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[ CAS No. 173998-77-1 ] {[proInfo.proName]}

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Chemical Structure| 173998-77-1
Chemical Structure| 173998-77-1
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Product Details of [ 173998-77-1 ]

CAS No. :173998-77-1 MDL No. :MFCD11519419
Formula : C7H14N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 190.26 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 173998-77-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.46
TPSA : 87.48 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.01
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 1.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.79
Solubility : 3.12 mg/ml ; 0.0164 mol/l
Class : Very soluble
Log S (Ali) : -3.19
Solubility : 0.122 mg/ml ; 0.00064 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.43
Solubility : 7.15 mg/ml ; 0.0376 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.28

Safety of [ 173998-77-1 ]

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 [ 173998-77-1 ]

* 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 [ 173998-77-1 ]
  • Downstream synthetic route of [ 173998-77-1 ]

[ 173998-77-1 ] Synthesis Path-Upstream   1~8

  • 1
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  • [ 173998-77-1 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 14 h; Inert atmosphere Example 29
Synthesis of ZA-G-Nap Conjugate 46 (FIG. 22)
Compound 60
To a solution of S-methylisothiourea hemisulfate salt (1085 mg, 7.80 mmol) and NaHCO3 (655 mg, 7.80 mmol) in H2O (15 mL) and THF (15 mL) was added (Boc)2O (1283 mg, 5.88 mmol) dropwise.
The mixture was stirred at room temperature under argon for 14 h, and then concentrated under reduced pressure.
The residue was partitioned between EtOAc and H2O.
The organic phase was dried over MgSO4, filtered, and purified by silica gel chromatography (EtOAc/hexane=1:4) to afford the product of tert-butyl[imino(methylthio)methyl]carbamate (1104 mg, 99percent). C7H14N2O2S; white solid; 1H NMR (CDCl3, 400 MHz) δ 2.39 (3H, s), 1.45 (9H, s); 13C NMR (CDCl3, 100 MHz) δ 172.3, 160.4, 79.1, 27.5, 12.7; HRMS (ESI) calcd for C7H15N2O2S: 191.0854, found: m/z 191.0848 [M+H]+.
94% With sodium hydroxide In dichloromethane; water at 0℃; for 6.33333 h; Preparation C; N-Boc-S-methylisothiourea; Step C (1); To a rapidly stirred suspension of S-Methylisothiourea hemisulfate (60.8 g, 0.437 mol) in CH2Cl2 (600 mL) was added 2N NaOH (300 mL, 0.6 mol). This mixture was cooled to 0° C. on an ice bath, and a solution of di-tert-butyl dicarbonate (43.2 g, 0.198 mol) was added dropwise over 6 h. Upon completion of the addition, the mixture was stirred an additional 20 min, diluted with 1 L of CH2Cl2 and the phases were separated. The organic portion was washed with water (2.x.500 ml) and dried over Na2SO4. Filtration and concentration provided the desired N-Boc-S-methylisothiourea as a white solid (35.5 g, 0.187 mol, 94percent yield based on Boc2O).
94% With sodium hydroxide In dichloromethane at 0℃; for 6 h; Preparation A; tert-Butyl methylthiocarbonoimidoylcarbamate; To a rapidly stirred suspension of S-methylisothiourea hemisulfate (60.8 g, 0.437 mol) in CH2Cl2 (600 mL) was added 2N NaOH (300 mL, 0.6 mol). This was cooled to 0° C. on an ice bath, and a solution of di-tert-butyl dicarbonate (43.2 g, 0.198 mol) was added dropwise over 6 h. Upon completion of the addition, the mixture was stirred an additional 20 min, diluted with IL CH2Cl2 and the phases were separated. The organic portion was washed with water (2.x.500 ml) and dried over Na2SO4. Filtration and concentration provided the desired mono-N-Boc-S-methylisothiourea as a white solid (35.5 g, 0.187 mol, 94percent yield based on Boc2O).
94% With sodium hydroxide In dichloromethane; water at 0℃; for 6.33333 h; N-Boc-S-methylisothiourea
To a rapidly stirred suspension of S-Methylisothiourea hemisulfate (60.8 g, 0.437 mol) in CH2Cl2 (600 mL) was added 2N NaOH (300 mL, 0.6 mol).
This mixture was cooled to 0° C. on an ice bath, and a solution of di-tert-butyl dicarbonate (43.2 g, 0.198 mol) was added dropwise over 6 h.
Upon completion of the addition, the mixture was stirred an additional 20 min, diluted with 1 L of CH2Cl2 and the phases were separated.
The organic portion was washed with water (2*500 ml) and dried over Na2SO4.
Filtration and concentration provided the desired N-Boc-S-methylisothiourea as a white solid (35.5 g, 0.187 mol, 94percent yield based on Boc2O).

