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[ CAS No. 40137-11-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 40137-11-9
Chemical Structure| 40137-11-9
Chemical Structure| 40137-11-9
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Product Details of [ 40137-11-9 ]

CAS No. :40137-11-9 MDL No. :MFCD00181919
Formula : C6H15O5PS Boiling Point : -
Linear Structure Formula :- InChI Key :DFCKGLGTOXDULU-UHFFFAOYSA-N
M.W : 230.22 Pubchem ID :533797
Synonyms :

Safety of [ 40137-11-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 40137-11-9 ]

* 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 [ 40137-11-9 ]

[ 40137-11-9 ] Synthesis Path-Downstream   1~94

  • 1
  • [ 1144-74-7 ]
  • [ 40137-11-9 ]
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  • [ 40137-11-9 ]
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  • 4
  • [ 110-52-1 ]
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  • [ 14371-10-9 ]
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  • 6
  • [ 14371-10-9 ]
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  • 7
  • [ 487-89-8 ]
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  • 9
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  • 10
  • [ 123-73-9 ]
  • [ 40137-11-9 ]
  • (1E,3E)-1-Methanesulfonyl-penta-1,3-diene [ No CAS ]
  • 11
  • [ 78-85-3 ]
  • [ 40137-11-9 ]
  • (E)-1-Methanesulfonyl-3-methyl-buta-1,3-diene [ No CAS ]
  • 12
  • [ 930-68-7 ]
  • [ 40137-11-9 ]
  • 3-[1-Methanesulfonyl-meth-(Z)-ylidene]-cyclohexene [ No CAS ]
  • 3-[1-Methanesulfonyl-meth-(E)-ylidene]-cyclohexene [ No CAS ]
  • 13
  • [ 591-50-4 ]
  • [ 40137-11-9 ]
  • Diethyl <α-phenyl-α-(methanesulfonyl)methyl>phosphonate [ No CAS ]
  • 14
  • [ 110-43-0 ]
  • [ 40137-11-9 ]
  • [ 35378-30-4 ]
  • 15
  • [ 705-60-2 ]
  • [ 40137-11-9 ]
  • Diethyl 5-methanesulfonyl-3-methyl-4-phenyl-2-isoxazoline-5-ylphosphonate [ No CAS ]
  • 16
  • [ 5392-12-1 ]
  • [ 40137-11-9 ]
  • [ 76041-83-3 ]
  • 17
  • [ 20452-67-9 ]
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  • 18
  • [ 40137-11-9 ]
  • [ 619-22-7 ]
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  • 19
  • [ 40137-11-9 ]
  • [ 39119-83-0 ]
  • Diethyl α-(2-formylphenyl)-α-(methanesulfonyl)methylphosphonate [ No CAS ]
  • 20
  • [ 40137-11-9 ]
  • [ 108-94-1 ]
  • [ 35378-31-5 ]
  • 21
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  • [ 104-87-0 ]
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  • 22
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  • 23
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  • [ 104-88-1 ]
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  • 24
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  • [ 99-61-6 ]
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  • 25
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  • [ 555-16-8 ]
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  • 26
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  • [ 100-52-7 ]
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  • 27
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  • 28
  • [ 122422-71-3 ]
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  • 29
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  • [ 589-92-4 ]
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  • 30
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  • 31
  • [ 40137-11-9 ]
  • [ 3156-07-8 ]
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  • 32
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  • [ 525-06-4 ]
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  • 33
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  • [ 106-93-4 ]
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  • 34
  • [ 40137-11-9 ]
  • [ 78-84-2 ]
  • [ 5897-46-1 ]
  • (Z)-1-Methanesulfonyl-3-methyl-but-1-ene [ No CAS ]
  • [ 286376-75-8 ]
  • 35
  • [ 40137-11-9 ]
  • [ 120-92-3 ]
  • [ 74267-47-3 ]
  • 36
  • [ 40137-11-9 ]
  • [ 98-86-2 ]
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  • 37
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  • [ 105-07-7 ]
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  • 40
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  • 41
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  • 42
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  • 43
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  • [ 502-42-1 ]
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  • 44
  • [ 1122-54-9 ]
  • [ 40137-11-9 ]
  • [ 68063-80-9 ]
  • 4-(1-Methanesulfonylmethyl-vinyl)-pyridine [ No CAS ]
