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Product Details of [ 3144-09-0 ]

CAS No. :3144-09-0 MDL No. :MFCD00007940
Formula : CH5NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :HNQIVZYLYMDVSB-UHFFFAOYSA-N
M.W : 95.12 Pubchem ID :72879
Synonyms :

Calculated chemistry of [ 3144-09-0 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 18.59
TPSA : 68.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.4
Log Po/w (XLOGP3) : -1.07
Log Po/w (WLOGP) : -0.01
Log Po/w (MLOGP) : -2.12
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : -0.76

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.24
Solubility : 167.0 mg/ml ; 1.76 mol/l
Class : Highly soluble
Log S (Ali) : 0.12
Solubility : 125.0 mg/ml ; 1.32 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.25
Solubility : 171.0 mg/ml ; 1.79 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 3144-09-0 ]

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 [ 3144-09-0 ]

* 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 [ 3144-09-0 ]
  • Downstream synthetic route of [ 3144-09-0 ]

[ 3144-09-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 67-56-1 ]
  • [ 3144-09-0 ]
  • [ 1184-85-6 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 21, p. 5790 - 5793
[2] ACS Catalysis, 2018, vol. 8, # 7, p. 6440 - 6445
[3] Journal of Catalysis, 2017, vol. 347, p. 57 - 62
  • 2
  • [ 3144-09-0 ]
  • [ 74-88-4 ]
  • [ 1520-70-3 ]
  • [ 918-05-8 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 10, p. 1700 - 1703
  • 3
  • [ 594-43-4 ]
  • [ 3144-09-0 ]
  • [ 1520-70-3 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 39, p. 7201 - 7204
  • 4
  • [ 110-63-4 ]
  • [ 3144-09-0 ]
  • [ 55-98-1 ]
YieldReaction ConditionsOperation in experiment
91% at 5 - 40℃; for 4 h; In the reaction vessel was added 1,4-butanediol (2) 0.15mol, triethylamine 170ml, the temperature of the solution is reduced to 5 , controlling the stirring speed 160rpm, methanesulfonic acid was slowly added to the amine (3) 0.38mol, dropwise Upon completion, the solution temperature rises to 40 , stirred for 4h, the temperature of the solution is reduced to 20 , the precipitated solid was filtered, washed with sodium nitrite solution, dried over anhydrous magnesium sulfate, recrystallized from cyclohexane to 95percent (mass fraction), as a white solid of 1,4-bis-methyl sulfonate polybutyleneterephthalate 33.58g, yield 91percent.
Reference: [1] Patent: CN105566173, 2016, A, . Location in patent: Paragraph 0014; 0015
  • 5
  • [ 3144-09-0 ]
  • [ 99-90-1 ]
  • [ 5317-89-5 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 43, p. 7295 - 7298
[2] Organic Letters, 2011, vol. 13, # 10, p. 2564 - 2567
[3] Green Chemistry, 2014, vol. 16, # 3, p. 1480 - 1488
  • 6
  • [ 3144-09-0 ]
  • [ 1197186-15-4 ]
  • [ 115256-11-6 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 10, p. 2564 - 2567
  • 7
  • [ 75142-05-1 ]
  • [ 3144-09-0 ]
  • [ 5347-82-0 ]
  • [ 2386-57-4 ]
  • [ 41921-91-9 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 351 - 354
  • 8
  • [ 3144-09-0 ]
  • [ 24424-99-5 ]
  • [ 147751-16-4 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine In dichloromethane at 25℃; for 2 h; e)
Boc-N-(4-Benzylsulfanyl-5-nitro-thiophen-3-ylmethyl)-methanesulfonamide
Triethylamine (22.0 mL, 158 mmol), di-tert-butyl dicarbonate (27.5 g, 126 mmol), and 4-(N,N-dimethylamino)pyridine (1.28 g, 10.5 mmol) were added sequentially to a solution of methanesulfonamide (10.0 g, 105 mmol) in dichloromethane (300 mL) at 25° C.
The mixture was stirred at 25° C. for 2 h, and then was concentrated in vacuo to ~40 mL volume.
Ethyl acetate (350 mL) was added and the mixture was washed with 1.0 M aqueous hydrochloric acid solution (300 mL).
The aqueous layer was extracted with ethyl acetate (250 mL) and the combined organic layers were dried over sodium sulfate, filtered and were concentrated in vacuo to afford Boc-N-methanesulfonamide (17.1 g, 87.6 mmol, 83percent) as a white solid. 1H NMR (400 MHz, CDCl3) δ: 1.53 (9H, s), 3.27 (3H, s).
81% With dmap; triethylamine In dichloromethane at 20℃; for 3 h; A solution of Boc20 (41.2 g, 189.2 mmol) in DCM (200 mL) was added dropwise to a stirred suspension of methane sulfonamide (15.0 g, 157.7 mmol), Et3N (23.6 mL, 173.5 mmol) and DMAP (1.9 g, 15.8 mmol) in DCM (200 mL). The resulting suspension was stirred for 3 h at room temperature and concentrated under vacuum. The resulting residue was diluted with EtOAc (300 mL) and acidified with 1 N HCI (200 mL). The organic layer was washed with water followed by brine, dried over Na2S04 and concentrated under reduced pressure to obtain a crude mixture, which was triturated with 10percent EtOAc in petroleum ether to obtain B1 as a white solid (25.0 g, 81 percent). Rf: 0.6 (50percent EtOAc in petroleum ether). LCMS m/z = 194.3 (M - H). 1H NMR (400 MHz, CDCI3): δ 1.44 (s, 9H), 3.19 (s, 3H), 7.19 (s, 1 H).
49% With triethylamine In dichloromethane at 20℃; To a 500 mL row1d bottom f1ask \vas added a solution of methanesulfonamide (1 0 g,105.13 mmol, l.OO equiv.) in dichloromeHume (300 mL) follo·wed by TEA (22 g, 217.4120 mmol, 1.50 equiv.), Boc20 (27.5 g, 126.00 mmoL 1.20 equiv.), and 4-dimethylaminopyridine(1.28 g, 10.48 mmol, 0.10 equiv.). The reaction mixture v.·as stirred at room temperatmeovernight and then concentrated under vacuurn. 200 mL ofFhO vvas added, the pFf value of the solution was adjusted to 3 using a 1M hydrogen chloride aqueous solution, and thernixture was extracted with ethyl acetate (200 mL x 3). The combined organic extracts werew·ashed vvith brine (300 mL x 2), dried over anhydrous sodium sulfate and concentratedunder vacuum to give oftert-butyl N-methanesulfonylcarbamate 216b (10.06 g, 49percent) as a5 ·white solid.
85% With hydrogenchloride; dmap; triethylamine In hexane; dichloromethane; water; ethyl acetate A.
N-(t-butoxycarbonyl)methanesulfonamide

