMR (400 MHz, MeOD) delta ppm 7.65 (2 H, d, J=8.53 Hz), 7.41 (2 H, d, J=8.53 Hz), 7.17 - 7.26 (1 H, m), 7.06 (1 H, s), 6.86 - 6.93 (2 H, m), 6.74 - 6.79 (1 H, m), 4.14 (1 H, s), 3.82 (1 H, d, J=16.56 Hz), 3.67 (4 H, br m), <n="78"/>3.50 (2 H, br m), 2.79 (1 H, d, J=16.31 Hz), 1.64 (3 H, s); ); LCMS m/z 466.1[M+1];HPLC: Rt 3.853 min. (Method A)
  • 20
  • [ 389621-84-5 ]
  • [ 28033-01-4 ]
  • [ 1235467-68-1 ]
YieldReaction ConditionsOperation in experiment
33% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; toluene; at 110℃; for 64h;Inert atmosphere; A mixture of methyl 3-amino-2,6-dibromoisonicotinate (11.4 g, 36.6 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (8.7 g, 33.3 mmol), and powdered sodium carbonate (8.12 g, 77 mmol) in a mixture of toluene (90 mL) and methanol (30 mL) was degassed and then backfilled with nitrogen twice.Tetrakis(triphenylphosphine)-palladium(0) (1.93 g, 1.67 mmol) was added and the reaction was degassed and backfilled with nitrogen. After stirred in a 110 C oil bath for 64 hr, the reaction was cooled and then partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic phase was separated and washed with saturated aqueous sodium bicarbonate, brine, and then dried over sodium sulfate and the solvents removed. The residue was suspended in EtOAc and the solid was collected by filtration and washed with EtOAc to give methyl 3-amino-6-bromo-2-(4- (morpholine-4-carbonyl)phenyl)-isonicotinate (3.29 gm, 24 %). Flash silica gel chromatography of the filtrate (step gradient elution with hexane containing 10 to 20 % EtOAc and then methylene chloride containing 1 to 4 % MeOH) gave additional 4.63g (33%) of pure product and 2.2 g of material that contained 65% of the product according to LC/MS. MS (ESI) m/z 418 and 420 (M-H). 1H NMR (CDCl3) delta ppm 7.83 (1 H, s), 7.68 (2 H, d, J=8.24 Hz), 7.52 (2 H, d, J=7.93 Hz), 5.93 (2 H, br. s.), 3.92 (3 H, s), 3.78 (4 H, br. s.), 3.62 (2 H, br. s.), 3.46 (2 H, br. s.).
  • 21
  • [ 79271-22-0 ]
  • [ 389621-84-5 ]
YieldReaction ConditionsOperation in experiment
Isopropylmagnesium chloride (27.8 mL, 2 M in THF, 55.6 mmol) was added to a solution of bis(2-dimethylaminoethyl) ether (10.5 mL, 55.6 mmol) in THF (230 mL) 15 C. After 20 minutes, (4-iodophenyl)-(morpholino)methanone (14.7 g, 46.4 mmol) was added and the reaction was removed from the cooling bath. After 1 hr, another 0.8 eq of isopropylmagnesium chloride was added. Trimethyl borate (10.6, 93 mmol) was added after 15 minutes, and after stirring 40 min, the reaction was quenched with 150 ml 1 N aqueous HCl. After stirring at room temperature for 2 hr, THF was removed on the rotary evaporator and the residue was extracted three times with EtOAc. The organic extracts were dried with Na2SO4. The solvent was removed and the residue was twice suspended in toluene and the solvent removed on the rotary evaporator. The resulting white solid was suspended in hexane and this was heated at reflux for 5 minutes. After cooling to room temperature, the white solid was collected by filtration and air-dried to afford 4-(morpholine-4- carbonyl)phenylboronic acid (8.7 g). MS (ESI) m/z 236.1 (M+H). 1H NMR (MeOD) delta ppm 7.78 (2 H, d, J=7.30 Hz), 7.36 (2 H, d, J=8.06 Hz), 3.72 - 3.41 (8 H, m).
  • 22
  • [ 389621-84-5 ]
  • [ 1198277-84-7 ]
  • [ 1198278-00-0 ]
  • 23
  • [ 389621-84-5 ]
  • 8-bromo-5-methyl-[1,2,4]-triazolo[4,3-a]quinolin-1-one [ No CAS ]
  • C22H20N4O3 [ No CAS ]
  • 24
  • [ 389621-84-5 ]
  • [ 1367874-63-2 ]
  • [ 1367875-45-3 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; acetonitrile; at 140℃; for 0.833333h;Inert atmosphere; Microwave irradiations; Step 2Morphono{4-(4-{tetra ydro-2H-pyrar)-4-yo y)- 1 H-pyrazolo[4, 3-c]pyridin-3- yl)phenyl)methanoneThe title compound was prepared by the procedure described in step 2 of Example 132. LC- MS (Method G): m/z = 409 [M+H ; 3.42 min. 1H-NMR (400 MHz, DMSO): delta 13.59 (br s, 1 H), 8.04 (d, J = 7.8, 2H), 7.90 (d, J = 5.9, 1 H), 7.52 (d, J = 7.8, 2H), 7.15 (d, J = 6.0, 1 H), 5.50 - 5.48 (m, 1 H), 3.79 - 3.70 (m, 2H), 3.69 - 3.34 (m, 9H), 2.05 (br d, J = 12.4, 2H), 1.73 - 1.67 (m, 2H).
