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Chemical Structure| 157791-20-3 Chemical Structure| 157791-20-3

Structure of 157791-20-3

Chemical Structure| 157791-20-3

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Product Details of [ 157791-20-3 ]

CAS No. :157791-20-3
Formula : C6H13NO2
M.W : 131.17
SMILES Code : COC[C@@H]1CNCCO1
English Name :(2S)-2-(Methoxymethyl)morpholine
MDL No. :MFCD16294691

Safety of [ 157791-20-3 ]

Application In Synthesis of [ 157791-20-3 ]

* 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 [ 157791-20-3 ]

[ 157791-20-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1195782-58-1 ]
  • [ 157791-20-3 ]
  • [ 1195780-41-6 ]
YieldReaction ConditionsOperation in experiment
44.3% With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide 7H-Indolo[2,1-a][2]benzazepine-10-carboxamide, 6-[1-cyclobutyl-4-[[(2S)-2-(methoxymethyl)-4-morpholinyl]carbonyl-3-methyl]-1H-pyrazol-5-yl]-13-cyclohexyl-3-methoxy-N-[(1-methylethyl)sulfonyl]- A 2 dram vial was charged with 1H-pyrazole-4-carboxylic acid-5-methyl, 1-cyclobutyl-5-[13-cyclohexyl-3-methoxy-10-[[[(1-methylethyl)sulfonyl]amino]carbonyl]-7H-indolo[2,1-a][2]benzazepin-6-yl]-(70 mg, 0.104 μmmol), DMF (1 mL), 4-methylmorpholine (0.023 mL, 0.209 mmol), (S)-2-(methoxymethyl)morpholine (16.43 mg, 0.125 mmol) and o-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU) (36.9 mg, 0.115 mmol). The rxn was stirred over night. The rxn was diluted with DCM, washed with 0.1 N HCl (aqueous) then brine, dried (MgSO4) and evaporated giving a yellow syrup. The syrup was dissolved in DCM, the solution was added to a Thompson silica gel cartridge and it was eluted with DCM/methanol (0% to 4%). The appropriate fractions (TLC) were combined and evaporated giving a light yellow solid. The solid was triturated in ether/hexane and filtered giving the product (37 mg, 0.046 mmol, 44.3% yield) as a creamy white powder. HPLC: 97.9% pure, 22.34 minutes. LCMS: 784.19 at 3.98 minutes. 1H NMR: (400 Mz, CD3OD) δ 1.20-1.24 (m, 3H), 1.34-1.42 (m, 2H), 1.47-1.48 (m, 6H), 1.53-1.54 (m, 3 h), 1.77-1.79 (m, 6H), 1.93-1.98 (m, 3H), 2.08 (s, 3H), 2.29 (s, 3H), 2.33-2.35 (m, 2 h), 2.48 (bs, 1H), 2.74 (bs, 1H), 2.80 (s, 3 h), 2.87 (s, 3H), 2.94 (s, 2H), 3.03 (s, 1H), 3.17 (bs, 1H), 3.23 (s, 2H), 3.34-3.38 (m, 2H), 3.46-3.47 (d, J=7 Hz, 1H), 3.84 (bs, 1H), 3.95 (s, 3H), 4.08-4.09 (m, 2H), 4.52-4.55 (m, 1H), 4.76-4.86 (m, 2H), 6.71-6.74 (m, 1H), 6.93 (s, 1H), 7.11-7.12 (d, J=7 Hz, 1H), 7.58-7.66 (m, 2H), 7.71-7.73 (m, 1H), 7.89-7.90 (m, 1H), & 10.78 (bs, 1H).
  • 2
  • [ 443-75-4 ]
  • [ 157791-20-3 ]
  • [ 2923344-41-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; 36 General procedures I for amide coupling exemplified here for the production of: 2-(6-fluoro-1 H-indol-3-yl) -N-phenyl acetamide (40-006) (Compound 10021) General procedure: The solution of 2-(6-fluoro-1 H-indol-3-yl) acetic acid (100 mg, 0.52 mmol), aniline (53.0 mg, 0.57 mmol), HATU (216.5 mg, 0.57 mmol) and Et3N (68.1 mg, 0.67 mmol) in DCM (8 mL) was stirred at room temperature for 16 hours. After then, the mixture was diluted with dichloromethane (30 mL), which was washed with HCI (15 mL, 1 .0 N) and brine (20 mL), dried over sodium sulfate. After filtration and concentration, the residue was purified by flash column on silica gel to obtain desired product as colorless oil (80 mg, 57.6% yield). MS (ESI+) m/z 269 (M+H)+. 1H NMR (400 MHz, DMSO-d6) 5 10.98 (s, 1 H), 10.09 (s, 1 H), 7.76 - 7.48 (m, 3H), 7.38 - 7.20 (m, 3H), 7.12 (dd, J = 10.2, 2.3 Hz, 1 H), 7.08 - 6.96 (m, 1 H), 6.88-6.83 (m, 1 H), 3.71 (s, 2H).
