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[ CAS No. 877399-35-4 ] {[proInfo.proName]}

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Chemical Structure| 877399-35-4
Chemical Structure| 877399-35-4
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Product Details of [ 877399-35-4 ]

CAS No. :877399-35-4 MDL No. :MFCD18383285
Formula : C17H28BN3O4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :JGJAAWHJOWNRBD-UHFFFAOYSA-N
M.W : 349.23 Pubchem ID :54576812
Synonyms :

Safety of [ 877399-35-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 877399-35-4 ]

* 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 [ 877399-35-4 ]

[ 877399-35-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 877399-34-3 ]
  • [ 73183-34-3 ]
  • [ 877399-35-4 ]
YieldReaction ConditionsOperation in experiment
97% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; tert-Butyl 3-[4-(4,4,5,5-tetramethyl-1,3-dioxoborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (2-8): A reaction mixture of compound (2-6) (225 mg, 0.74 mmol) and bis(pinacolate)diboron (2-7, 227 mg, 0.89 mmol) with KOAc (247 mg, 2.52 mmol) in 3 mL of DMSO was purged with N2 for 15 minutes, then PdCl2(dppf)2CH2Cl2 (30 mg, 2.52 mmol) was added. The resulting mixture was stirred at 80 C. under N2 for overnight. After it cooled down to room temperature, the mixture was filtered through Celite pad and washed well with EtOAc. The filtrate was extracted with H2O (2*50 mL), brine (50 mL). The organic layer was dried (Na2SO4), then concentrated by vacuum. The residue was then filtered through silica gel pad, eluted with hexane:EtOAc/3:2. The filtrate was concentrated by vacuum to give 250 mg of 2-8) as a clear oil (97% yield). 1H NMR (400 MHz, chloroform-D) δ ppm 1.18-1.27 (m, 9H) 1.28-1.34 (m, 6H) 1.41-1.49 (m, 6H) 4.22-4.33 (m, 2H) 4.36 (t, J=8.59 Hz, 2H) 4.98-5.13 (m, 1H) 7.83 (s, 2H).
97% With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dichloromethane; dimethyl sulfoxide; at 80℃; A reaction mixture of compound (2-6) (225 mg, 0.74 mmol) and bis(pinacolate)diboron (2-7, 227 mg, 0.89 mmol) with KOAc (247 mg, 2.52 mmol) in 3mL of DMSO was purged with N2 for 15 minutes, then PdCl2(dppf)2CH2CI2 (30 mg, 2.52 mmol) was added. The resulting mixture was stirred at 80C under N2 for overnight. After it cooled down to room temperature, the mixture was filtered through Celite pad and washed well with EtOAc. The filtrate was extracted with H2O (2 x 50 mL), brine (50 mL). The organic layer was dried (Na2SO4), then concentrated by vacuum. The residue was then filtered through silica gel pad, eluted with hexane:EtOAc/3:2. The filtrate was concentrated by vacuum to give 250 mg of (2-8) as a clear oil (97% yield). 1H NMR (400 MHz, chloroform-D) 5 ppm 1.18 - 1.27 (m, 9 H) 1.28 - 1.34 (m, 6 H) 1.41 -1.49 (m, 6 H) 4.22 - 4.33 (m, 2 H) 4.36 (t, J=8.59 Hz, 2 H) 4.98 - 5.13 (m, 1 H) 7.83 (s, 2 H).
