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[ CAS No. 62150-46-3 ]

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2D
Chemical Structure| 62150-46-3
Chemical Structure| 62150-46-3
Structure of 62150-46-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 62150-46-3 ]

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Related Doc. of [ 62150-46-3 ]

SDS

Product Details of [ 62150-46-3 ]

CAS No. :62150-46-3MDL No. :MFCD04113813
Formula :C6H5BrN2OBoiling Point :333.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :201.02Pubchem ID :693291
Synonyms :

Computed Properties of [ 62150-46-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 62150-46-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 62150-46-3 ]

  • Downstream synthetic route of [ 62150-46-3 ]

[ 62150-46-3 ] Synthesis Path-Downstream   1~10

  • 2
  • [ 62150-46-3 ]
  • [ 84249-14-9 ]
YieldReaction ConditionsOperation in experiment
1.5 kg With bromine; sodium hydroxide; In water; at -10 - 80℃; for 2h;Large scale; third step:Add water to the 50 liter reactor, sodium hydroxide, stir to reduce the temperature to 0 , add bromine, drop the temperature to minus 10 degrees.Add the amide in batches and stir for one hour.Then heat to 80 degrees for one hour.The TCL was detected until the end of the reaction, and the temperature was lowered to room temperature and centrifuged to obtain a crude product which was crystallized from toluene to give a pure product of 1.5 kg.The ratio of each raw material in the third step of Example 1 and the reaction conditions of the third step and the purity and yield of the obtained product are shown in Table 2.
  • 3
  • [ 62150-47-4 ]
  • [ 62150-46-3 ]
YieldReaction ConditionsOperation in experiment
4.5 kg With ammonium hydroxide;Large scale; The second step: 8.5 kg of A was added to 35 liters of ammonia water in batches, methane was stirred overnight, and centrifuged to obtain a crude product which was washed with ethyl acetate and centrifuged to obtain 4.5 kg of amide;
  • 4
  • [ 19524-06-2 ]
  • [ 62150-46-3 ]
  • 5
  • N-(trans-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonyl}cyclohexyl)-5-(trifluoromethyl)pyridin-2-amine [ No CAS ]
  • [ 62150-46-3 ]
  • C24H23F3N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% A mixture of compound 53 (188 mg, 0.37 mmol), <strong>[62150-46-3]4-bromopicolinamide</strong> (75 mg, 0.37 mmol) and 2 M aqueous Na2CO3 (0.6 mL, 1.20 mmol) in DME (3 mL) was degassed in vacuo for 15 min. To the mixture was added Pd(PPh3)4 (48 mg, 0.04 mmol) at room temperature. The mixture was stirred at 100 C under Ar for 8 h. The mixture was poured into water, and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluted with EtOAc in hexane), and crystallized from EtOAc/hexane to give the title compound (62 mg, 33%) as a white solid. mp: 220-222 C. 1H NMR (CDCl3) delta 1.14-1.29 (m, 2H), 1.59-1.76 (m, 2H), 2.20-2.30 (m, 4H), 2.94-3.05 (m, 1H), 3.61-3.75 (m, 1H), 4.60 (d, J = 7.2 Hz, 1H), 5.66 (br s, 1H), 6.34 (d, J = 8.7 Hz, 1H), 7.54 (dd, J = 8.7, 2.3 Hz, 1H), 7.65-7.75 (m, 1H), 7.86-7.94 (m, 3H), 7.99-8.06 (m, 2H), 8.29 (s, 1H), 8.48-8.50 (m, 1H), 8.71 (dd, J = 4.9, 0.8 Hz, 1H). LC/MS m/z 505.1 (M+H). Anal. Calcd for C24H23N4O3SF3: C, 57.13; H, 4.59; N, 11.10. Found: C, 57.04; H, 4.65; N, 10.92.
  • 6
  • 7-tert-butoxycarbonyl-2-exo-(2’-fluoro-3‘-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5’-pyridinyl)-7-azabicyclo[2.2.1]heptane [ No CAS ]
  • [ 62150-46-3 ]
  • C22H25FN4O3 [ No CAS ]
  • 7
  • [ 30766-03-1 ]
  • [ 62150-46-3 ]
  • 8
  • [ 1403941-95-6 ]
  • [ 62150-46-3 ]
  • [ 1403945-75-4 ]
YieldReaction ConditionsOperation in experiment
