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[ CAS No. 153747-97-8 ]

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Chemical Structure| 153747-97-8
Chemical Structure| 153747-97-8
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CAS No. :153747-97-8 MDL No. :MFCD07369772
Formula : C14H20BrN3O2 Boiling Point : 433°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :342.23 g/mol Pubchem ID :11244775
Synonyms :

Safety of [ 153747-97-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 153747-97-8 ]

  • Upstream synthesis route of [ 153747-97-8 ]
  • Downstream synthetic route of [ 153747-97-8 ]

[ 153747-97-8 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 624-28-2 ]
  • [ 57260-71-6 ]
  • [ 153747-97-8 ]
YieldReaction ConditionsOperation in experiment
82% With tris-(dibenzylideneacetone)dipalladium(0); [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; sodium t-butanolate In toluene at 80℃; for 4 h; Sealed tube; Inert atmosphere To a stirred solution of 2,5-dibromopyridine (2 g, 10.7 mmol), sodium tert-butoxide (1.6 g,16.6 mmol), xantphos (400 mg, 0.7 mmol) and toluene (100 mL) in sealed tube argon waspurged for 5 min. To the reaction mixture tert-butyl piperazine-1-carboxylate (3 .4 g, 14.30mmol) followed by Pd2(dba)3 (200 mg, 0.21 mmol) was added and heated at 80 °C for 4 h(TLC indicated complete consumption of starting material). The reaction mixture was dilutedwith EtOAc (200 mL), water (100 mL), filtered through Celite bed and washed with EtOAc(2 x 30 mL). The combined organic extracts were washed with brine (50 mL), dried overNa2S04 and concentrated under reduced pressure to give the crude product which waspurified by column chromatography (100-200 silica gel, 50 g, 10-20percent EtOAc-hexanes) toafford tert-butyl4-(5-bromo-2-pyridyl)piperazine-1-carboxylate (3 g, 82percent) as a yellow solid.LCMS (ESI+ ): m/z: 342.57 [M+Ht.
Reference: [1] Organic Letters, 2003, vol. 5, # 24, p. 4611 - 4614
[2] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 123
[3] Patent: WO2007/20888, 2007, A1, . Location in patent: Page/Page column 45-46
[4] Patent: US2006/293310, 2006, A1, . Location in patent: Page/Page column 5
  • 2
  • [ 53939-30-3 ]
  • [ 57260-71-6 ]
  • [ 153747-97-8 ]
YieldReaction ConditionsOperation in experiment
81.5% With potassium carbonate In acetonitrile at 110℃; for 12 h; General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 °C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7percent).; The title compound was prepared using tert-butyl piperazine-1-carboxylate (1.45 g, 7.79 mmol),5-bromo-2-chloropyridine (1.00 g, 5.20 mmol) and potassium carbonate (1.44 g, 10.39 mmol) in acetonitrile (30 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (1.45 g, 8 1.5percent).MS (ESI, pos. ion) m/z: 342.1 [M+H] and‘H NMR (600 MHz, CDC13): (ppm) 8.17 (d, J 2.4 Hz, 1H), 7.52 (dd, J 9.0, 2.5 Hz, 1H), 6.52 (d, J 9.0 Hz, 1H), 3.55 - 3.49 (m, 4H), 3.49 - 3.45 (m, 4H), 1.46 (s, 9H).
58.8% at 80℃; for 14 h; To a stirred solution of 1-Boc piperazine (10.6 g, 57.29 mmol, Symax fine chemicals) in dryDMF (lOOmL), TEA (14.43 mL, 103.39 mmol) and 5-bromo-2-chloropyrimidine (10 g, 52.08mmol, Oakwood chemicals) were added and the reaction mixture was stirred at 80°C for 14h. It was cooled down to rt and poured on iced water (100 mL). The resulting precipitatewas filtered and washed with hexane (50 mL) to afford the title compound. Yield: 58.8percent(10 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 68.60(s, IH), 8.13 (dd, J= 8.6, 2.4Hz, IH), 7.54 (dd, J = 8.4, 0.4 Hz, IH), 3.22-3.20 (m, 4H), 2.61-2.59 (m, 4H), 1.42 (5, 9H).LCMS: (Method A) 343.9 (M +2H), Rt. 5.58 mm, 98.9percent (Max).
58.8% With triethylamine In N,N-dimethyl-formamide at 80℃; for 14 h; To a stirred solution of 1-Boc piperazine (10.6 g, 57.29 mmol, Symax fine chemicals) in dry DMF (100mL), TEA (14.43 mL, 103.39 mmol) and 5-bromo-2-chloropyridine (10 g, 52.08 mmol, Oakwood chemicals) were added and the reaction mixture was stirred at 80°C for 14 h. It was cooled down to rt and poured on iced water (100 mL). The resulting precipitate was filtered and washed with hexane (50 mL) to afford the title compound. Yield: 58.8percent (10 g, off white solid). 1H NMR (400 MHz, DMSO-d6): δ 8.60 (s, 1 H), 8.13 (dd, J = 8.6, 2.4 Hz, 1 H), 7.54 (dd, J = 8.4, 0.4 Hz, 1 H), 3.22-3.20 (m, 4H), 2.61 -2.59 (m, 4H), 1.42 (s, 9H). LCMS: (Method A) 343.9 (M +2H), Rt. 5.58 min, 98.9percent (Max).
Reference: [1] Patent: WO2016/192657, 2016, A1, . Location in patent: Page/Page column 65