  • 2
  • [ 756520-48-6 ]
  • [ 877399-35-4 ]
  • [ 877399-36-5 ]
YieldReaction ConditionsOperation in experiment
92% fert-Butyl 3-(4-{6-amino-5-[1 -(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl}-1 H-pyrazol-1 -yl)azetidine-1-carboxylate (2-10): A reaction mixture of compound (2-8) (459 mg; 1.31 mmol) and 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amine (2-9) (374 mg; 0.88 mmol) in 13 mL of ethylene glycol dimethylether, anhydrous (DME) was purged with N2 for 15 minutes, then Pd(ll)(PPh3)2CI2 (46 mg, 0.07 mmol) was added and continued to purge with N2 for another 15 minutes. Another 1.0 N Na2CO3 solution (3.9 mL; 3.9 mmol) was added after purging with N2 for 15 minutes. The resulting mixture was stirred at 85C under N2 for overnight. The reaction mixture was filtered through Celite pad and washed well with MeOH. The filtrate was concentrated by vacuum. The residue was partitioned between EtOAc (200 mL) and saturated NaHCO3 solution (2 x 50 mL); brine (50 mL). The organic layer was dried (Na2SO,i), then concentrated by vacuum. The residue was purified by Biotage system (25 M, 100% CH2CI2; 100% CH2CI2to 90% CH2CI2 with 10% MeOH) to collect the desired fraction to afford 421 mg of (2-10) as a brown color grease (92% yield). 1H NMR (400 MHz, chloroform-D) 5 ppm 1.17 -1.26 (m, 9 H) 1.80 - 1.87 (m, 3 H) 4.04 - 4.18 (m, 2 H) 4.20 - 4.33 (m, 2 H) 4.34 - 4.41 (m, 1 H) 4.79 (s, 2 H) 5.02 (d, J=7.58 Hz, 1 H) 7.04 (t, J=8A6 Hz, 1 H) 7.33 - 7.41 (m, 1 H) 7.44 - 7.52 (m, 1 H) 7.53 - 7.58 (m, 1 H) 7.59 - 7.65 (m, 1 H) 7.72 - 7.78 (m, 1 H); LCMS calcd for C24H26CI2FN5O3 (M+H) 523, found 523.
63 - 92% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; at 85℃; A reaction mixture of compound (-8) (459 mg; 1.31 mmol) and 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amine (-9) (374 mg; 0.88 mmol) in 13 mL of ethylene glycol dimethylether, anhydrous (DME) was purged with N2 for 15 minutes, then Pd(II)(PPh3)2Cl2 (46 mg, 0.07 mmol) was added and continued to purge with N2 for another 15 minutes. Another 1.0 N Na2CO3 solution (3.9 mL; 3.9 mmol) was added after purging with N2 for 15 minutes. The resulting mixture was stirred at 85 C. under N2 for overnight. The reaction mixture was filtered through Celite pad and washed well with MeOH. The filtrate was concentrated by vacuum. The residue was partitioned between EtOAc (200 mL) and saturated NaHCO3 solution (2x50 mL); brine (50 mL). The organic layer was dried (Na2SO4), then concentrated by vacuum. The residue was purified by Biotage system (25 M, 100% CH2Cl2; 100% CH2Cl2 to 90% CH2Cl2 with 10% MeOH) to collect the desired fraction to afford 421 mg of (2-10) as a brown color grease (92% yield). 1H NMR (400 MHz, chloroform-D) ? ppm 1.17-1.26 (m, 9H) 1.80-1.87 (m, 3H) 4.04-4.18 (m, 2H) 4.20-4.33 (m, 2H) 4.34-4.41 (m, 1H) 4.79 (s, 2H) 5.02 (d, J=7.58 Hz, 1H) 7.04 (t, J=8.46 Hz, 1H) 7.33-7.41 (m, 1H) 7.44-7.52 (m, 1H) 7.53-7.58 (m, 1H) 7.59-7.65 (m, 1H) 7.72-7.78 (m, 1H); LCMS calcd for C24H26Cl2FN5O3 (M+H) 523, found 523.
  • 3
  • [ 269410-08-4 ]
  • [ 141699-58-3 ]
  • [ 877399-35-4 ]
YieldReaction ConditionsOperation in experiment
NaH (60% in mineral oil, 222 mg, 5.6 mmol) is added portionwise to a stirred solution of A- (4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.10 g, 5.56 mmol) in DMF (20 ml). The resulting mixture is stirred for 1 h at O0C and then allowed to warn to RT. A solution of 3-Methanesulfonyloxy-azetidine-i-carboxylic acid tert-butyl ester (as obtained in <n="61"/>preparation 80, 1.39 g, 5.56 mmol) in DMF (3 ml) is then added dropwise. After complete addition, the reaction mixture is heated at 95C for 5h. The reaction is quenched with water and extracted with EtOAc several times. The combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography on a 40 g silica gel column on a Combiflash Companion (Isco Inc.) apparatus ( gradient CH2CI2: TBDME from 1 :0 => 0:1 ) to afford the title compound as a colorless foam, R1 = 1.200 min (Acquity UPLC BEH C18, 2.1x50mm, 1.7 micron, detection 215nM, 0.1 min 2% CH3CN in H2O , 2% to 100% CH3CN in H2O in 1.5min, 0.4 min 100% CH3CN + 0.1% TFA, flow rate 1.Oml/min); MS: 350 (M+1)+ .
