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Chemical Structure| 146374-27-8
Chemical Structure| 146374-27-8
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Product Details of [ 146374-27-8 ]

CAS No. :146374-27-8 MDL No. :MFCD01863616
Formula : C4H11NOS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :121.20 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 146374-27-8 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.36
TPSA : 62.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.09
Log Po/w (XLOGP3) : 0.03
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : -1.04
Consensus Log Po/w : 0.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.54
Solubility : 34.6 mg/ml ; 0.286 mol/l
Class : Very soluble
Log S (Ali) : -0.89
Solubility : 15.6 mg/ml ; 0.129 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.7
Solubility : 24.1 mg/ml ; 0.199 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.64

Safety of [ 146374-27-8 ]

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 [ 146374-27-8 ]

* 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.

  • Upstream synthesis route of [ 146374-27-8 ]
  • Downstream synthetic route of [ 146374-27-8 ]

[ 146374-27-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 146374-27-8 ]
  • [ 34813-49-5 ]
Reference: [1] Synthesis, 2008, # 2, p. 311 - 319
[2] Chemistry - A European Journal, 2004, vol. 10, # 4, p. 906 - 916
[3] Journal of Organic Chemistry, 1981, vol. 46, # 5, p. 1012 - 1014
[4] Chemistry - A European Journal, 2013, vol. 19, # 3, p. 1123 - 1128
[5] Synlett, 2018, vol. 29, # 9, p. 1232 - 1238
  • 2
  • [ 31562-43-3 ]
  • [ 146374-27-8 ]
YieldReaction ConditionsOperation in experiment
9.2 g With ammonia In dichloromethane; water at 20℃; for 1 h; A solution of 2-methylpropanethiol (14.1cm3, 125mmol) in DCM (50mL) was cooled to −40°C and at 30min intervals, a slurry (50mL) of a suspension of m-chloroperbenzoic acid (63.2g, 256mmol, 2.05equiv) in DCM (500mL) cooled to −78°C was added in portions with vigorous stirring (exothermic reaction) over 10h. The resulting white suspension was stirred at −30°C overnight, then cooled to −78°C and filtered. The filtrate was concentrated under reduced pressure then dried under high vacuum to provide crude tert-butanesulfinic acid (13.5g, 88percent). Thionyl chloride (40.3mL, 552.5mmol, 5equiv). was added to this sulfinic acid at −40°C under nitrogen and the yellow solution was allowed to warm to rt and was stirred for 2h. Concentration under high vacuum gave tert-butylsulfinyl chloride (12.9g, 83percent) as a brown oil. This sulfinyl chloride in DCM (582mL) was added to aqueous ammonia (38percent in water 582mL, 220mmol, 2.4equiv) and the mixture stirred at rt for 1h. The aqueous layer was then saturated with NaCl and extracted with DCM (4×600cm3). The organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield the title compound (9.2g, 83percent) as a white solid crystallised from hexane. Rf=0.23 (EtOAc); mp 103–104°C [lit.14 for the (S)-enantiomer 106°C (TCI)]; νmax/cm−1 3231, 2979, 2959, 2928, 2869, 1677, 1570, 1475, 1461, 1364, 1309, 1193, 1132, 1030 and 893; δH (300MHz, CDCl3) 1.19 [9H, s, C(CH3)3] and 3.96 (2H, br s, NH2); δC (75MHz, CDCl3) 22.1 and 55.2; m/z (CI+) 139 (M++18, 100percent) and 122 (M++1, 100).
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 15, p. 5472 - 5478
[2] Tetrahedron Letters, 2009, vol. 50, # 26, p. 3482 - 3484
[3] Journal of the American Chemical Society, 2005, vol. 127, # 7, p. 2104 - 2113
[4] Journal of Organic Chemistry, 2009, vol. 74, # 7, p. 2646 - 2650
[5] Journal of Organic Chemistry, 2009, vol. 74, # 7, p. 2891 - 2892
[6] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 4, p. 1641 - 1658
[7] Tetrahedron, 2016, vol. 72, # 4, p. 451 - 463
  • 3
  • [ 75-28-5 ]
  • [ 146374-27-8 ]
Reference: [1] Patent: CN105753754, 2016, A, . Location in patent: Paragraph 0006
  • 4
  • [ 842121-02-2 ]
  • [ 98-85-1 ]
  • [ 3886-69-9 ]
  • [ 146374-27-8 ]
  • [ 98-86-2 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 38, p. 5386 - 5388
  • 5
  • [ 842121-02-2 ]
  • [ 146374-27-8 ]
  • [ 98-86-2 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 38, p. 5386 - 5388
  • 6
  • [ 842121-02-2 ]
  • [ 98-85-1 ]
  • [ 2627-86-3 ]
  • [ 3886-69-9 ]
