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Chemical Structure| 190850-37-4 Chemical Structure| 190850-37-4

Structure of 190850-37-4

Chemical Structure| 190850-37-4

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Product Details of [ 190850-37-4 ]

CAS No. :190850-37-4
Formula : C12H8ClNO
M.W : 217.65
SMILES Code : O=C(Cl)C1=CC=C(C2=NC=CC=C2)C=C1
English Name :4-(Pyridin-2-yl)benzoyl chloride

Safety of [ 190850-37-4 ]

Application In Synthesis of [ 190850-37-4 ]

* 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 [ 190850-37-4 ]

[ 190850-37-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4385-62-0 ]
  • [ 190850-37-4 ]
YieldReaction ConditionsOperation in experiment
76% With thionyl chloride Reflux; 155.B Example 155 Bmethyl 2-hydroxy-3-(4-(pyridin-2-yl)benzamido)benzoate; Thionyl chloride (10 mL) was added to 4-(pyridin-2-yl)benzoic acid (1.8 g, 9 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum to give crude 4-(pyridin-2-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (1 g, 6 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) were added the crude 4-(pyridin-2-yl)benzoyl chloride (1.3 g, 6 mmol) portion wise at 0° C. and then stirred at 70° C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain yellow solid of methyl 2-hydroxy-3-(4-(pyridin-2-yl)benzamido)benzoate (1.6 g, yield 76%). LC-MS (ESI) m/z: 349 (M+1)+. (M+1)+.
With thionyl chloride
With thionyl chloride 2b; 4; 8 Example 4. Synthesis of 1,14-Di(methyl-d3) (3S,8S,9S,12S)-3,12-bis[(1,1-dimethylethyl)-d9]-8-hydroxy-4,1-dioxo-9-(phenylmethyl)-6-[[ 4-(2-pyridinyl)phenyl]methyl-d2]-2,5,6,14,13-pentaazatetradecanedioate (Compound 131). [Show Image] Compound 131 was prepared according to Scheme 1, above, following the General Method A described above- Deuterium gas (Cambridge Isotopes, 99.8 atom% D), MeOD (Aldrich, 99.5 atom% D), iPrOD (Aldrich, 98 atom% D) and deuterium chloride (Aldrich, 99 atom% D) were used in this synthesis. Deuferated aldehyde X was prepared according to Scheme 2b using LiAlD4 (Cambridge Isotopes, 98 atom% D). 1H-NMR (300 MHz, CDCl3): δ 2.71 (dd, 2H), 2.94 (d, 2H), 3.56 (d, 2H), 3.77 (d, 1H), 4.02-4.05 (m, 1H), 4.83 (s, 1H), 5.19-5.29 (m, 2H), 6.40-6.47 (m, 2H), 7.20-7.23 (m, 6H, partially obscured by CDCl3), 7.41 (d, 2H), 7.69-7.76 (m, 2H), 7.95 (d, 2H), 8.69 (d, 1H). HPLC (method: 20 mm C18-RP column - gradient method 2- 95% ACN + 0.1 % formic acid in 3.3 min with 1.7 min hold at 95% ACN; Wavelength: 254 nm): retention time: 3.22 min; purity: 99.2%. MS (M+H+): 731.7.; Example 8. Synthesis of 1,14-Dimethyl (3S,8S,9S,12S)-3,12-bis[(1,1-dimethylethyl)-d2]-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[ 4-(2-pyridinyl)phenyl]methyl-d2]-2,5,6,10-13-pentaazatetradecanedioate (Compound 113). [Show Image] Compound 113 was prepared according to Scheme 1, above, following the General Method A described above. Deuterium gas (Cambridge Isotopes, 99.8 atom% D), MeOD (Aldrich, 99.5 atom% D), iPrOD (Aldrich, 98 atom% D) and deuterium chloride (Aldrich, 99 atom% D) were used in this synthesis. Deuterated aldehyde X was prepared according to Scheme 2b using LiAlD4 (Cambridge Isotopes, 98 atom% D). 1H-NMR (300 MHz, CDCl3): δ 2.69 (dd, 2H), 2.94 (d, 2H), 3.56-3.59 (m, 2H), 3.64 (s, 3H), 3.67 (s, 3H), 3.77 (d, 1H), 4.02-4.05 (m, 1H), 4.84 (s, 1H), 5.18-5.32 (m, 2H), 6.40-6.45 (m, 2H), 7.14-7.26 (m, 6H, partially obscured by CDCl3), 7.41 (d, 2H), 7.61-7.80 (m, 2H), 7.95 (d, 2H), 8.69 (d, 1H). HPLC (method: 20 mm C18-RP column - gradient method 2-95% ACN + 0.1% formic acid in 3.3 min with 1.7 min hold at 95% ACN; Wavelength: 254 nm): retention time: 3.25 min; purity: 99.4%. MS (M+H+): 725.4.
