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[ CAS No. 134464-79-2 ] {[proInfo.proName]}

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Chemical Structure| 134464-79-2
Chemical Structure| 134464-79-2
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Product Details of [ 134464-79-2 ]

CAS No. :134464-79-2 MDL No. :MFCD10566037
Formula : C10H19NO2S Boiling Point : No data available
Linear Structure Formula :- InChI Key :USYCVFFWCMHPPG-UHFFFAOYSA-N
M.W : 217.33 Pubchem ID :21906090
Synonyms :

Safety of [ 134464-79-2 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 UN#:3077
Hazard Statements:H302-H319-H332-H372-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 134464-79-2 ]

* 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 [ 134464-79-2 ]

[ 134464-79-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 134464-79-2 ]
  • [ 165197-50-2 ]
  • [ 165197-36-4 ]
  • 2
  • [ 134464-79-2 ]
  • [ 165197-32-0 ]
  • [ 165197-33-1 ]
  • 3
  • C18H15FIN3O2*ClH [ No CAS ]
  • [ 134464-79-2 ]
  • 1,1-dimethylethyl 4-[(3-(aminocarbonyl)-4-[4-fluoro-3-(methyloxy)phenyl]amino}-8-methyl-6-quinolinyl)thio]-1-piperidinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); bis[2-(diphenylphosphino)phenyl] ether; In DMF (N,N-dimethyl-formamide); at 100℃; for 3h; To a solution of Intermediate 35 (1. 0g) in N,N-dimethylformamide (30ml) under an atmosphere of nitrogen was added 1, 1-DIMETHYLETHYL 4-MERCAPTO-1-PIPERIDINECARBOXYLATE (0. 89g, US5317025A), potassium tert-butoxide (0. 46g), tris (dibenzylideneacetone) DIPALLADIUM (0) (0. 19g) and (oxydi-2, 1-PHENYLENE) bis (diphenylphosphine) (0. 11g). The mixture was heated to 100C for 3h, cooled and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate (100ml) and water (100ML) then dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by SPE (eluting with a gradient of 0 to 5% methanol in chloroform) to give intermediate 1, 1-dimethylethyl 4-[(3-(aminocarbonyl)-4-[4-fluoro-3-(methyloxy)phenyl] AMINO}-8-METHYL-6-QUINOLINYL) THIO]-1-PIPERIDINECARBOXYLATE as a yellow solid (1. 1g). This sulphide was dissolved in N,N-dimethylformamide (50ml) and oxone (5. 15g) was added portionwise. The mixture was stirred at room temperature for 3h, then quenched by addition of 1 M sodium sulphite solution (500ml). The mixture was extracted with chloroform (2 x 200MOI), and the organic layers were washed with 10% lithium chloride solution, dried over magnesium sulphate, filtered and concentrated to give the title compound as a pale yellow solid (0. 71G) AFTER trituration with ether. LC/MS Rt 3. 04 min, M/Z 573 [MH+]
  • 4
  • C19H16IN5O*ClH [ No CAS ]
  • [ 134464-79-2 ]
  • 1,1-dimethylethyl 4-({3-(aminocarbonyl)-8-methyl-4-[(1-methyl-1H-benzimidazol-6-yl)amino]-6-quinolinyl}thio)-1-piperidinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); bis[2-(diphenylphosphino)phenyl] ether; In DMF (N,N-dimethyl-formamide); at 100℃; for 2h; A mixture containing Intermediate 44 (0. 500g), 1, 1-dimethylethyl 4-mercapto-1- piperidinecarboxylate (0. 442g, synthesised according to US5317025A), potassium tert- butoxide (0. 248g), tris (DIBENZYLIDENEACETONE) DIPALLADIUM (0. 093g) and (oxydi-2, 1- phenylen) bis (diphenylphosphine) (0. 091g) was dissolved in N, N-DIMETHYLFORMAMIDE (20ml) and stirred under an atmosphere of nitrogen at 100C for 2h. The solvents were concentrated in vacuo and the residue partitioned between ethyl acetate (100MOI) and water (100MOI). The organic extract was washed with sodium bicarbonate solution followed by brine, dried over magnesium sulfate and concentrated in vacuo to an orange solid. This was purified by flash chromatography on silica gel eluting with a gradient of ethanol (0% to 10%) in ethyl acetate, to give the intermediate sulphide 1, 1-dimethylethyl 4-({3-(AMINOCARBONYL)-8-METHYL-4-[(1-METHYL-1 H-BENZIMIDAZOL-6-YL) amino]-6- QUINOLINYL} thio)-1-piperidinecarboxylate as a yellow solid (0. 