  • 4-((Z)-2-Methanesulfonyl-1-methyl-vinyl)-pyridine [ No CAS ]
  • 45
  • [ 350-03-8 ]
  • [ 40137-11-9 ]
  • [ 68063-79-6 ]
  • 3-(1-Methanesulfonylmethyl-vinyl)-pyridine [ No CAS ]
  • 3-((Z)-2-Methanesulfonyl-1-methyl-vinyl)-pyridine [ No CAS ]
  • 46
  • [ 1122-62-9 ]
  • [ 40137-11-9 ]
  • 2-((Z)-2-Methanesulfonyl-1-methyl-vinyl)-pyridine [ No CAS ]
  • 2-((E)-2-Methanesulfonyl-1-methyl-vinyl)-pyridine [ No CAS ]
  • 47
  • [ 894853-74-8 ]
  • [ 40137-11-9 ]
  • [ 894853-81-7 ]
  • 49
  • [ 40137-11-9 ]
  • endo-3-succinimido-4-diethylphosphono-4-methylsulfonyl-1-cyclohexene [ No CAS ]
  • 50
  • [ 40137-11-9 ]
  • exo-3-succinimido-4-diethylphosphono-4-methylsulfonyl-1-cyclohexene [ No CAS ]
  • 53
  • [ 40137-11-9 ]
  • Diethyl 3-methyl-4-phenylisoxazole-5-ylphosphonate [ No CAS ]
  • 54
  • [ 40137-11-9 ]
  • [ 140182-19-0 ]
  • 56
  • [ 87762-57-0 ]
  • [ 40137-11-9 ]
  • 57
  • [ 40137-11-9 ]
  • [ 86448-48-8 ]
  • 58
  • diphenylmethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-2-oxoacetate [ No CAS ]
  • [ 40137-11-9 ]
  • Diphenylmethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-3-methylsulphonyl propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% EXAMPLE 8 Diphenylmethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-3-methylsulphonyl propenoate STR26 8.8 g of diethyl methylsulphonylmethyl phosphonate are reacted with 18 g of diphenylmethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-2-oxoacetate, analogously to Example 2. 9.2 g of the polar isomer are seperated off from the crude product by crystallization with ether. After the mother liquor has been evaporated down, 11.2 g of the slightly contaminated non-polar isomer remain as a viscous oil. Yield 95%.
  • 59
  • 2-trimethylsilyl ethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-2-oxoacetate [ No CAS ]
  • [ 40137-11-9 ]
  • 2-Trimethylsilylethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-3-methylsulphonyl propenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; EXAMPLE 2 2-Trimethylsilylethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-3-methylsulphonyl propenoate STR20 55.94 ml of a 1.5M solution of n-butyl-lithium in hexane are added dropwise to a solution of 8.64 ml of diisopropylamine in 120 ml of absolute tetrahydrofuran at -70, under nitrogen, in a heated flask. After 15 minutes, 17.3 g of diethyl methylsulphonylmethyl phosphonate are added, and after a further 15 minutes a solution of 30 g of 2-trimethylsilyl ethyl 2-(2-tert.-butoxycarbonylaminothiazol-4-yl)-2-oxoacetate in 50 ml of absolute tetrahydrofuran is added dropwise. The reaction mixture is kept at -40 for one hour, and is then thawed at room temperature and stirred further overnight. Working up as in Example 1 gives 40.3 g of crude product, which is processed further without purification. According to thin layer chromatography/NMR, one isomer is formed in excess. NMR (CDCl3): delta=7.16(1)s, 7.12(1)s, 4.45(2)m, 3.10(3)s, Principal product 1.52(9)s, 1.22(2)m, 0.03(9)s ppm.
  • 60
  • aldehyde tBoc-Val-Ala-Leu-CHO [ No CAS ]
  • (S)-(E)-3-((tert-butoxycarbonylamino-valyl)alanyl)amino-methylsulfonyl-5-methyl-1-hexene [ No CAS ]
  • [ 40137-11-9 ]
  • (S)-(E)-3-((tert-butoxycarbonylaminovalyl)alanyl)amino-1-methylsulfonyl-5-methyl-1-hexene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; Preparation of (S)-(E)-3-((tert-butoxycarbonylaminovalyl)alanyl)amino-1-methylsulfonyl-5-methyl-1-hexene Diethyl methylsulfonylmethylphosphonate (30 mg, 130 mmol) was dissolved in dry THF (5 ml) and then cooled to 0C under an atmosphere of nitrogen. Sodium hydride (7 mg of 60% dispersion in oil, 175 mmol) was added and the mixture stirred for 15 mins (effervescence). The aldehyde tBoc-Val-Ala-Leu-CHO (50 mg, 129 mmol) was then added to the resulting solution and the mixture then stirred for 60 mins. The reaction was quenched by addition of dilute hydrochloric acid (0.1 M), followed by extraction with ethyl acetate(x3). The separated organic phase was sequentially washed with saturated sodium bicarbonate solution and.brine before drying over sodium sulphate. The volatiles were then removed in vacuo. The residue was purified by flash chromatography on silica eluding with ethyl acetate/hexane 8/2. An unidentified by-product was eluted first (4 mg), followed by the desired product (S)-(E)-3-((tert-butoxycarbonylamino-valyl)alanyl)amino-methylsulfonyl-5-methyl-1-hexene (24 mg, 40%) as a solid. MS (electrospray) required (M+(C21H39O6N3S)+1) =462: found (M++Na) =484, ((M-t Boc)+1)=362 (100%).