Stage 146.3 <n="119"/>; 3-[4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-azetidine-1-carboxylic acid tert-butyl ester; The title compound was prepared as described in published patent application WO 2008148867: To a solution of 1-BOC-3-hydroxyazetidine (1.0 g, 5.77 mmol), 4-dimethylaminopyridine (7 mg, 0.058 mmol) and triethylamine (0.880 ml_, 6.35 mmol) in DCM (15 mL) cooled at 0 0C was added dropwise methanesulfonyl chloride (0.45 mL, 5.77 mmol). The RM was stirred 18 h at rt, diluted with DCM, washed with a solution of saturated NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure. 3-Methanesulfonyloxy-azetidine-i-carboxylic acid tert-butyl ester obtained as an oil was used directly in the next step.To a solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.4 g 5.57 mmol) in DMF (20 mL) stirred at 0 0C was added sodium hydride (55 % in oil, 0.243 g, 5.57 mmol). After addition the mixture was stirred 1 h at rt, a solution of the above obtained 3- methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester (1.4 g, 5.57 mmol) in DMF (3 mL) was added. The RM was stirred 30 min at rt, and then 3 h at 95 0C. After cooling at rt the mixture was poured in ice water and extracted with EtOAc. The combined organic phases were washed with a solution of saturated NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (with heptane and EtOAc as eluants) to afford the title compound as an oil (tR 4.33 min (conditions 3), MH+ = 350.1)
With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 14h;Inert atmosphere; A solution of 4-(4.4.5.5-tctramcthyl- 1.3.2-dioxaborolan-2-yl)- 1H-pyrazolc (1.24 g, 6.37 mmol), tert- butyl 3-[(methanesulfonyl)oxy]azetidine-l-carboxylate (1.60 g, 6.37 mmol) and caesium carbonate (3.32 g, 10.2 mmol) in N.N-d i m c th y 1 fo rm am i dc (15 ml) was stirred at 100 C under argon for 14 h. The reaction mixture is mixed with water and filtered. The filtrate was purified directly by HPLC to yield 513 mg (87 % purity, 20 % yield) of the title compound.LC-MS (method 2): Rt= 1.12 min; MS (ESIpos): m/z = 350 [M+H]+-NMR (600 MHz, DMSO-d6) d [ppm]: 1.25 (s, 12H), 1.40 (s, 9H), 4.06 - 4.15 (m, 2H), 4.22 - 4.31 (m, 2H), 5.19 - 5.25 (m, 1H), 7.71 (s, 1H), 8.07 (s, 1H).
  • 4
  • [ 877399-35-4 ]
  • [ 1185767-66-1 ]
  • [ 1185767-36-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; at 95℃; for 2h; Stage 146.2; 3-{4-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1 ,2-b]pyridazin-6-yl]-pyrazol-1-yl}-azetidine-1- carboxylic acid tert-butyl ester; A flask was charged with 6-(6-chloro-imidazo[1 ,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 173.1, 100 mg, 0.320 mmol), 3-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- pyrazol-1-yl]-azetidine-1-carboxylic acid tert-butyl ester (Stage 146.3), 168 mg, 0.480 mmol), DME (2 mL), Pd(PPh3)2CI2 (11 mg, 0.05 mmol) and 2 M K2CO3 (432 μl_, 0.863 mmol). The RM was heated at 95 0C for 2 h. The cool RM was diluted with EtOAc / NaHCO3. The organic phase was separated and washed with brine (2X) then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (CombiFlash Companion system, with a 4 g RediSep silica gel column, DCM / (DCM / MeOH 19:1 ) = 100:0 -} 0:100) to afford the title compound as a foam (tR 4.33 min (conditions 3), MH+ = 500.1).
YieldReaction ConditionsOperation in experiment
94.6% With caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 16h; General procedure: A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (LXI) (0.2 g, 1.031 mmol), tert-butyl 3-fluoro-4-((methylsulfonyl)oxy)piperidine-1l-carboxylate (LXIV) (0.337 g, 1.134 mmol) and Cs2CO3 (0.470 g, 1.443 mmol) in DMF (4 mL) was heated at 90 C. for 16 h. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The organic layer was washed with water, brine, and dried over anhydrous sodium sulfate and concentrated. The crude product was purified on a silica gel column (EtOAc/Hexanes 0%→100%) to give tert-butyl 3-fluoro-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl) piperidine-1-carboxylate (LXV) as a colorless oil (210 mg, 0.531 mmol, 51.5% yield). Used in the next step w/o further purification. ESIMS found for C19H31BFN3O4 m/z 396.2 (M+H).