  • [ 146374-27-8 ]
  • [ 98-86-2 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 38, p. 5386 - 5388
  • 7
  • [ 6704-31-0 ]
  • [ 146374-27-8 ]
  • [ 1158098-73-7 ]
YieldReaction ConditionsOperation in experiment
76% With titanium(IV) isopropylate In ethanol at 80℃; for 8 h; 3-oxetanone (0.5g, 7mmol) with tert-butylsulfinamide(0.9g, 7mmol) Soluble in ethanol (30mL), Add titanium tetraisopropoxide (2g, 7mmol), Stir at 80 ° C for 8 hours. Add 1N sodium hydroxide solution (10 mL),Stir at room temperature for 2 hours. The reaction solution was concentrated to dryness.Purified by silica gel column chromatography,A white solid (0.6 g, 76percent) was obtained.
48% With titanium(IV) tetraethanolate In tetrahydrofuran at 60℃; for 18 h; Step 1:
Preparation of 2-methyl-N-oxetan-3-ylidenepropane-2-sulfinamide
To a solution of 2-methyl-2-propanesulfinamide (1.47 g) and 3-oxetanone (0.85 mL) in THF (24 mL) was added Ti(OEt)4 (5.34 mL) dropwise over the course of 15 minutes at room temperature.
After being stirred at 60° C. for 18 h, the reaction mixture was quenched by the rapid addition into ice cooled saturated sodium bicarbonate aqueous solution.
The suspension was filtered through glass fiber filter paper and the cake was washed with ethyl acetate.
The filtrate was washed with saturated sodium bicarbonate solution then brine.
The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure.
Purification by column chromatography (10-100percent ethyl acetate in hexanes) gave the product (1.02 g, 48percent).
1HNMR (CDCl3) 400 MHz δ: 5.80 (ddd, J=15.6, 4.1, 2.3 Hz, 1H), 5.66 (ddd, J=15.6, 4.1, 2.3 Hz, 1H), 5.52-5.41 (m, 2H), 1.27 (s, 9H).
48.1% With titanium(IV) isopropylate In dichloromethane at 20℃; Inert atmosphere; Reflux To a 100 mL round-bottom flask were added oxetan-3-one (1.62 mL, 27.9 mmol), 2-tert-butyl2-sulfinamide (4.0 g, 33 mmol) and anhydrous DCM (30 mL), then to the mixture was added titanium iso-propylate (16.6 mL) over 40 min via constant pressure funnel at rt under nitrogen protection.
After the addition, the mixture was refluxed overnight.
After the reaction was completed, the reaction mixture was cooled to rt, and saturated aqueous sodium bicarbonate (100 mL) was added.
The resulting mixture was stirred for 20 min, then diatomite was added to filter the mixture by suction.
After the mixture was filtered, the filter cake was washed with dichoromethane (20 mL).
The combined filtrates were extracted with DCM (30 mL*2), and the combined organic layers were dried over anhydrous sodium sulfate, and filtered.
The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (n-hexane:EtOAc=1:1, V/V) to give colourless oil (2.35 g, 48.1percent).
MS (ESI, pos. ion) m/z: 176.1 (M+1);
46% With titanium(IV) tetraethanolate In tetrahydrofuran at 50℃; for 5 h; To Oxetan-3-one (5 g, 69 mmol) in THF (50 mL) 2-methylpropane-2-sulfinamide (8.34 g, 69 mmol) and Ti(OEt)4 (20 mL) were added sequentially. The reaction was heated to 50°C for 5 hours. The reaction was cooled to room temperature and quenched with water (200 mL). The precipitate was filtered and the filtrate was extracted with CH2C12 (2 x 50 mL). The combined organic layer was separated and washed with water (50 mL) and brine (50 mL). The organic layer was dried and concentrated. The crude product was purified by column chromatography (CH2C12) to afford compound 62 (5.5 g, 46 percent yield).
46% With titanium(IV) tetraethanolate In tetrahydrofuran at 50℃; for 5 h; To Oxetan-3-one (5 g, 69 mmol) in THF (50 mL) 2-methylpropane-2-sulfinamide (8.34 g, 69 mmol) and Ti(OEt)4 (20 mL) were added sequentially. The reaction was heated to 50°C for 5 hours. The reaction was cooled to room temperature and quenched with water (200 mL). The precipitate was filtered and the filtrate was extracted with CH2CI2 (2 x 50 mL). The combined organic layer was separated and washed with water (50 mL) and brine (50 mL). The organic layer was dried and concentrated. The crude product was purified by column chromatography (CH2CI2) resulting in compound OA-1 (5.5 g, 46 percent yield).