  • 61
  • (4S,4aS,10bS)-10b-((4-chlorophenyl)sulfonyl)-7,10-difluoro-1,2,4,4a,5,10b-hexahydropyrano[3,4-c]chromene-4-carbaldehyde [ No CAS ]
  • [ 40137-11-9 ]
  • C21H19ClF2O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 2To a solution of 34.5 g (150 mmol) of diethyl methylsulfonomethyl-phosphonate [ref:G. H. Posner and D. J. Brunelle J. Org. Chem. 1972, 37, 3547] in 500 mL of THF was added 145 mL (145 mmol) of LiHMDS in THF at -78 0C. After 40 min., a solution of 31.5 g (73.5 mmol) of the aldehyde 32 in 60 mL of THF was added, and the mixture was stirred at -78 0C for 5h. It was quenched with 200 mL of saturated aqueous NH4CI and 500 mL of water, and extracted with four 500 mL portions of ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to give crude vinyl sulfone 33-rac. MS: Calcd for C21H20CIF2OeS2 (M+1 )+ m/z = 505.0, found 505, Rt = 4.20 min.
  • 63
  • [ 40137-11-9 ]
  • [ 222639-45-4 ]
  • [ 1190853-19-0 ]
  • 64
  • [ 40137-11-9 ]
  • [ 170112-07-9 ]
  • C17H25NO4S [ No CAS ]
  • 65
  • [ 40137-11-9 ]
  • [ 1246261-47-1 ]
  • [ 1246261-57-3 ]
  • 66
  • [ 40137-11-9 ]
  • [ 1246261-48-2 ]
  • [ 1246261-58-4 ]
  • 67
  • [ 40137-11-9 ]
  • [ 1246261-49-3 ]
  • [ 1246261-59-5 ]
  • 68
  • [ 40137-11-9 ]
  • [ 1246261-50-6 ]
  • [ 1246261-61-9 ]
  • 69
  • [ 40137-11-9 ]
  • [ 98482-70-3 ]
  • [ 1246261-52-8 ]
  • 70
  • [ 40137-11-9 ]
  • [ 1241914-71-5 ]
  • [ 1241916-14-2 ]
YieldReaction ConditionsOperation in experiment
[00431] Step B: To <strong>[40137-11-9]diethyl methylsulfonylmethylphosphonate</strong> (746 mg, 3.24 mmol) in THF (20 mL) at 0 0C was added potassium ?-butoxide (1.0 M in THF, 3.25 mL, 3.25 mmol) and the mixture was stirred for 5 min. Then (4-fluorophenyl)(4-(5- methyl-lH-pyrazol-3-ylamino)quinazolin-2-yl)methanone from Example 3 (375 mg, 1.08 mmol) was added and the mixture was stirred at rt for 4 h. The mixture was treated with 1 N HCl and the resulting mixture was extracted with EtOAc. The organic layer was washed with brine and then concentrated to a residue (700 mg), which was subjected to silica gel chromatography eluting with 1-10% MeOH/DCM to give impure material. To a portion of this material (166 mg) in EtOAc (5 mL) was added 10% Pd-C (166 mg) and the mixture was stirred under a hydrogen atmosphere at rt overnight. The mixture was filtered and to the filtrate was added palladium on carbon (10%). The mixture was stirred under a hydrogen atmosphere for several hours, and then filtered. The filtrate was concentrated to a solid, which was triturated with ether to afford 2-(l-(4-fluorophenyl)-2-(methylsulfonyl)ethyl)-N-(5-methyl-lH- pyrazol-3-yl)quinazolin-4-amine (22 mg). 1H NMR (300 MHz, DMSO-J6) delta 2.28 (s, 3 H) 2.87 (s, 3H) 3.85 (m, IH) 4.34 (m, IH) 4.68 (bs, IH) 6.45 (s, IH) 7.15 (t, 2H) 7.49 (m, 3H) 7.76 (m, 2H) 8.56 (d, IH) 10.36 (s, IH) 12.17 (s, IH); LC-MS (ESI) m/z 426 (M + H) +.
With hydrogenchloride; potassium tert-butylate;Pd-C; palladium; In tetrahydrofuran; ethyl acetate; Step B: To <strong>[40137-11-9]diethyl methylsulfonylmethylphosphonate</strong> (746 mg, 3.24 mmol) in THF (20 mL) at 0 C. was added potassium t-butoxide (1.0 M in THF, 3.25 mL, 3.25 mmol) and the mixture was stirred for 5 min. Then (4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone from Example 3 (375 mg, 1.08 mmol) was added and the mixture was stirred at room temperature for 4 hrs. The mixture was treated with 1 N HCl and the resulting mixture was extracted with EtOAc. The organic layer was washed with brine and then concentrated to a residue (700 mg), which was subjected to silica gel chromatography eluting with 1-10% MeOH/DCM to give impure material. To a portion of this material (166 mg) in EtOAc (5 mL) was added 10% Pd-C (166 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. The mixture was filtered and to the filtrate was added palladium on carbon (10%). The mixture was stirred under a hydrogen atmosphere for several hours, and then filtered. The filtrate was concentrated to a solid, which was triturated with ether to afford 2-(1-(4-fluorophenyl)-2-(methylsulfonyl)ethyl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine (22 mg). 1H NMR (300 MHz, DMSO-d6) delta2.28 (s, 3H) 2.87 (s, 3H) 3.85 (m, 1H) 4.34 (m, 1H) 4.68 (bs, 1H) 6.45 (s, 1H) 7.15 (t, 2H) 7.49 (m, 3H) 7.76 (m, 2H) 8.56 (d, 1H) 10.36 (s, 1H) 12.17 (s, 1H); LC-MS (ESI) m/z 426 (M+H)+.