[2] Patent: WO2017/144633, 2017, A1, . Location in patent: Page/Page column 111
[3] Patent: WO2017/144639, 2017, A1, . Location in patent: Page/Page column 96
  • 3
  • [ 766-11-0 ]
  • [ 57260-71-6 ]
  • [ 153747-97-8 ]
YieldReaction ConditionsOperation in experiment
87.66% With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12 h; Step 1: K2CO3 (2.76 g, 20 mmol) was added into a mixture of 270-2 (1.76 g, 10 mmol) and 270-1 (2.24 g, 12 mmol) in DMF (20 mL). The mixture was stirred at 110°C for 12h, poured into H2O (100 mL). The obtained mixture was extracted with EtOAc (150 mL×3). The organic phases were combined and washed with brines (150 mL), dried over anhydrous sodium sulfate, filtrated, and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=7:1) to deliver 270-3 (3 g, yield 87.66percent) as colorless oil. MS ESI calcd for C14H2OBrN3O2 [M+H]+ 342, found 342.
Reference: [1] Patent: EP3124482, 2017, A1, . Location in patent: Paragraph 0711; 0712
[2] Patent: US2012/184520, 2012, A1, . Location in patent: Page/Page column 17
  • 4
  • [ 24424-99-5 ]
  • [ 73406-97-0 ]
  • [ 153747-97-8 ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine In dichloromethane at 0 - 20℃; [0949] To a solution ofcompound 90a (125 g, 516 mmol) inDCM (300mL), TEA (104 g, 1.03 mol) was added, followedby (BOC) 2 0 (135 g, 619 mmol) in portions with stirring at ooC. The resulting mixture was stirred overnight at room temperature. The reaction was then quenched with water (1 00mL), and the product was extracted with DCM (3x150 mL).The combined organic layers were concentrated underreduced pressure to obtain compound 90b as a white solid(125 g, 71percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C14H20BrN3 0 2 : 342.1 (M+H). found 342.1.
Reference: [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0948-0949
[2] Patent: CN104650049, 2018, B, . Location in patent: Paragraph 0359; 0360
  • 5
  • [ 53939-30-3 ]
  • [ 57260-71-6 ]
  • [ 633283-53-1 ]
  • [ 153747-97-8 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 24, p. 4611 - 4614
  • 6
  • [ 53939-30-3 ]
  • [ 153747-97-8 ]
Reference: [1] Patent: US2014/364414, 2014, A1,
  • 7
  • [ 766-11-0 ]
  • [ 153747-97-8 ]
Reference: [1] Patent: CN104650049, 2018, B,
  • 8
  • [ 73183-34-3 ]
  • [ 153747-97-8 ]
  • [ 496786-98-2 ]
YieldReaction ConditionsOperation in experiment
56% With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; Inert atmosphere [0951] A solution ofcompound 90b (125 g, 366 mmol) inDMF (1.30 L)was treatedwith, 4,4,4',4',5,5,5',5'-octamethyl2,2'-bi(1,3,2-dioxaborolane) (186 g, 732 mmol), Pd(OAc) 2(4.09 g, 18.3 mmol), PPh3 (19.2 g, 73.2 mmol) and KOAc(108 g, 1.10 mol) under a nitrogen atmosphere. The resultingmixture was stirred overnight at 80° C. Upon cooling to roomtemperature, the solids were collected by filtration. The filtrate was concentratedunderreduced pressure, and the resultant residue was purified by flash colunm chromatography onsilica gel (EtOAc/petroleum ether (1 :50 v/v)) to obtain compound 90c as a white solid (80.0 g, 56percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H32BN3 0 4 : 390.2(M+H). found 390.2.
2.55 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 2 h; Inert atmosphere Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (2.0 g, 5.84 mmol),Bis(boronic acid) pinacol ester (2.2 g, 8.77 mmol) andPotassium acetate (1.72 g, 17.53 mmol)To a solution of dimethyl sulfoxide (10 mL) was added Pd(dppf)Cl2.CH2Cl2 (473.0 mg, 0.58 mmol).The reaction was heated to 80°C and stirred for 2 hours.Cool toDiluted with ethyl acetate (100 mL) at room temperature and filtered through celite. The filtrate was washed with saturated brine (100 mL x 4), anhydrousSodium sulfate was dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 3/1) to give the title compoundThe product was an off-white solid (2.55 g, 112percent).
Reference: [1] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0945; 0950-0951
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5361 - 5379
[3] Patent: US2013/225548, 2013, A1, . Location in patent: Paragraph 0531; 0632
[4] Patent: CN104650049, 2018, B, . Location in patent: Paragraph 0426; 0427
  • 9
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Reference: [1] Patent: WO2015/88045, 2015, A1, . Location in patent: Paragraph 0239
[2] Patent: US2017/8885, 2017, A1, . Location in patent: Paragraph 0656; 0658
[3] Patent: WO2017/38909, 2017, A1, . Location in patent: Paragraph 0308; 0309; 0311
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