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; 36 General procedures I for amide coupling exemplified here for the production of: 2-(6-fluoro-1 H-indol-3-yl) -N-phenyl acetamide (40-006) (Compound 10021) General procedure: The solution of 2-(6-fluoro-1 H-indol-3-yl) acetic acid (100 mg, 0.52 mmol), aniline (53.0 mg, 0.57 mmol), HATU (216.5 mg, 0.57 mmol) and Et3N (68.1 mg, 0.67 mmol) in DCM (8 mL) was stirred at room temperature for 16 hours. After then, the mixture was diluted with dichloromethane (30 mL), which was washed with HCI (15 mL, 1 .0 N) and brine (20 mL), dried over sodium sulfate. After filtration and concentration, the residue was purified by flash column on silica gel to obtain desired product as colorless oil (80 mg, 57.6% yield). MS (ESI+) m/z 269 (M+H)+. 1H NMR (400 MHz, DMSO-d6) 5 10.98 (s, 1 H), 10.09 (s, 1 H), 7.76 - 7.48 (m, 3H), 7.38 - 7.20 (m, 3H), 7.12 (dd, J = 10.2, 2.3 Hz, 1 H), 7.08 - 6.96 (m, 1 H), 6.88-6.83 (m, 1 H), 3.71 (s, 2H).
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; 36 General procedures I for amide coupling exemplified here for the production of: 2-(6-fluoro-1 H-indol-3-yl) -N-phenyl acetamide (40-006) (Compound 10021) General procedure: The solution of 2-(6-fluoro-1 H-indol-3-yl) acetic acid (100 mg, 0.52 mmol), aniline (53.0 mg, 0.57 mmol), HATU (216.5 mg, 0.57 mmol) and Et3N (68.1 mg, 0.67 mmol) in DCM (8 mL) was stirred at room temperature for 16 hours. After then, the mixture was diluted with dichloromethane (30 mL), which was washed with HCI (15 mL, 1 .0 N) and brine (20 mL), dried over sodium sulfate. After filtration and concentration, the residue was purified by flash column on silica gel to obtain desired product as colorless oil (80 mg, 57.6% yield). MS (ESI+) m/z 269 (M+H)+. 1H NMR (400 MHz, DMSO-d6) 5 10.98 (s, 1 H), 10.09 (s, 1 H), 7.76 - 7.48 (m, 3H), 7.38 - 7.20 (m, 3H), 7.12 (dd, J = 10.2, 2.3 Hz, 1 H), 7.08 - 6.96 (m, 1 H), 6.88-6.83 (m, 1 H), 3.71 (s, 2H).
  • 3
  • [ 1632007-32-9 ]
  • [ 157791-20-3 ]
  • [ 3077494-19-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: (S)-2-(methoxymethyl)morpholine In N,N-dimethyl-formamide at 20℃; 6 Synthesis of Compound 11 Add compound B and DMF to the reaction flask, add 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), react at room temperature for 20 minutes, add compound 11a, react at room temperature overnight. Add water and ethyl acetate, stir and separate, wash the organic phase with water, distill under reduced pressure, and column chromatography (petroleum ether: ethyl acetate = 1:1, volume ratio) to obtain an off-white solid 11.
 

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