  • 71
  • [ 40137-11-9 ]
  • [ 65564-05-8 ]
  • [ 1245941-14-3 ]
  • 72
  • [ 914672-79-0 ]
  • [ 40137-11-9 ]
  • C25H25FN2O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
step 1-To a solution of <strong>[40137-11-9]diethyl methylsulfonylmethylphosphonate</strong> (0.098 g, 0.43 mmol) and THF was added NaH (0.034 g, 0.85 mmol, 60% in mineral oil) and the reaction was stirred at RT for 20 min. The aldehyde 61a (0.13 g, 0.28 mmol) was added and the reaction stirred for 1 h at which time the LCMS shows mostly vinyl sulfone. The reaction was poured into water containing HCl (1 mL). The organics were immediately extracted with EtOAc, washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting a gradient of 1:1 EtOAc/hexane to 5% EtOAc/DCM containing 0.7% HOAc to afford 61b. The product thus obtained was used directly in step 2.
  • 73
  • [ 40137-11-9 ]
  • [ 1310711-23-9 ]
  • [ 1310711-25-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a suspension of NaH 60% (1.8 mmol, 1.1 equiv) in THF (5 ml), at 0 C, was added 1 equiv of the appropriate phosphonate. The resulting solution was stirred at temperature room for 30 min. A solution of 1 equiv of the appropriate aldehyde 3 in THF (16 ml) was added and stirred at room temperature for 2 h. The solvent was removed under reduced pressure, and the residue was dissolved in CH2Cl2. The organic solution was washed with brine, dried, and concentrated. The resulting residue was flash chromatographed.
  • 74
  • [ 40137-11-9 ]
  • [ 1310711-24-0 ]
  • [ 1310711-27-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a suspension of NaH 60% (1.8 mmol, 1.1 equiv) in THF (5 ml), at 0 C, was added 1 equiv of the appropriate phosphonate. The resulting solution was stirred at temperature room for 30 min. A solution of 1 equiv of the appropriate aldehyde 3 in THF (16 ml) was added and stirred at room temperature for 2 h. The solvent was removed under reduced pressure, and the residue was dissolved in CH2Cl2. The organic solution was washed with brine, dried, and concentrated. The resulting residue was flash chromatographed.
  • 75
  • <i>N</i>-(2-diethylamino-ethyl)-<i>N</i>'-[1-(1-formyl-3-methyl-butylcarbamoyl)-2-phenyl-ethyl]-terephthalamide [ No CAS ]
  • [ 40137-11-9 ]
  • [ 1346804-64-5 ]
YieldReaction ConditionsOperation in experiment
25% General procedure: A solution of 19 (482 mg, 2.09 mmol, 1.5 eq) in dry tetrahydrofuran (10 mL) was added at -70 C under nitrogen to a solution of sodium hydride 60% in mineral oil (83.6 mg, 2.09 mmol, 1.5 eq) in dry tetrahydrofuran (10 mL). After 30 min at -70 C, a solution of 20 (710 mg, 1.39 mmol, 1 eq) in dry tetrahydrofuran (10 mL) was added to the mixture. After return back to room temperature, the reaction was quenched with methanol (4 mL). The reaction mixture was evaporated under vacuum, then diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic layer was washed with aqueous saturated sodium bicarbonate solution (100 mL), dried with magnesium sulphate, filtered and evaporated under vacuum. The crude product was purified by flash chromatography (alumina, ethyl acetate/gradient of methanol from 0 up to 4%) to give compound 21 as an oil (200 mg, 0.34 mmol, 25%). Rf : 0.40 (alumina, eluent mixture A); 1H NMR (DMSO-d6, 200 MHz) delta 0.84 (m, 6H, H3delta), 1.22 (t, 6H, J = 8 Hz, H11'), 1.66 (m, 3H, H3beta, H3gamma), 2.61 (s, 3H, SCH3), 3.10 (q, 4H, J = 8 Hz, H10'), 3.18 (t, 2H, J = 8 Hz, H8'), 3.64 (m, 2H, H7'), 4.08 (m, 2H, H6beta), 4.70 (m, 1H, H3), 4.92 (m, 1H, H6), 5.90 (d, 1H, J = 16 Hz, H1), 6.05 (d, 1H, J = 16 Hz, H2), 7.20 (m, 5H), 7.57 (d, 2H, J = 8 Hz, H2'), 8.15 (d, 2H, J = 8 Hz, H3'), 8.60 (brs, 1H, H4), 8.01 (brs, 1H, H6'), 8.80 (d, 1H, J = 8.5 Hz, H7); 13C NMR (DMSO-d6, 50.3 MHz) delta 9.5 (2C11'), 20.3, 22.6, 24.9 (2Cdelta, Cgamma), 35.9 (Cbeta), 36.0 (C7'), 37.5 (Cbeta), 39.3 (2C10'), 46.4 (SO2CH3), 51.9 (C8'), 54.9 (C6), 62.1 (C3), 116.0 (C1), 126.1-130.0 (2C2', 2C3', 5CPhe), 136.2 (C1' or C4', CPhe), 136.5 (C1' or C4'), 140.5 (C2), 165.9, 166.0, 171.5 (C5, C8, C5'); IR (KBr) 3269.80, 2956.78, 1644.72, 1540.40, 1300.11, 1133.47 cm-1; MS: m/z = 585.23 [M + H]+, Anal. (C31H44N4O5S, 10H2O) C, N.