375g). LC/MS Rt 2. 63 min, M/Z 547 [MH+] Oxone (1. 6g) was added to a solution of the sulphide (0. 370g) in N, N-dimethylformamide (10ML). The mixture was stirred at room temperature for 1h and was quenched with a solution of sodium sulphite (4g) in water (150ml). The mixture was extracted with ethyl acetate (2 x 100ML) and the combined organic suspension washed with water (2 x 100MOL) and extracted in vacuo to a pale yellow solid. This was purified by recrystallisation from boiling methanol to give the title compound as a pale yellow powder (0. 265g). LC/MS Rt 2. 47 MIN,/7 579 [MH+]
  • 5
  • [ 832714-08-6 ]
  • [ 134464-79-2 ]
  • [ 832716-87-7 ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 1h; 4-CHLORO-1-(4-METHANESULFONYL-PHENYL)-LH-PYRAZOLO [3, 4-d] pyrimidine (1. 23 mmol, 250 mg), 4- MERCAPTO-PIPERIDINE-1-CARBOXYLIC acid tert-butyl ester (1. 23 mmol, 268 mg) and potassium carbonate (1. 4 mmol, 203 mg) were dissolved in DMF (10 ML) and stirred for 60 minutes at room temperature. Its progress was followed by thin layer chromatography and LCMS. The reaction mixture was quenched with water followed by an extraction with ethylacetate. Removal of organic solvents in vacuo and purification by column chromatography provided compound A102 as a white solid (264 mg, 66%) O TH NMR (400 MHz, CDC13) B (ppm) : 8. 83 (s, 1H) ; 8. 61 (d, 2H) ; 8. 24 (s, 1H) ; 8. 11 (d, 2H) ; 4. 42 (h, 1H) ; 4. 00 (M, 2H) ; 3. 20 (m, 2H) ; 3. 15 (s, 3H) ; 2. 19 (M, 2H) ; 1. 77 (M, 2H) ; 1. 46 (s, 9H).. LCMS (ESI), M/Z 490. 3 (MH+, 100%)
  • 6
  • [ 832717-29-0 ]
  • [ 134464-79-2 ]
  • 4-[3-(4-methanesulfonyl-phenyl)-isoxazolo[4,5-d]pyrimidin-7-ylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 1.5h; 7-CHLORO-3- (4-METHANESULFONYL-PHENYL)-ISOXAZOLO [4, 5-d] pyrimidine (0. 19 mmol, 60 mg), 4- MERCAPTO-PIPERIDINE-1-CARBOXYLIC acid tert-butyl ester (0. 25 mmol, 54 mg) and potassium carbonate (0. 28 mmol, 35 mg) were dissolved in DMF (10 mL) and stirred for 90 minutes at room temperature. Its progress was monitored by thin layer chromatography and LCMS. The reaction was treated with water and the desired compound was extracted with ethyl acetate. The organic layer was evaporated in vacuo. Purification by HPLC provided compound D3 as a white solid (40 mg, 35%). H NMR (400MZ, CDCl3) 8 9. 03 (s, 1H) ; 8. 71 (d, 2H) ; 8. 15 (d, 2H) ; 4. 44 (h, 1H) ; 4. 02 (M, 2H) ; 3. 22 (M, 2H) ; 3. 13 (s, 3H) ; 2. 19 (M, 2H) ; 1. 82 (M, 2H) ; 1. 47 (s, 9H). LCMS (ESI), M/Z 491. 1 (MH+, 100%)
  • 7
  • [ 4316-97-6 ]
  • [ 134464-79-2 ]
  • [ 832755-10-9 ]
YieldReaction ConditionsOperation in experiment
97% With sodium t-butanolate; In tetrahydrofuran; for 0.0833333h; A mixture OF 4-MERCAPTO-PIPERIDINE-1-CARBOXYLIC acid TERT-BUTYL ester (1.5352 g, 7.06 mmol) and 4,6-dichloro-5-methyl-pyrimidine (1.1512 g, 7.06 mmol) in 15 mL of THF with sodium t- butoxide (1M in THF, 8.3 mL, 8.3 mmol) added dropwise. After 5 min, mixture was concentrated and residue was extracted with CH2C12 and H20. Organic phase was dried over MGS04, filtered and concentrated to give 4- (6-CHLORO-5-METHYL-PYRIMIDIN-4-YLSULFANYL)-PIPERIDINE-1-CARBOXYLIC acid TERT- butyl ester as a yellowish solid (2.3469 g, 97%). Exact mass calculated for CL5H22CIN302S 343.11, found 344.1 (MH+).