46% With titanium(IV) tetraethanolate In tetrahydrofuran at 50℃; for 5 h; Inert atmosphere; Sealed tube To a solution of compound 5-1 (4.97 g, 69 mmol) in THF (50 mL) was added compound 5-1-2 (8.35 g, 69 mmol) and Ti(OEt)4 (20 mL) dropwise. At the end of the addition, the mixture was stirred at 50 °C for 5.0 hrs. After the reaction was completed, the mixture was cooled to rt and quenched with water (200 mL). The resulting mixture was filtered and the filtrate was extracted with DCM (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM) to give the title compound as a solid (5.5 g, 46percent). The compound was characterized by the following spectroscopic data: NMR (400 MHz, CDC13) δ (ppm): 5.39 (s, 4H), 1.31 (s, 9H).
46% With titanium(IV) tetraethanolate In tetrahydrofuran at 50℃; for 5 h; To a u oun - . g, mmo n . m w as a e con mmol) and Ti(OEt)4 (20.0 mL). At the end of the addition, the mixture was stirred at 50 °C for 5.0 hrs. After the reaction was completed, the mixture was cooled to rt and quenched with 200 mL of water. The resulting mixture was filtered and the filtrate was extracted with DCM (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated //; vacuo. The residue was purified by silica gel column chromatography (DCM) to give the title compound as a solid (5.55 g, 46percent). The compound was characterized by the following spectroscopic data: NMR (400 MHz. CDCL) δ (ppm): 5.39 (s, 4H), 1 .31 (s, 9H).
45.4% With titanium(IV) tetraethanolate In tetrahydrofuran at 22 - 50℃; for 5 h; Preparation of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulflnamide; 2-Methylpropane-2-sulfinamide (3.36 g, 27.77 mmol, leq) and Ti(OEt)4 (12 ml, 55.54 mmol, 2eq) were added to a solution of oxetan-3-one (2 g, 27.77 mmol, leq) in THF at 22 °C. The reaction mixture was stirred at 50 °C for 5 h. It was cooled to room temperature and poured into saturated brine solution, and then the suspension was filtered through a pad of Cellite. The filtrate was extracted with ethyl acetate, and the organic layer washed with saturated brine solution, dried over Na2S04 and concentrated. The crude product was purified by silica gel (60-120 mesh) columatography using 30percent EtOAc/Petroleum ether. Yield: 0.55g (45.4percent). 3/4 NMR (400 MHz, DMSO-d6) 5.66-5.42 (m, 4H), 1.19 (s, 9H).
44% With titanium(IV) isopropylate In tetrahydrofuran at 50℃; for 16 h; 2-Methyl-2-propanesulfinamide (25.9 g, 214 mmol) followed by Ti(OiPr) (1 10 g, 389 mmol) were added to a solution of oxetan-3-one (14.0 g, 194 mmol) in anhydrous THF (250 mL) and the reaction mixture was heated at 50 °C for 16 hrs. The reaction mixture was cooled in an ice bath, anhydrous MeOH (140 mL) was added followed by sat. aq. NaHCO3 (20 mL) and the resulting suspension stirred for 1 hr. The solids were filtered off washing through with EtOAc. The filtrate was dried (Na2SO4) and concentrated in vacuo.The crude product was purified by column chromatography on silica gel column eluting with pet. Ether: EtOAc (100:0 to 80:20) to give the title product as a pale yellow oil, 15.0 g, 44percent. 1H NMR (400 MHz, CDCI3): δ 1 .25 (s, 9H), 5.38-5.50 (m, 2H), 5.61 - 5.67 (m, 1 H), 5.74-5.81 (m, 1 H). LCMS m/z = 176 [M+H]+
43% With titanium(IV) tetraethanolate In tetrahydrofuran at 50℃; for 16 h; Titanium (IV) ethoxide (0.25 mL, 1.2 mmol, 2.0 equiv) was added to a solution of oxetane-3-one (43 mg, 0.59 mmol, 1 equiv) and 2-methylpropane-2-sulfinamide (72 mg, 0.59 mmol, 1 equiv) in tetrahydrofuran (1.1 mL) at 22 °C. The reaction mixture was healed to 50 °C for 16 hours, then was cooled to 22 °C and poured over stirring saturated aqueous sodium chloride solution (3 mL). The suspension was filtered through celite with the aid of ethyl acetate, and the filtrate was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, and the dried solution was filtered. The filtrate was concentrated to give 2-methyl-N-oxetan-3-ylidenepropane-2- sulfinamide (43 mg, 43percent) as a light-yellow oil. Calc'd (M+l)+: 176.1 , Found: 176.1.