  • 76
  • <i>N</i>-(2-diethylamino-ethyl)-<i>N</i>'-{1-[1-(1-formyl-3-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-3-methyl-butyl}-terephthalamide [ No CAS ]
  • [ 40137-11-9 ]
  • [ 1346804-68-9 ]
YieldReaction ConditionsOperation in experiment
42% General procedure: A solution of 19 (482 mg, 2.09 mmol, 1.5 eq) in dry tetrahydrofuran (10 mL) was added at -70 C under nitrogen to a solution of sodium hydride 60% in mineral oil (83.6 mg, 2.09 mmol, 1.5 eq) in dry tetrahydrofuran (10 mL). After 30 min at -70 C, a solution of 20 (710 mg, 1.39 mmol, 1 eq) in dry tetrahydrofuran (10 mL) was added to the mixture. After return back to room temperature, the reaction was quenched with methanol (4 mL). The reaction mixture was evaporated under vacuum, then diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic layer was washed with aqueous saturated sodium bicarbonate solution (100 mL), dried with magnesium sulphate, filtered and evaporated under vacuum. The crude product was purified by flash chromatography (alumina, ethyl acetate/gradient of methanol from 0 up to 4%) to give compound 21 as an oil (200 mg, 0.34 mmol, 25%).
  • 77
  • <i>N</i>-(2-diethylamino-ethyl)-<i>N</i>'-{1-[1-(1-formyl-3-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-terephthalamide [ No CAS ]
  • [ 40137-11-9 ]
  • [ 1346804-70-3 ]
YieldReaction ConditionsOperation in experiment
27% General procedure: A solution of 19 (482 mg, 2.09 mmol, 1.5 eq) in dry tetrahydrofuran (10 mL) was added at -70 C under nitrogen to a solution of sodium hydride 60% in mineral oil (83.6 mg, 2.09 mmol, 1.5 eq) in dry tetrahydrofuran (10 mL). After 30 min at -70 C, a solution of 20 (710 mg, 1.39 mmol, 1 eq) in dry tetrahydrofuran (10 mL) was added to the mixture. After return back to room temperature, the reaction was quenched with methanol (4 mL). The reaction mixture was evaporated under vacuum, then diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic layer was washed with aqueous saturated sodium bicarbonate solution (100 mL), dried with magnesium sulphate, filtered and evaporated under vacuum. The crude product was purified by flash chromatography (alumina, ethyl acetate/gradient of methanol from 0 up to 4%) to give compound 21 as an oil (200 mg, 0.34 mmol, 25%).
  • 78
  • [ 28460-01-7 ]
  • [ 937-14-4 ]
  • [ 40137-11-9 ]
YieldReaction ConditionsOperation in experiment
39% In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; Step A: To 3-chlorobenzoperoxoic acid (77%, 11.21 g, 50 mmol) in DCM (150 mL) was added diethyl methylthiomethylphosphonate (4.4 mL, 25 mmol) and the mixture was allowed to stir at room temperature overnight. Additional 3-chlorobenzoperoxoic acid (5.6 g) was then added and stirring was continued for 4 hrs at room temperature. The solution was washed with saturated aq potassium carbonate and concentrated. The residue was dissolved in DCM and washed again with a saturated potassium carbonate solution. The organic layer was concentrated to afford diethyl methylsulfonylmethylphosphonate (4.51 g, 39%). 1H NMR (300 MHz, DMSO-d6) delta1.25 (t, 6H) 3.13 (s, 3H) 4.09 (m, 4H) 4.20 (d, 2H); LC-MS (ESI) m/z 231 (M+H)+.
