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Structure of 1201644-51-0

Chemical Structure| 1201644-51-0

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Product Details of [ 1201644-51-0 ]

CAS No. :1201644-51-0
Formula : C15H21BN2O3
M.W : 288.15
SMILES Code : O=C1N(C2=NC=C(B3OC(C)(C)C(C)(C)O3)C=C2)CCC1
MDL No. :MFCD12032530
InChI Key :UCMAEVWLVAOKRQ-UHFFFAOYSA-N
Pubchem ID :45786487

Safety of [ 1201644-51-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 1201644-51-0 ]

* 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 [ 1201644-51-0 ]

[ 1201644-51-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 928775-04-6 ]
  • [ 73183-34-3 ]
  • [ 1201644-51-0 ]
YieldReaction ConditionsOperation in experiment
47% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80.0℃;Inert atmosphere; Intermediate 33 (214 mg, 0.89 mmol) was placed in a 10 mL flask. Bis(pinacolato)diborane (451 mg, 2.0 eq.) was added, followed by KOAc (261 mg, 3.0 eq.) and the catalyst (67 mg, 0.1 eq.). The flask was purged with N2 and DMSO (3 mL) was added. The mixture was degassed for 1 h before heating up to 80 C. and keeping this temperature o.n. The mixture was diluted with EtOAc and passed through a short Celite pad. The Celite was washed with EtOAc, and the filtrate was concentrated and washed with brine. The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by column (EtOAc/petroleum ether=1:3 to 1:1). The desired product (Intermediate 34) was obtained as a white solid (120 mg, 47%). 1HNMR (400 MHz, DMSO-d6, ppm): 8.57 (d, J=0.8 Hz, 1H); 8.33 (dd, J=8.4, 0.8 Hz, 1H); 8.00 (dd, J=8.4, 1.6 Hz, 1H); 4.00 (t, J=7.2 Hz, 2H); 2.60 (t, J=8.0 Hz, 2H); 2.05 (m, 2H), 1.31 (m, 12H).
  • 2
  • [ 1217273-57-8 ]
  • [ 1201644-51-0 ]
  • [ 1217272-99-5 ]
YieldReaction ConditionsOperation in experiment
33% With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 70.0℃;Inert atmosphere; Intermediate 34 (120 mg, 0.42 mmol) was mixed with Intermediate 18 (142 mg, 1.2 eq.), K2CO3 (115 mg, 2.0 eq.) and PdCl2(dppf)DCM (34 mg, 0.1 eq.). The flask was purged with N2, and 6 mL of 1,4-dioxane was added. The mixture was degassed for 1 h at r.t. and then heated at 70 C. o.n. The mixture was passed through a Celite pad and washed with EtOAc. The filtrate was concentrated and washed with brine. The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by column (EtOAc/petroleum ether=3:1 to 100% EtOAc). The desired product was obtained as a solid (50 mg, 33%). 1H NMR (400 MHz, DMSO-d6, ppm): δ 8.67 (d, J=2.0 Hz, 1H); 8.37 (d, J=8.8 Hz, 1H); 8.09 (dd, J=8.8, 2.8 Hz, 1H); 7.65 (s, 1H); 7.60 (d, J=8.0 Hz, 1H); 7.34 (d, J=8.0 Hz, 1H); 5.29 (s, 1H); 4.72 (m, 1H); 4.65 (dd, J=16.4, 9.2 Hz, 1H); 4.04 (t, J=7.2 Hz, 2H); 3.74 (m, 2H); 3.28 (m, 2H); 2.61 (t, J=8.0 Hz, 2H); 2.07 (m, 2H). MS (m/z): 366 [M+H].
  • 3
  • [ 1201644-51-0 ]
  • [ 1354355-93-3 ]
  • [ 1354354-68-9 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 96.0℃;Inert atmosphere; Sealed tube; [0224] Step 2: A mixture of 5-bromo-N-((2'-(trifluoromethyl)-[2,4'-bipyridin]-5- yl)methyl)picolinamide 72-1 (22 mg, 0.05 mmol), l-(5-(4,4,5,5-tetramethyl- l,3,2- dioxaborolan-2-yl)pyridin-2-yl)pyrrolidin-2-one 72-2 (29 mg, 0.1 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol) and K3P04 (21 mg, 0.1 mmol) in dioxane (0.5 mL) and water (0.1 mL) was stirred at 96 C under argon overnight. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate) and the filtrate was redistributed between ethyl acetate and water. The organic phase was dried over Na2S04 and concentrated with rotavap. The residue was subjected to preparative reverse phase HPLC separation to give 6'-(2- oxopyrrolidin-l-yl)-N-((2'-(trifluoromem^carboxamide 72 as a solid. MS m/z 519.2 (M + 1). 1H NMR 400 MHz (CDC13) δ 8.83 (d, 1 H), 8.79 (d, 1 H), 8.76 (dd, 1 H), 8.62 (dd, 1 H), 8.57 (dd, 1 H), 8.52 (t, 1 H), 8.34-8.29 (m, 2 H), 8.10-8.02 (m, 2 H), 7.96-7.88 (m, 2 H), 7.84 (d, 1 H), 4.79 (d, 2 H), 4.16 (t, 2 H), 2.71 (t, 2 H), 2.18 (t, 2 H).
  • 4
  • [ 1201644-51-0 ]
  • 4-(5-chloro-8-[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile [ No CAS ]
  • 4-{8-[(3R)-1-methylpiperidin-3-yl]methoxy}-5-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyrazin-6-yl}benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium(II); In 1,4-dioxane; water; at 90.0℃; for 3.0h;Inert atmosphere; A mixture of 4-(5-chloro-8-[(3R)-1-methylpiperidin-3-yl]methoxy}imidazo[1,2-a]pyrazin-6-yl)benzonitrile (47. mg, 0.12 mmol), potassium phosphate (78 mg, 0.37 mmol), dichloro[1,1'-bis(dicyclohexylphosphino)ferrocene]palladium(II) (9.3 g, 0.012 mmol), 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]pyrrolidin-2-one (JPM2 Pharma, cat No.JPM2-00-744: 42 mg, 0.15 mmol) in 1,4-dioxane (3 mL) and water (1 mL) was purged with nitrogen then stirred at 90 C. for 3 h. The reaction mixture was cooled to room temperature then extracted with DCM.
  • 5
  • [ 1201644-51-0 ]
  • (S)-3-(7-chloro-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)-5-(difluoromethyl)-4-fluoro-N-methylbenzamide [ No CAS ]
  • (S)-3-(difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(2-oxopyrrolidin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate; In water; N,N-dimethyl-formamide; at 110.0℃; for 0.5h; A sample of (S)-3-(7-chloro-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)-5-(difluoromethyl)-4-fluoro-N-methylbenzamide (15 mg, 0.034 mmol, see Example 26, Step 1) was dissolved in DMF (0.4 ml) and water (0.08 ml). This solution was treated with <strong>[1201644-51-0]1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrrolidin-2-one</strong> (29 mg, 0.10 mmol) and K2CO3 (14 mg, 0.10 mmol). Pd XPhos G2 (4 mg, 5 μmop was added, the vial was capped, and the solution was stirred at 110 C. After 30 mins, LCMS indicated consumption of the starting material. The solution was cooled to room temperature, diluted with MeCN and water, filtered through a SiliaPrep Thiol cartridge, and purified by HPLC (pH=2 method) to provide (S)-3-(difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(2-oxopyrrodin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide (1.7 mg, 3.0 μmol, 9% yield). LCMS calculated for C28H26F3N6O4 (M+H)+: m/z=567.2; found: 566.9.
 

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