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[ CAS No. 599-91-7 ] {[proInfo.proName]}

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Chemical Structure| 599-91-7
Chemical Structure| 599-91-7
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Product Details of [ 599-91-7 ]

CAS No. :599-91-7 MDL No. :MFCD00059244
Formula : C10H14O3S Boiling Point : -
Linear Structure Formula :- InChI Key :JTTWNTXHFYNETH-UHFFFAOYSA-N
M.W : 214.28 Pubchem ID :69035
Synonyms :

Calculated chemistry of [ 599-91-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.2
TPSA : 51.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 2.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.432 mg/ml ; 0.00201 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.184 mg/ml ; 0.000859 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.65
Solubility : 0.0475 mg/ml ; 0.000222 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.45

Safety of [ 599-91-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 599-91-7 ]

* 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 [ 599-91-7 ]
  • Downstream synthetic route of [ 599-91-7 ]

[ 599-91-7 ] Synthesis Path-Upstream   1~12

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YieldReaction ConditionsOperation in experiment
90%
Stage #1: With potassium phosphate monohydrate; bis(trichloromethyl) carbonate In dichloromethane at 0 - 5℃; for 0.0833333 h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 0.333333 h;
Stage #3: With trimethylamine hydrochloride In dichloromethane at 20℃; for 0.5 h;
A thermometer in 100 mL 3-neck flask and stirred insert the dichloromethane 20 mL and using an ice-bath the inner temperature of 0 to 5°C. Here para-toluenesulfonic acid monohydrate 380.44 mg (2.0 mmole) and bis (trichloromethyl) carbonate, 236mg (0.80 mmole, 0.40 molbae) and tribasic potassium monohydrate (K3PO4*H 2O), 1.38 G (6 mmole, 3 moles) in that order, followed by stirring for 5 minutes.It is observed that when two drops of triethylamine (about 20 mg, 0.10 mole ratio) are added thereto, bubbles are generated in the reactor.After that, the ice-bath is removed and the temperature is raised to room temperature. The mixture is further stirred for 20 minutes.The reaction was completed by TLC analysis when 120.2 mg (2.0 mmole) of n-propyl alcohol, 202.4 mg (2.0 mmole) of triethylamine and 13.1 mg (0.2 mmole) of trimethylamine hydrochloride were added in this order and stirred at room temperature for 30 minutes You can check.After completion of the reaction, the reaction mixture was filtered and washed with 5 mL of dichloromethane to remove unreacted salts. The resulting solution was evaporated to dryness under reduced pressure to obtain 386 mg of a target compound, a tosylate derivative (yield: 90percent).
Reference: [1] Patent: KR2015/67792, 2015, A, . Location in patent: Paragraph 0026; 0027
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YieldReaction ConditionsOperation in experiment
95% With triethylamine In dichloromethane at 5 - 22℃; for 12.5 h; Industry scale [00263] EXAMPLE 16 - Industrial scale preparation of propyl tosylate:; A 100 L glass, jacketed reactor was charged with 1-propanol (2.098 kg; 34.9 mol), triethylamine (4.585 kg; 45.3 mol; 1.3 equivalents) and DCM (20.1 L). The mixture was cooled to a temperature of about 5C to 15C and cautiously charged with a solution of /Moluenesulfonyl chloride (6 kg; 31.47 mol; 0.9 equivalents) in DCM (10.5 L) over 30 minutes. Once the addition was complete, the mixture was warmed to a temperature of about 18C to 22C and stirred for 12 hours. The reaction mixture was assayed by 1H NMR (in CDCI3) and deemed complete. HCl (6 N; 2.98 L) was cautiously charged while maintaining the temperature below 25C. The aqueous phase was removed, and the organic phase was washed 2 X with water (21 L each wash), dried with MgSC>4, and filtered over Celite.(R).. The filtered solids were then washed with DCM (4 L) and concentrated to a residue. The residue was dissolved in heptane and concentrated again to afford a final propyl tosylate product (6.385 kg, 95percent yield).