  • 79
  • [ 40137-11-9 ]
  • [ 1361310-13-5 ]
  • [ 1361310-46-4 ]
YieldReaction ConditionsOperation in experiment
Step B: To <strong>[40137-11-9]diethyl methylsulfonylmethylphosphonate</strong> (746 mg, 3.24 mmol) in THF (20 mL) at 0 C. was added potassium t-butoxide (1.0 M in THF, 3.25 mL, 3.25 mmol) and the mixture was stirred for 5 min. Then (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone from Example 1 (1 mmol) is added and the mixture is stirred at rt for 4 to 8 h or until the reaction is substantially complete. After acidic aqueous workup, the crude product is purified by silica gel chromatography. The isolated product in an EtOAc/EtOH mixture is then hydrogenated in the presence of 10% Pd-C. Additional catalyst is added and the reaction is allowed to continue as needed until the reaction is substantially complete. The mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography to afford (R,S)-2-(1-(5-fluoropyridin-2-yl)-2-(methylsulfonyl)ethyl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine.
  • 80
  • [ 40137-11-9 ]
  • (S)-tert-butyl 4-(3-(methoxy(methyl)amino)-3-oxo-2-(tritylamino)propyl)benzylcarbamate [ No CAS ]
  • (S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-(tritylamino)but-3-en-1-yl)benzylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; LiAlH4; NaH; In tetrahydrofuran; diethyl ether; ethyl acetate; mineral oil; (S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-(tritylamino)but-3-en-1-yl)benzylcarbamate (17) Weinreb amide 16 (0.65 g, 1.12 mmol) was dissolved in Et2O (15 mL), put under an argon atmosphere and cooled to 0 C. LiAlH4 (2 eq., 2.25 mmol, 0.56 mL of a 4 M solution in Et2O) was added slowly and the mixture was stirred at 0 C. for 1 hour after which TLC analysis indicated complete conversion of the starting compound. 0.1 M aq. HCl (15 mL) was slowly added and the layers were separated. The organic layer was extracted with 0.1 M aq. HCl and brine, dried over MgSO4 and concentrated under reduced pressure. Diethyl ((methylsulfonyl)methyl)phosphonate (1.5 eq., 1.68 mmol, 0.39 g) was dissolved in THF (20 mL) and cooled to 0 C. under an argon atmosphere. NaH (1.5 eq., 1.68 mmol, 67.2 mg, 60% w/w in mineral oil) was slowly added and the mixture was stirred at 0 C. for 30 minutes. Next, the freshly obtained aldehyde (in THF (2 mL)) was slowly added and the mixture was stirred for 2 hours while slowly warming it to room temperature. After this time TLC analysis indicated complete conversion of the aldehyde. EtOAc (20 mL) was added and the mixture was extracted with mM aq. HCl (2*) and brine, dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained after column chromatography (20%?50% EtOAc/PE) as a colourless foam (yield: 0.57 g, 0.95 mmol, 85%). 1H NMR (400 MHz, CDCl3): delta=7.46 (d, J=7.6 Hz, 6H), 7.28 (t, J=7.20, 6.80 Hz, 6H), 7.20 (t, J=7.20, 7.20 Hz, 3H), 7.13 (d, J=7.60 Hz, 2H), 6.87 (d, J=8.00 Hz, 2H), 6.57 (dd, J=14.80, 7.00 Hz, 1H), 5.96 (d, J=14.80 Hz, 1H), 4.80 (s, 1H), 4.24 (d, J=5.60 Hz, 2H), 3.49 (q, J=6.00 Hz, 1H), 2.61 (s, 3H), 2.54 (dd, J=13.20, 5.20 Hz, 1H), 2.33 (dd, J=13.20, 8.20 Hz, 1H), 1.44 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): delta=155.59, 150.21, 145.74, 137.42, 135.28, 129.53, 128.35, 128.02, 127.70, 127.14, 126.44, 78.91, 71.05, 55.33, 43.79, 42.43, 41.86, 28.09 ppm. [alpha]D?=-21.3 (c=1, CHCl3). HRMS: calcd. for C36H40N2O4S 619.26010 [M+Na]+. Found 619.26001.
  • 81
  • [ 40137-11-9 ]
  • [ 1389327-26-7 ]
  • [ 1389326-67-3 ]
YieldReaction ConditionsOperation in experiment
Step C: (EVmethyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)vinyl)-lH-indol-l-yl)butanoateTo a solution of <strong>[40137-11-9]diethyl methylsulfonylmethylphosphonate</strong> (1.05 g, 4.56 mmol) in CH3CN (30 mL) at RT was added LiCl (0.16 g, 3.80 mmol) and DBU (2.40 g, 9.56 mmol). After 5 min, a solution of methyl 2-(4-chlorophenyl)-2-(4-formyl-lH-indol-l-yl)butanoate (1.35 g, 3.80 mmol) in CH3CN (10 mL) was added dropwise. The resulting mixture was stirred for 4 hours at RT. Then it was diluted with DCM (50 mL) and the organic layer was washed with water (30 mL), dried over Na2S04, filtered. After removal of the solvent, the residue was purified via column chromatography (0-30 % EtOAc/hexanes) to provide the title compound. LC/MS m/z = 432.0[M+H]+.