  • 8
  • [ 857653-95-3 ]
  • [ 134464-79-2 ]
  • 4-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tetrahydrofuran; for 1.66667h; Example 131: 4- (3-Pyridin-4-yl- [1, 2,4] oxadiazol-5-ylmethylsulfanyl) piperidine-1-carboxylic acid tert-butyl ester t-BuOK (92mg, 83μmol) and methanesulfonic acid 3-pyridin-4-yl- [1, 2,4] oxadiazol-5- ylmethyl ester (Preparation 12,150mg, 588μmol) were added to a stirred solution of 4- mercaptopiperidine-l-carboxylic acid tert-butyl ester (191mg, 881μmol) in anhydrous THF (lOml). After 10min, the reaction mixture was diluted with Et2O, before being washed with NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, and concentrated, then the residue was purified by column chromatography (IH-EtOAc, 3: 2) to afford the title compound: RT = 3. 77min ; mlz (ES) = 377.2 [M+H] +.
  • 9
  • [ 134464-79-2 ]
  • 4-(furo[3,2-c]pyridine-2-carbonylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 1; 4-(Furo[3,2-c]pyridine-2-carbonylsulfanyl)piperidine-l-carboxylic acid tert-mγ ester; A solution of EDCI (66 mg, 0.35 mmol) in anhydrous DMF (2 mL) was added to a stirred solution of furo[3,2-c]pyridine-2-carboxylic acid (45 mg, 0.28 mmol) in anhydrous DMF (1 mL). After 1 h, the mixture was treated with a solution of DMAP (6 mg, 0.05 mmol) and 4- mercaptopiperidine-1-carboxylic acid tert-butyl ester (50 mg, 0.23 mmol), before being stirred for an additional 16 h. The DMF was removed under reduced pressure, then the residue was purified by flash chromatography (IH-EtOAc, 1:1 to 3:7) to furnish the title compound
  • 10
  • [ 365532-34-9 ]
  • [ 134464-79-2 ]
  • 2-Oxo-3-{ [1-(tert-butyloxycarbonyl)-piperidin-4-yl]sulfanyl}-tetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In N,N-dimethyl-formamide; EXAMPLE XV 1-(tert-butyloxycarbonyl)-4-[(2-oxotetrahydrofuran-3-yl)sulfanyl]piperidine 2.73 g of potassium tert-butoxide is slowly added to 5.28 g of 1-(tert-butyloxycarbonyl)-4-mercaptopiperidine in 20 ml of N,N-dimethylformamide while cooling with an ice bath. The mixture is stirred for another 30 minutes while cooling with an ice bath, then a solution of 2.02 ml of 3-bromodihydrofuran-2-one in 20 ml of N,N-dimethylformamide is added dropwise. After the addition has finished, the reaction mixture is stirred for two hours at ambient temperature. It is then neutralized with glacial acetic acid and concentrated by evaporation. The residue is divided between ethyl acetate and water. The organic phase is dried over magnesium sulfate and concentrated by evaporation. 7.60 g of a brownish-orange oil remain, which is reacted without further purification. Rf value: 0.32 (silica gel, ethyl acetate/cyclohexane=2:3) mass spectrum (ESI-): m/z=300 [M-H]-