4.6% With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 190℃; for 22h;microwave irradiation; EXAMPLE 64-((4-Oxo-3-o-tolyl-3,4-dihydropyrrolo[1 ,2-tf[1 ,2,4]triazin-2- yl)methylamino)picolinamideA mixture of 2-(aminomethyl)-3-o-tolylpyrrolo[1 ,2-7[1 .2,4]triazin-4(3H)-one (102 mg, 0.4 mmol), <strong>[62150-46-3]4-bromopicolinamide</strong> (105 mg, 0.52 mmol) and DIEA (200 mu, 1 .13 mmol) in n- butanol (2.2 mL) was reacted under microwave irradiation at 190C during 22 h. After cooled to room temperature, the mixture was concentrated in vacuum and was purified by reverse phase chromatography (C-18 silica from Waters, water/1 :1 acetonitrile- methanol as eluents [0.1 % v/v formic acid buffered] 0% to 100%) to obtain 7 mg of the title compound (4,6%).LRMS (m/z): 375 (M+1 )+.1H NMR (400 MHz, DMSO) delta 8.38 (s, 2 H), 8.01 (d, J=5.86 Hz, 1 H), 7.90 (m, 1 H), 7.61 - 7.73 (m, 1 H), 7.48 - 7.58 (m, 1 H), 7.39 - 7.48 (m, 1 H), 7.23 - 7.40 (m, 2 H), 7.03 - 7.14 (m, 1 H), 6.93 - 7.04 (m, 1 H), 6.62 (dd, J=4.30, 2.74 Hz, 1 H), 6.38 - 6.53 (m, 1 H), 3.86 - 3.99 (m, 2 H), 2.08 (s, 3 H)
4.6% With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 190℃; for 22h;Microwave irradiation; EXAMPLE 6 4-((4-Oxo-3-o-tolyl-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)methylamino)picolinamide A mixture of 2-(aminomethyl)-3-o-tolylpyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (102 mg, 04 mmol), <strong>[62150-46-3]4-bromopicolinamide</strong> (105 mg, 0,52 mmol) and DIEA (200 muL, 1,13 mmol) in n-butanol (2,2 mL) was reacted under microwave irradiation at 190ºC during 22 h. After cooled to room temperature, the mixture was concentrated in vacuo and was purified by reverse phase chromatography (C-18 silica from Waters, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to obtain 7 mg of the title compound (4,6%). LRMS (m/z): 375 (M+1)+. 1H NMR (400 MHz, dmso) delta 8.38 (s, 2 H), 8.01 (d, J=5.86 Hz, 1 H), 7.90 (m, 1 H), 7.61 - 7.73 (m, 1 H), 7.48 - 7.58 (m, 1 H), 7.39 - 7.48 (m, 1 H), 7.23 - 7.40 (m, 2 H), 7.03 - 7.14 (m, 1 H), 6.93 - 7.04 (m, 1 H), 6.62 (dd, J=4.30, 2.74 Hz, 1 H), 6.38 - 6.53 (m, 1 H), 3.86 - 3.99 (m, 2 H), 2.08 (s, 3 H)
  • 9
  • [ 1352152-51-2 ]
  • [ 62150-46-3 ]
  • [ 1352152-52-3 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; acetonitrile; at 90℃; for 4h;Inert atmosphere; (ii) (S)-tert- uty l-(2-(4-(2-carbamoylpyridin-4-yl)phcyanoethylcarbamoyl)cyclohexylcarbamateA solution of (S)-tert-butyl l-(l-cyano-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (Example 23 step (i),569 mg), potassium acetate (225 mg) and <strong>[62150-46-3]4-bromopicolinamide</strong> (230 mg) in mixture of acetonitrile (15 mL) and water (5 mL), was stirred under an atmosphere of nitrogen. 1,1¾z5(di-fert-butylphosphino)ferrocene palladium dichloride (22 mg) was added and the mixture heated at 90 C for 4h. The reaction mixture was concentrated to dryness and the residue purified on silica gel using ethyl acetate as eluant. Pure fractions were evaporated to dryness to afford the sub-titled compound (90 mg). m/e (APCI+) 490 [M-H]
  • 10
  • [ 1064578-14-8 ]
  • [ 62150-46-3 ]
  • 4-((2-(2-chlorophenyl)-8-methylquinolin-3-yl)methylamino)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 180℃; for 4h;Sealed tube; Microwave irradiation; The flask was charged with (2-(2-chlorophenyl)-8-methylquinolin-3-yl)methan- amine (100.0 mg, 0.354 mmol), obtained from A-1216 US PSP, procedure D, 4- bromopicolinamide (92 mg, 0.460 mmol), diisopropylethylamine (0.080 ml, 0.460 mmol) and 1-butanol (2.0 ml ) and sealed. The mixture was subjected to microwave at 180C for 4hrs. After cooled to room temperature, the mixture was concentrated, and the residue was diluted with MeOH. The solution was purified by HPLC, 25%-45% of B in 35min. The collected fractions were concentrated and dissolved in CH2Cl2, neutralized by washing with aq. NaHCO3. The CH2Cl2 layer was dried, concentrated and gave 4-((2-(2-chlorophenyl)-8-methylquinolin- 3-yl)methylamino)picolinamide, 1H-NMR (MeOD) delta 8.21 (s, 1 H), 8.01(d, J= 5.6 Hz, IH), 7.71 (d, J= 8.0 Hz, IH), 7.41-7.62 (m, 6 H), 7.20 (d, J= 2.4 Hz, IH), 6.50 (dd, J= 5.6,2.4 Hz, IH) 4.42 (d, J= 11.0 Hz, IH), 4.27 (d, J= 11.0 Hz, IH), 2.73 (s, 1 H). Mass Spectrum (ESI) m/e = 403.1 (M + 1).
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