With thionyl chloride for 5h; Heating / reflux; 1.d The biarylcarboxylic acids (0.00057 mol) were treated with 5 mL of SOCl2 for 5 h under reflux. The excess of SOCl2 was removed by distillation and the crude acid chloride was used in the next reaction without further purification.; d) N-{4-[4-(2, 4-Dimethoxy-phenyl)-piperazin-l-yl]-butyl}-4-(pyridin-2- yl)-benzamide Prepared by reaction with 4-(pyridin-2-yl)-benzoic acid according to the general procedure (acid chloride method). Yield: 35%. Mp 154.5-1560C (free base); 212-216°C (HCl salt) 1H-NMR (CDCl3) δ (ppm): 8.66 (d, IH); 8.02 (d, 2H); 7.85 (d, 2H); 7.75 (m, 2H); 7.23 (m, IH); 6.96 (br s, IH); 6.76 (d, IH); 6.42 (d, IH); 6.36 (dd, IH); 3.78 (s, 3H); 3.72 (s, 3H); 3.47 (m, 2H); 2.97 (m, 4H); 2.65 (m, 4H); 2.47 (t, 2H); 1.70 (m, 4H) Mass (ES) m/z %: 475 (M+ 1, 100%); 497 (M+Na, 19%) HPLC: column Zorbax C8 MeOH 80% / H2O 20%, 1.0 mL/min; Rt 6.54; area = 99%
With thionyl chloride for 12h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 4.58h;
With thionyl chloride for 1h; Heating / reflux; 1.B EXAMPLE 1B N-(4-tert-butylphenyl)-4-(2-pyridinyl)benzamide The product from Example 1A (570 mg, 2.86 mmol) in SOCl2 (10 mL) was refluxed for 1 hour. The solution was allowed to cool to room temperature and SOCl2 was removed under reduced pressure. The residue was taken up in tetrahydrofuran (10 mL) and treated with DIEA (2.5 mL, 14.4 mmol, 5 eq) and 4tert-butylaniline (0.41 mL, 2.57 mmol). After stirring overnight at room temperature, the tetrahydrofuran was removed under reduced pressure and replaced with ethyl acetate (20 mL). The ethyl acetate was washed with H2O and brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on silica gel (eluant gradient from 7:3 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.71-8.74 (m, 1H), 8.23-8.26 (m, 2H), 8.07-8.10 (m, 3H), 7.94 (td, J=7.4 Hz, 2.1 Hz, 1H), 7.70-7.73 (m, 2H), 7.37-7.44 (m, 3H), 1.29 (s, 9H); MS (ESI+) m/z 331 (M+H)+.
With thionyl chloride at 85℃; for 10h;

  • 2
  • [ 2041-15-8 ]
  • [ 190850-37-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine In dichloromethane for 12h; Reflux; L400 Example L400 28 ml of triethylamine and then, dropwise, a solution of 21.8 g [100 mmol) of 4-(2-pyridinyl)benzoyl chloride [190850-37-4] in 100 ml of dichloromethane are added to a vigourously stirred solution of 4.0 g (30 mmol) of cis,cis-1,3,5-cyclohexanetriol [50409-12-6] in 100 ml of dichloromethane, and the mixture is stirred under reflux for 12 h. After cooling, the volatile constituents are removed in vacuo, the residue is washed by stirring with 300 ml of hot methanol, the product is filtered off with suction, washed three times with 50 ml of methanol each time and finally recrystallised from ethyl acetate/methanol. Yield: 14.0 g (21 mmol), 69%. Purity: about 97% according to 1H-NMR
 

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