  • 82
  • (4S,4aS,10bS)-10b-((4-chlorophenyl)sulfonyl)-7,10-difluoro-1,2,4,4a,5,10b-hexahydropyrano[3,4-c]chromene-4-carbaldehyde [ No CAS ]
  • [ 40137-11-9 ]
  • (4S,4aS,10bS)-10b-((4-chlorophenyl)sulfonyl)-7,10-difluoro-4-((E)-2-(methylsulfonyl)vinyl)-1,2,4,4a,5,10b-hexahydropyrano[3,4-c]chromene [ No CAS ]
  • (4S,4aS,10bS)-10b-((4-chlorophenyl)sulfonyl)-7,10-difluoro-4-((Z)-2-(methylsulfonyl)vinyl)-1,2,4,4a,5,10b-hexahydropyrano[3,4-c]chromene [ No CAS ]
  • 83
  • [ 40137-11-9 ]
  • [ 131118-61-1 ]
  • [ 1417177-64-0 ]
YieldReaction ConditionsOperation in experiment
175 mg General procedure: In a separate flask, <strong>[40137-11-9]diethyl((methylsulfonyl)methyl)phosphonate</strong> 6 (553 mg, 2.4 mmol) was dissolved in anhydrous THF (20 mL) under argon atmosphere. The mixture was brought to -78 C and n-BuLi (1.6 M in hexanes, 1.38 mL, 2.2 mmol) was added slowly and stirred for 15 min. The solution of the above aldehyde 13 (2 mmol) in anhydrous THF (15 mL) was added dropwise. The flask was kept at -78 C for 1 h and at room temperature overnight (18 h). Water (10 mL) was added and the product extracted in ethyl acetate (3 × 50 mL). The combined organic layers were washed with brine, dried over anhyd Na2SO4, filtered and filtrate was evaporated. The residue was purified by flash column chromatography (20-50% EtOAc in hexanes) to afford 14 as white solid (175 mg, 20%). 1H NMR (300 MHz, CDCl3) delta ppm 0.03 (s, 3H, SiMe), 0.04 (s, 3H, SiMe), 0.84 (s, 9H, t-Bu), 1.89 (d, J = 1.17 Hz, 3H, 5-Me), 2.16-2.24 (m, 2H, 2?-H), 2.91 (s, 3H, SO2Me), 4.25 (dt, J = 6.37, 4.87 Hz, 1H, 3?-H), 4.33-4.43 (m, 1H, 4?-H), 6.22 (t, J = 6.74 Hz, 1H, 1?-H) 6.62 (dd, J = 15.08, 1.90 Hz, 1H, 6?-H), 6.93 (dd, J = 14.94, 4.10 Hz, 1H, 5?-H), 6.96 (d, J = 1.17 Hz, 1H, 6-H), 8.39 (s, 1H, NH). 13C NMR (75 MHz, CDCl3) delta ppm -4.78 (SiMe-C), -4.66 (SiMe-C), 12.64 (5Me-C), 17.90 (tBu-tC), 25.63 (tBuMe-C), 39.46 (2?-C), 42.68 (SO2Me-C), 74.66 (3?-C), 84.05 (4?-C), 85.56 (1?-C), 111.93 (5-C), 130.75 (6?-C), 135.28 (6-C), 142.90 (5?-C), 150.00 (2-C), 163.14 (4-C). ESI-HRMS for [C18H30N2O6SSi+H]+ Calcd, 431.1672. Found, 431.1519.
  • 84
  • [ 40137-11-9 ]
  • [ 1417177-81-1 ]
  • [ 1417177-82-2 ]
YieldReaction ConditionsOperation in experiment
29% General procedure: In a separate flask, <strong>[40137-11-9]diethyl((methylsulfonyl)methyl)phosphonate</strong> 6 (553 mg, 2.4 mmol) was dissolved in anhydrous THF (20 mL) under argon atmosphere. The mixture was brought to -78 C and n-BuLi (1.6 M in hexanes, 1.38 mL, 2.2 mmol) was added slowly and stirred for 15 min. The solution of the above aldehyde 13 (2 mmol) in anhydrous THF (15 mL) was added dropwise. The flask was kept at -78 C for 1 h and at room temperature overnight (18 h). Water (10 mL) was added and the product extracted in ethyl acetate (3 × 50 mL). The combined organic layers were washed with brine, dried over anhyd Na2SO4, filtered and filtrate was evaporated. The residue was purified by flash column chromatography (20-50% EtOAc in hexanes) to afford 14 as white solid (175 mg, 20%).