29% With titanium(IV) isopropylate In tetrahydrofuran at 20 - 60℃; Inert atmosphere To a solution of 2-methylpropane-2-sulfinamide (2.424 g, 20 mmol) and oxetan-3-one (1.41 mL, 24 mmol) in THF (40 mL) was added dropwise over 15 mm Titanium (IV) ethoxide (8.38 mL, 40 mmol) under a nitrogen atmosphere at RT and the mixture was stirred at 60 °C overnight. The reaction mixture was allowed to cool to RT. The mixture was quenched with chilled aqueous saturated NaHCO3 and diluted with EtOAc. Thesuspension was filtered through diatomaceous earth and the organic layer was washed with aqueous saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified by chromatography over silica gel (gradient of EA in heptane from 10 to 100percent). The fractions with product were collected and concentrated under reduced pressure to yield 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1 g,29percent). ‘HNMR (300 IVIHz, Chloroform-d) 1.28 (s, 9H), 5.37—5.58 (m, 2H), 5.61 —5.87 (m, 2H). C7H13N02S MS m/z 176.1 (M+H).
22.9% With titanium(IV) isopropylate In dichloromethane at 20 - 50℃; for 23 h; Oxetan-3-one (0.81 mL, 13.88 mmol) and 2-methylpropane-2-sulfinamide (1.85 g, 15.26 mmol) were combined in DCM (34 mL). While the mixture was stirred vigorously, titanium(IV) isopropoxide (7.2 mL, 27.8 mmol) was added dropwise. The resulting mixture was then heated at 50 °C for 5h, cooled and then stirred at roomtemperature for 1 8h. The reaction mixture was poured into 20 mL of NaHCO3 solution and stirred vigorously. After 20 mm, the resulting heterogeneous mixture was filtered through a pad of CELITE®, the filtrate was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified by 12 g silica gel cartridge eluting with a 14 mm gradient from 0-50percenthexane/ethyl acetate to obtain 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (557 mg, 3.18 mmol, 22.90percent yield) as a yellow oil. ‘H NMR (400MHz, CDC13) ö 5.84-5.76 (m, 1H), 5.71-5.61 (m, 1H), 5.55-5.39 (m, 2H), 1.29-1.25 (m, 9H). LC/MS: Rt =0.62 mi [M+1] = 176 (Method M).
19% With titanium(IV) tetraethanolate In tetrahydrofuran at 40℃; for 72 h; Preparation 392- Methyl-A/-oxetan-3-ylidenepropane-2-sulfinamide3- Oxetanone (3 g, 41 .63 mmol), terf-butyl sulfinamide (5.55 g, 45.8 mmol) and titanium (IV) ethoxide (13.5 ml_, 62.4 mmol) were stirred in THF (200 ml_) at 40°C for 72 hours. The mixture was cooled to room temperature and poured into a rapidly stirred aqueous solution of saturated sodium chloride (200 ml_). The resulting suspension was filtered through Celite® and the filter cake washed with ethyl acetate. The organic layer was separated and washed with brine, then dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound as an oil (1 .37 g, 19percent yield). 1HNMR (CDCI3): ? 1 .3 (s, 9H), 5.4-5.5 (m, 2H), 5.65 (m, 1 H), 5.8 (m, 1 H).
1.18 g With titanium(IV) tetraethanolate In tetrahydrofuran at 50℃; for 4 h; To a solution of oxetan-3-one (759mg) in THF (30ml) were added 2-methyl-2-propane- sulfinamide (1.25g)and titanium (IV) ethoxide (4.4ml). The reaction mixture was stirred at 50°C for 4h. The mixture was diluted with sat. aq. NaCI (200ml)and the suspension was filtrated through a pad of celite and washed with EA. Both layers of the filtrate were separated and the aq. layer was extracted with EA. The combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Flash Master, solvent A: heptane, solvent B: EA, gradient in percentB: 20, flow rate: 20ml/min) to afford 1.18g of a yellow oil. LC-MS (A): tR = 0.55min; [M+H]+: 176.26.

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[2] Patent: CN108341814, 2018, A, . Location in patent: Paragraph 0217-0218; 0220-0222
[3] Patent: US2012/108574, 2012, A1, . Location in patent: Page/Page column 115
[4] Patent: EP3342765, 2018, A1, . Location in patent: Paragraph 0231
[5] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 64
[6] Patent: WO2013/98313, 2013, A1, . Location in patent: Page/Page column 47; 48
[7] Patent: WO2014/82380, 2014, A1, . Location in patent: Paragraph 00371; 00372
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[10] Patent: WO2012/78545, 2012, A1, . Location in patent: Page/Page column 23-24
[11] Patent: WO2018/11681, 2018, A1, . Location in patent: Page/Page column 102
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[13] Patent: WO2017/123542, 2017, A1, . Location in patent: Page/Page column 386
[14] Patent: WO2016/64957, 2016, A1, . Location in patent: Page/Page column 123; 124
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  • [ 922500-97-8 ]
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  • [ 1158098-73-7 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 5, p. 1116 - 1119
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