  • 25
  • [ 389621-84-5 ]
  • [ 1366131-41-0 ]
  • N-[5-{2-amino-3-[4-(4-morpholinylcarbonyl)phenyl]-6-quinolinyl}-4-methyl-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; at 80℃; for 29h;Inert atmosphere; A mixture of potassium acetate (20 mg, 0.20 mmol), N-[5-(2-amino-3-bromo-6- quinolinyl)-4-methyl-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (23 mg, 0.04 mmol) and [4-(4-morpholinylcarbonyl)phenyl]boronic acid (12 mg, 0.05 mmol) was placed in a sealed tube and sparged with N2 before the addition of PdCI2(dppf)-CH2CI2 adduct (4 mg, 0.005 mmol). The mixture was heated at 80C for 5 hours. A second portion of PdCI2(dppf)-CH2CI2 adduct (4 mg, 0.005 mmol) and [4-(4-morpholinylcarbonyl)phenyl]boronic acid (12 mg, 0.05 mmol) was added and the mixture was sparged then heated in a 80C sand bath for 24 hours. The mixture was partitioned between EtOAc and water. The organic layer was dried with Na2S04, filtered and concentrated. The residue was purified by reverse phase chromatography eluting with 20-90% MeCN water. Fractions containing the product were combined and concentrated. The residue was slurried in DCM hexanes to yield //-[5-{2-amino-3-[4-(4- morpholinylcarbonyl)phenyl]-6-quinolinyl}-4-methyl-2-(methyloxy)-3-pyridinyl]-2,4- difluorobenzenesulfonamide (10 mg, 36%) as a white solid. 1H NMR (400 MHz, DMSO-c/6) delta ppm 8.18 (s, 1 H) 7.94 (d, J=3.9 Hz, 2 H) 7.77 - 7.66 (m, 2 H) 7.65 - 7.56 (m, 4 H) 7.56 - 7.50 (m, 2 H) 7.47 (dd, J=8.6, 2.0 Hz, 1 H) 7.21 (td, J=8.4, 2.0 Hz, 1 H) 6.23 (br s, 2H) 3.74- 3.47 (br s, 8 H) 3.40 (s, 3 H) 2.30 (s, 3 H). LCMS: m/z 646 (M+1 )+. HRMS for C33H3oF2N505S (M + H)+ calc: 646.1936, found: 646.1934
  • 28
  • [ 389621-84-5 ]
  • [ 873078-77-4 ]
  • morpholin-4-yl-(4-{5-phenyl-4-[(tetrahydrofuran-2-ylmethyl)-amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-phenyl)-methanone [ No CAS ]
  • 29
  • [ 389621-84-5 ]
  • [ 1314883-33-4 ]
  • [ 1314882-62-6 ]
  • 30
  • [ 389621-84-5 ]
  • [ 1416315-14-4 ]
  • 31
  • [ 389621-84-5 ]
  • [ 1314882-87-5 ]
  • 32
  • [ 389621-84-5 ]
  • [ 697300-73-5 ]
  • [ 1416315-09-7 ]
  • 33
  • [ 389621-84-5 ]
  • [ 59489-71-3 ]
  • [ 1000067-96-8 ]
YieldReaction ConditionsOperation in experiment
44.88% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 20℃; for 16h;Inert atmosphere; Reflux; To the solution of a 5-bromo-pyrazine-2-amine according to formula (1.5 g, 8.62 mmol) in 1 ,4-dioxane (20 ml) was added a boronic acid of formula (vi) such as 4-(morpholine- 4-carbonyl)phenylboronic acid (CombiBlocks) (2.046 g, 8.70 mmol) at RT and the resulting mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium (Il)chloride (423 mg, 0.60 mmol) and 1 M aqueous solution of potassium carbonate (10.34 ml, pre-purged with N2 gas) were added to the reaction mixture. The reaction mixture was heated to reflux for 16 h, cooled to RT and concentrated under vacuum. 5 ml of water was added to the reaction mixture and extracted with ethyl acetate (20 ml X 4). Combined organic layers were washed with brine solution (5 ml), dried over anhydrous Na2S04 and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using 2% of MeOH in DCM as an eluent to yield a 5 -substituted pyrazine-2- amine of formula (vii) (1.1 g, 44.88%) as pale yellow solid.
 

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