  • 85
  • [ 181308-57-6 ]
  • [ 40137-11-9 ]
  • [ 1315499-03-6 ]
YieldReaction ConditionsOperation in experiment
100% Trans 4-(2-Methanesulfonyl-ethyl)-cyclohexylamineTrans [4-(2-Methanesulfonyl-vinyl)-cyclohexyl]-carbamic acid tert-butyl esterA solution of diethyl methanesulfonylmethyl phosphonate (900 mg, 3.90 mmol) in THF (20 mL) was treated with sodium hydride (160 mg of a 60% dispersion in mineral oil, 4.00 mmol). The mixture was stirred for 1 hour to give a thick slurry. Trans (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (975 mg, 4.30 mmol) was added and the slurry thinned. The mixture was stirred for 2 hours. A few drops of methanol were added and after 5 minutes the solvent removed under vacuum. The residue was partitioned between water (25 mL) and DCM (25 mL). The aqueous phase was washed with DCM (2 x 10 mL). The combined organic phase was dried over magnesium sulfate and concentrated under vacuum to afford 1.30 g (100%) of crude trans [4- (2-methanesulfonyl-vinyl)-cyclohexyl]-carbamic acid tert-butyl ester as a white solid (? NMR showed -4: 1 mixture of double bond geometries).Major isomer ? NMR (400 MHz, CDC13): delta 6.88 (dd, 1 H), 6.32 (dd, 1 H), 4.39 (br s, 1 H), 3.40 (br s, 1 H), 2.93 (s, 3 H), 2.21-1.98 (m, 3 H), 1.91-1.78 (m, 2 H), 1.44 (s, 9 H), 1.35-1.09 (m, 4 H).
  • 86
  • [ 23100-12-1 ]
  • [ 40137-11-9 ]
  • [ 1542235-14-2 ]
  • 87
  • 1-[(tert-butyldimethylsilyl)oxy]-1-(5-tributylstannyloxazol-2-yl)-7-phenylheptane [ No CAS ]
  • [ 40137-11-9 ]
  • [ 1542235-19-7 ]
  • 88
  • [ 40137-11-9 ]
  • [ 1352076-39-1 ]
  • [ 1559022-71-7 ]
  • 89
  • [ 181308-57-6 ]
  • [ 40137-11-9 ]
  • [ 1418002-87-5 ]
  • [ 1418002-88-6 ]
YieldReaction ConditionsOperation in experiment
To a solution of 1.0 M potassium tert-butoxide in tetrahydrofuran (THF) (1.0 mL, 1.0 mmol) was added <strong>[40137-11-9]diethyl [(methylsulfonyl)methyl]phosphonate</strong> (0.21 g, 0.92 mmol) dropwise at 0 C. and the resulting mixture was stirred at 0 C. for 1 h. A solution of tert-butyl (trans-4-formylcyclohexyl)carbamate (0.15 g, 0.66 mmol) in tetrahydrofuran (4.6 mL) was added dropwise, then cooling bath was removed and the mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, washed with water, concentrated and purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (0.14 g, 70%) as a mixture of E- and Z-isomers. LCMS calculated for C14H25NO4SNa (M+Na)+: m/z=326.2. Found: 326.1
  • 90
  • [ 40137-11-9 ]
  • [ 1607803-68-8 ]
  • C21H23NO8S [ No CAS ]
  • 91
  • [ 40137-11-9 ]
  • [ 89711-08-0 ]
  • [ 139200-37-6 ]
YieldReaction ConditionsOperation in experiment
56% Sodium hydride (60 % dispersion in mineral oil) (233.2 mg, 5.83 mmol) in tetrahydrofuran (0.17 M, 34.3 mL) was cooled to 0 C with stirring, followed by the dropwise addition of diethyl(methylsulfonylmethyl)phosphonate (Oakwood) (1342.2 mg, 5.83 mmol) in 5 mL THF. The reaction was stirred at 0 Cfor 20 min, then 12 (928 mg, 5.83 mmol) in 5 mL THF was added. The reaction was allowed to warm to 23 C and was stirred for 1 h. TLC showed conversion to the product. THF was removed under reduced pressure, and the residue was then diluted with ethyl acetate (30 mL) and water (30 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2x30 mL). The organic layer was then dried over MgSO4, filtered, and evaporated.The residue was purified by flash column chromatography with an ethyl acetate/hexanes gradient 25 % EtOAc ? 50% EtOAc to yield 15 (530.4 mg, 56 % yield). 1HNMR (400 MHz, CDCl3) delta 6.38 (dd, J = 11.7, 5.8 Hz, 1H), 6.28 (dt, J= 11.4, 1.7 Hz, 1H), 5.01 (s, 1H), 4.23 (td, J = 6.3, 1.7 Hz, 2H), 3.00 (s,3H), 1.41 (s, 9H).
  • 92
  • [ 40137-11-9 ]
  • [ 98105-42-1 ]
  • [ 1620107-78-9 ]
  • 93
  • [ 40137-11-9 ]
  • [ 166655-48-7 ]
  • C21H31ClN2O6S [ No CAS ]
  • 94
  • [ 40137-11-9 ]
  • [ 118546-67-1 ]
  • C17H25NO4S2 [ No CAS ]
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