95% With triethylamine In dichloromethane at 5 - 22℃; for 12.5 h; Industry scale EXAMPLE 20Industrial scale preparation of propyl tosylate[00184] A 100 L glass, jacketed reactor was charged with 1-propanol (2.098 kg;34.9 mol), triethylamine (4.585 kg; 45.3 mol; 1.3 equivalents) and DCM (20.1 L). The mixture was cooled to a temperature of about 5° C to 15° C and cautiously charged with a solution of p-toluenesulfonyl chloride (6 kg; 31.47 mol; 0.9 equivalents) in DCM (10.5 L) over 30 minutes. Once the addition was complete, the mixture was warmed to a temperature of about 18° C to 22° C and stirred for 12 hours. The reaction mixture was assayed by NMR (in CDCI3) and deemed complete. HC1 (6 N; 2.98 L) was cautiously charged while maintaining the temperature below 25° C. The aqueous phase was removed, and the organic phase was washed 2 X with water (21 L each wash), dried with MgSC4, and filtered over Celite.(R).. The filtered solids were then washed with DCM (4 L) and concentrated to a residue. The residue was dissolved in heptane and concentrated again to afford a final propyl tosylate product (6.385 kg, 95percent yield).
Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 9, p. 2125 - 2133
[2] Patent: WO2010/22140, 2010, A1, . Location in patent: Page/Page column 101
[3] Patent: WO2011/109596, 2011, A1, . Location in patent: Page/Page column 52
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 16, p. 6228 - 6239
[5] Organic Letters, 2009, vol. 11, # 8, p. 1757 - 1759
[6] Tetrahedron Letters, 2009, vol. 50, # 10, p. 1117 - 1121
[7] Chemische Berichte, 1925, vol. 58, p. 1322
[8] Chemische Berichte, 1921, vol. 54, p. 1541
[9] Journal of the American Chemical Society, 1925, vol. 47, p. 522
[10] Monatshefte fuer Chemie, 1951, vol. 82, p. 452,455,460,464
[11] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 3, p. 459 - 473
[12] Journal of the American Chemical Society, 2004, vol. 126, # 42, p. 13582 - 13583
[13] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1464 - 1473
[14] Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3904 - 3907
[15] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 263 - 273
[16] Journal of Physical Organic Chemistry, 2018, vol. 31, # 2,
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Reference: [1] RSC Advances, 2015, vol. 5, # 35, p. 27439 - 27442
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  • [ 143885-02-3 ]
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Reference: [1] Heteroatom Chemistry, 2004, vol. 15, # 3, p. 193 - 198
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 8, p. 4674 - 4680
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Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, p. 681 - 685
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Reference: [1] Journal of Physical Organic Chemistry, 2018, vol. 31, # 2,
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Reference: [1] Chemische Berichte, 1930, vol. 63, p. 678,685
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Reference: [1] Journal of Organic Chemistry, 1971, vol. 36, # 4, p. 532 - 540
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 7, p. 2710 - 2718
[2] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 7, p. 2710 - 2718
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 7, p. 2710 - 2718
[2] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 7, p. 2710 - 2718
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YieldReaction ConditionsOperation in experiment
51%
Stage #1: With N-ethyl-N,N-diisopropylamine In propan-1-ol at 95℃; for 18 h; Inert atmosphere
Stage #2: With hydrogenchloride In ethanol at 0 - 5℃;
The resulting solids were dried under high vacuum for 2 h and then taken up in 50 mL of ethanol and cooled to between 0 and 5° C.
With continuous stirring, concentrated HCl (45 mL) was slowly added to the reaction while maintaining the temperature at between 0 and 5° C., and the mixture was stirred for an additional 15 min.
Methyl t-butyl ether (MTBE, 270 mL) was added to mixture, and stirring was continued for additional 1.5 h at this temperature.
The mixture was filtered, washed twice with an MTBE/ethanol solution (2:1; 2*70 mL), and dried under high vacuum at room temperature for 18 h to afford 38.5 g of the di-hydrochloride salt of (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (Yield: 51percent). MS calculated for C10H17N3S: 211.11. found: 212.1 [M+H]+.
Reference: [1] Patent: US2013/59801, 2013, A1, . Location in patent: Paragraph 0317-0318
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