  • 6
  • [ 756503-69-2 ]
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  • [ 877399-36-5 ]
  • 7
  • [ 756503-69-2 ]
  • [ 877399-35-4 ]
  • [ 877399-38-7 ]
  • 9
  • [ 141699-58-3 ]
  • [ 877399-35-4 ]
  • 10
  • [ 877399-35-4 ]
  • [ 1422126-03-1 ]
  • [ 1422126-25-7 ]
YieldReaction ConditionsOperation in experiment
13 mg With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; 1,4-dioxane (2 mL) and a 2 M aqueous sodium carbonate solution (94 μL) were added to the compound 0001-5 (21 mg), <strong>[877399-35-4]tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate</strong> (44 mg, which was synthesized according to Journal of Medicinal Chemistry, 2011, 54, 6342), and bis(di-tert-butyl (4-dimethylaminophenyl)phosphine)dichloropalladium (II) (4.4 mg) under a nitrogen air flow, and the mixture was stirred at 100C overnight. The reaction solution was cooled, water was then added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform-methanol) to obtain a compound 0143-1 (13 mg) as a white solid. MS m/z (M+H): 478.
  • 11
  • [ 877399-35-4 ]
  • (S)-methyl 6-bromo-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]
  • methyl (S)-6-(1-(1-(tert-butoxycarbonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Step 1. Methyl (S)-6-(l-(l-(tert-butoxycarbonyl)azetidin-3-yl)-lH-pyrazol-4-yl)-5-cyclobutoxy- 2-methyl-3,4-dihydroquinoline-l(2H)-carboxylate [0596] A mixture of methyl (S)-6-bromo-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-l(2H)- carboxylate (0.096 g, 0.254 mmol), tert-butyl 3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH- pyrazol- 1 -yl)azetidine- 1 -carboxylate (0.113 g, 0.325 mmol), and cesium carbonate (0.264 g, 0.81 1 mmol) in dioxane (2.0 mL) and water (0.40 mL) was purged with nitrogen to remove any oxygen. XPhos Precatalyst 2nd Generation (0.020 g, 0.027 mmol) was added and the reaction was purged with nitrogen and then heated at 100 C for 16 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was separeated and extracted with ethyl acetate, and the combined organic phases were concentrated to afford an oil. This material was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 25-50% ethyl acetate -hexane) to afford methyl (S)-6-(l-(l-(tert-butoxycarbonyl)azetidin-3-yl)-lH-pyrazol-4-yl)-5-cyclobutoxy-2-methyl-3,4- dihydroquinoline-l(2H)-carboxylate (0.132 g, 98%) as a colorless oil. MS (ESI, pos. ion) m/z 497 [M+H]+.
  • 12
  • [ 877399-35-4 ]
  • methyl (S)-6-bromo-5-(4-fluorophenoxy)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]
  • methyl (S)-6-(1-(1-(tert-butoxycarbonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-5-(4-fluorophenoxy)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16h; Step 2. Methyl-(S)-6-(l-(l-(tert-butoxycarbonyl)azetidin-3-yl)-lH-pyrazol-4-yl)-5-(4- fluorophenoxy)-2-methyl-3,4-dihydroquinoline-l(2H)-carboxylate [0592] A mixture of methyl (S)-6-bromo-5-(4-fiuorophenoxy)-2-methyl-3,4-dihydroquinoline- l(2H)-carboxylate (0.100 g, 0.254 mmol), tert-butyl 3-(4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)-lH-pyrazol-l-yl)azetidine-l-carboxylate (0.106 g, 0.304 mmol), XPhos Precatalyst 2nd Generation (0.004 g, 0.005 mmol), and cesium carbonate (0.246 g, 0.761 mmol) in 1,4-dioxane (2.0 mL) and water (0.40 mL) was heated at 100 C for 16 h. The reaction mixture was filtered through Celite and concentrated to afford a green oil. This material was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 25-50% ethyl acetate-hexane) to afford methyl (S)-6-(l-(l-(tert-butoxycarbonyl)azetidin-3-yl)-lH-pyrazol-4-yl)-5-(4-fluorophenoxy)-2- methyl-3,4-dihydroquinoline-l(2H)-carboxylate (0.098 g, 72%) as a colorless oil. MS (ESI, pos. ion) m/z 537 [M+H]+.
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; ;