potassium tert-butylate; In N,N-dimethyl-formamide; EXAMPLE XIX 2-Oxo-3-{ [1-(tert.-butyloxycarbonyl)-piperidin-4-yl]sulfanyl}-tetrahydrofuran The compound is obtained by reaction of 1-(tert.-butyloxycarbonyl)-4-mercapto-piperidine with 3-bromo-dihydro-furan-2-one in N,N-dimethylformamide in the presence of potassium tert.butylate. Rf value: 0.35 (siica gel, cyclohexane/ethyl acetate=3:2) Mass spectrum (ESI-): m/z=300 [M-H]-
  • 11
  • sodium methoxide-methanol [ No CAS ]
  • [ 141699-66-3 ]
  • [ 134464-79-2 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In methanol; Reference Example 12 1-(tert-Butoxycarbonyl)-4-mercaptopiperidine STR254 In dry methanol were dissolved 520 mg (2 mmol) of 4-(acetylthio)-1-(tert-butoxycarbonyl)piperidine, and 420 μl (2 mmol) of a 28% sodium methoxide-methanol solution were added to the mixture under ice-cooling and under a nitrogen atmosphere, followed by stirring of the resulting mixture for 40 minutes. Then, 173 μl of acetic acid were added to the mixture and the solvent was distilled off at room temperature, followed by diluting of the residue with ethyl acetate. The mixture was washed successively with an aqueous sodium hydrogencarbonate solution and an aqueous NaCl solution in the order and the solvent was distilled off to obtain 430 mg of reddish orange oil. This product was used for a subsequent reaction without purification. NMR spectrum (270 MHz, CDCl3) δ ppm: 1.46 (9H, s), 1.5-1.6 (2H, m), 1.9-2.0 (2H, m), 2.8-3.0 (3H, m), 3.9-4.1 (2H, m). Mass spectrum m/e: 217, 202, 184, 161, 144, 127, 117, 84, 82.
  • 12
  • [ 929095-64-7 ]
  • [ 134464-79-2 ]
  • tert-butyl 4-[({1-[4-[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-(methoxycarbonyl)thien-2-yl]-1H-benzimidazol-6-yl}methyl)thio]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 14h; A mixture of methyl 5-[6-(chloromethyl)-1 Mbenzimidazol-1 -yl]-3-[(1 R)-λ -(2- chlorophenyl)ethyl]oxy}thiophene-2-carboxylate (0.843 g, 1.83 mmol), te/7- butyl 4-mercaptopiperidine-1-carboxylate (0.456 g, 2.10 mmol), and potassium carbonate (0.694 g, 5.02 mmol) in /V,/V-dimethylformamide (10 ml_) was stirred at 600C for 14 h. The reaction was cooled to room temperature and partitioned between ethyl acetate (100 ml_) and water (100 ml_). The layers were separated and the organic layer was washed with water (5 x 50 ml_), dried over sodium sulfate and concentrated in vacuo to afford 1.23 g(100%) of the title compound as a colorless solid. 1H NMR (400 MHz, DMSO- Cf6): δ 8.63 (s, 1H)1 7.74-7.69 (m, 2H), 7.60 (br s, 1H), 7.48-7.41 (m, 3H), 7.36- 7.32 (m, 2H), 5.96 (q, 1H, J= 6.2 Hz), 3.94 (br s, 2H), 3.82 (s, 3H), 3.80-3.73 (m, 2H), 2.88-2.70 (m, 3H), 1.91-1.82 (m, 2H), 1.62 (d, 3H, J= 6.2 Hz), 1.40- 1.25 (m, 2H), 1.36 (s, 9H).
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