To a solution of 15.0 g (157.7 mmol) of methanesulfonamide, 17.6 g (173.5 mmol) of triethylamine and 1.9 g (15.8 mmol) of 4-dimethylaminopyridine in 200 mL of dichloromethane was added of 37.9 g (173.5 mmol) of di-t-butyldicarbonate in 200 mL of dichloromethane over ten minutes.
The mixture was stirred at ambient temperature for 2.25 hours and concentrated in vacuo.
The residue was dissolved in 250 mL of ethyl acetate and washed once with 200 mL of 1 N hydrochloric acid, once with 100 mL of water and once with 100 mL of saturated aqueous sodium chloride.
The organic layer was dried (MgSO4), filtered and concentrated in vacuo.
The residue was suspended in 100 mL of hexane, filtered and dried in vacuo to afford 26.1 g (85percent) of the title compound.
Analysis calculated for C7H13NO4S: percentC, 36.91; percentH, 6.71; percentN, 7.17.
Found: percentC, 36.97; percentH, 6.79; percentN, 7.04.
Mass Spectrum: M+1=196.
1 g With dmap; triethylamine In dichloromethane at 20℃; for 2 h; Triethylamine (2.2 mL, 16 mmol), di-tert-butyldicarbonate (2.65 g, 12.1 mmol) and 4-dimethylaminopyridine (0.096 g, 0.79 mmol) were added sequentially to a solution of methanesulfonamide (0.75 g, 7.9 mmol) in methylene chloride (20 mL) at room temperature. The reaction was stirred at room temperature for 2 h and then concentrated. EtOAc was added, and the resultant mixture was washed with 1N aq. HCl solution, dried over MgSO4 and concentrated to give the desired product (1 g) to be used in the next step directly.
85% With hydrogenchloride; dmap; triethylamine In hexane; dichloromethane; water; ethyl acetate A.
N-(t-Butoxycarbonyl)Methanesulfonamide:
To a solution of 15.0 g (157.7 mmol) of methanesulfonamide, 17.6 g (173.5 mmol) of triethylamine and 1.9 g (15.8 mmol) of 4-dimethylaminopyridine in 200 mL of dichloromethane was added of 27.9 g (173.5 mmol) of di-t-butyldicarbonate in 200 mL of dichloromethane over ten minutes.
The mixture was stirred at ambient temperature for 2.25 hours and concentrated in vacuo.
The residue was dissolved in 250 mL of ethyl acetate and washed once with 200 mL of 1 N hydrochloric acid, once with 100 mL of water and once with 100 mL of saturated aqueous sodium chloride.
The organic layer was dried (MgSO4), filtered and concentrated in vacuo.
The residue was suspended in 100 mL of hexane, filtered and dried in vacuo to afford 26.1 g (85percent) of the title compound.
Analysis calculated for C7H13NO4S: percentC, 36.91; percentH, 6.71; percentN, 7.17. Found: percentC, 36.97; percentH, 6.79; percentN, 7.04.
Mass Spectrum: M+1=196.

Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 3, p. 379 - 380
[2] Patent: US2009/306057, 2009, A1, . Location in patent: Page/Page column 44
[3] Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641
[4] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286
[5] Organic Letters, 2006, vol. 8, # 21, p. 4707 - 4710
[6] Patent: WO2015/181676, 2015, A1, . Location in patent: Page/Page column 136-137
[7] Patent: WO2018/39386, 2018, A1, . Location in patent: Page/Page column 356; 357
[8] Patent: US6303816, 2001, B1,
[9] Patent: WO2008/85300, 2008, A1, . Location in patent: Page/Page column 85
[10] Patent: EP1553074, 2005, A1, . Location in patent: Page/Page column 44
[11] Patent: US2010/256092, 2010, A1, . Location in patent: Page/Page column 109
[12] Patent: US2012/316156, 2012, A1,
[13] Patent: US2014/121198, 2014, A1, . Location in patent: Paragraph 0642; 0643
[14] Patent: US6387954, 2002, B1,
  • 9
  • [ 1122-58-3 ]
  • [ 3144-09-0 ]
  • [ 24424-99-5 ]
  • [ 121-44-8 ]
  • [ 147751-16-4 ]
Reference: [1] Patent: US6358981, 2002, B1, . Location in patent: Page column 22
  • 10
  • [ 1070-19-5 ]
  • [ 3144-09-0 ]
  • [ 147751-16-4 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
  • 11
  • [ 3144-09-0 ]
  • [ 79-04-9 ]
  • [ 202658-88-6 ]
YieldReaction ConditionsOperation in experiment
94% at 65℃; for 12 h; Large scale In a 2-liter reaction flask, 1 liter of ethyl acetate and 66 grams of methylsulfonamide were added, and 109 grams of chloroacetyl chloride was gradually added; the temperature was gradually increased to 65°C for 12 hours until the end of the reaction.The reaction solution gradually cooled to 0 degree, and a large amount of white solid precipitated; it was filtered and dried to obtain 112 g of solid SLP-10b (X=Cl).Yield: 94percent.H NMR (400MHz, CDCl3): δ 4.02 (s, 2H), 3.28s, 3H)ESI/MS+(m/z):171
74% for 8 h; Heating / reflux 26.8 mol of chloroacetyl chloride and 25.5 mol of methanesulfonamide in 10.2 L of butyl acetate are slowly boiled at reflux. After 8 h, the mixture is cooled to 20° C. The precipitated solid is filtered off and stirred in 4 L of butyl acetate. The precipitated solid is dried at 50° C. in a fan-assigned drying cabinet. Yield 74percent
14 g at 125℃; for 16 h; Methane sulfonamide (10 gm) and n-butylacetate (80 mL) were charged into a 250 mL round bottom flask at 30°C. Chloroacetylchloride (21 .37 gm) was added slowly over a period of 10 minutes at 30°C. Temperature of the reaction mass was raised to 125°C and maintained reflux for 16 hours. Progress of the reaction was monitored by TLC and after completion of the reaction the mass was cooled to 20°C and stirred for 1 hour at 20°C. Reaction mass was filtered and the wet solid was washed with n- butylacetate (10 mL). The wet solid was taken into another 100 mL round bottom flask and n-butylacetate (50 mL) was added and stirred for 30 minutes at 20°C. The precipitation was filtered and the solid was suck dried. The material was dried at 45° under vacuum for 5 hours to yield 14 gm of title compound.
Reference: [1] Patent: CN106316967, 2017, A, . Location in patent: Paragraph 0063; 0108; 0109; 0110; 0111; 0112
[2] Patent: US6995262, 2006, B1, . Location in patent: Page/Page column 63
[3] Patent: WO2017/29594, 2017, A1, . Location in patent: Page/Page column 19
  • 12
  • [ 3144-09-0 ]
  • [ 1355646-97-7 ]
  • [ 1132935-63-7 ]
Reference: [1] Patent: US2012/14913, 2012, A1, . Location in patent: Page/Page column 29-30
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