Reference: [1] Patent: US2013/274229, 2013, A1, . Location in patent: Paragraph 0304
[2] Patent: US2007/49589, 2007, A1, . Location in patent: Page/Page column 12
[3] Patent: US2008/262055, 2008, A1, . Location in patent: Page/Page column 6
[4] Patent: US2007/232581, 2007, A1, . Location in patent: Page/Page column 7
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 21, p. 9208 - 9223,16
[6] Journal of Medicinal Chemistry, 2012, vol. 55, # 21, p. 9208 - 9223
[7] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1540 - 1543[8] Angew. Chem., 2016, vol. 128, # 4, p. 1564 - 1568,5
  • 2
  • [ 24424-99-5 ]
  • [ 14527-26-5 ]
  • [ 173998-77-1 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In dichloromethane at 0℃; for 6.33333 h; To a rapidly stirred suspension of S-Methylisothiourea hemisulfate (60.8 g, 0.437 mol) in CH2Cl2 (600 mL) was added 2N NaOH (300 mL, 0.6 mol).
This mixture was cooled to 0° C. on an ice bath, and a solution of di-tert-butyl dicarbonate (43.2 g, 0.198 mol) was added dropwise over 6 h.
Upon completion of the addition, the mixture was stirred an additional 20 min, diluted with IL of CH2Cl2 and the phases were separated.
The organic portion was washed with water (2*500 ml) and dried over Na2SO4.
Filtration and concentration provided the desired N-Boc-S-methylisothiourea as a white solid (35.5 g, 0.187 mol, 94percent yield based on Boc2O).
Reference: [1] Patent: US2007/232679, 2007, A1, . Location in patent: Page/Page column 8-9
  • 3
  • [ 24424-99-5 ]
  • [ 2986-19-8 ]
  • [ 173998-77-1 ]
  • [ 322474-21-5 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine; sodium hydroxide In dichloromethane at 0℃; for 4 h; CH2Cl2 (5 ml) and triethylamine (TEA) (250 l, 1.79mmol) were added to a rapidly stirred solution of Smethylisothioureahemisulfate (500 mg, 3.59 mmol) inNaOH 1N (2.5 ml). The mixture was cooled to T=0°C on an ice bath, and a solution of di-tert-butyl dicarbonate (783.5mg, 3.59 mmol) in CH2Cl2 (2 ml) was added dropwise over 3h. Upon completion of the addition, the mixture was stirredan additional hour, diluted with 1 mL of CH2Cl2, and HCl 1Nwas added until pH 4. The organic layer was extracted withacidic water, and the aqueous layer was separated from theorganic phase and neutralized with NaOH 1N; CH2Cl2 (1 ml)was added and the aqueous phase was extracted twice. Theorganic layers were separated, dried over sodium sulfate,filtered and concentrated under reduced pressure. Diethylether was added and the solvent was evaporated under vacuumtwice. The compound purity was verified by HPLCanalysis as described above. The qualitative analysis of theproduct was finally confirmed by ESI-MS. The product wasthen used directly in the next step. (377 mg, 55 percent)1H NMR (200 MHz, DMSO-d6): 1.39 (s, 9H), 2.45 (s,3H).13C NMR (50 MHz, DMSO-d6): 13.8, 27.8, 79.2, 157.3,161.4.ESI-MS m/z =191 [M+H] +
Reference: [1] Medicinal Chemistry, 2018, vol. 14, # 4, p. 1 - 7
  • 4
  • [ 24424-99-5 ]
  • [ 4338-95-8 ]
  • [ 173998-77-1 ]
YieldReaction ConditionsOperation in experiment
24 g With triethylamine In dichloromethane at 20℃; S-methylisothiourea hydroiodide (28 g) and triethylamine (18 mL) were dissolved in dichloromethane (250 mL) followed by addition of di-tert-butyl dicarbonate (28 mL). After stirring the reaction mixture at room temperature overnight, water was added and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (24 g).
Reference: [1] Patent: JP2017/214315, 2017, A, . Location in patent: Paragraph 0131; 0133
  • 5
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  • [ 173998-77-1 ]
  • [ 322474-21-5 ]
Reference: [1] Synthesis, 2012, vol. 44, # 21, p. 3387 - 3391,5
[2] Synthesis (Germany), 2012, vol. 44, # 21, p. 3387 - 3391
  • 6
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  • [ 173998-77-1 ]
Reference: [1] Patent: US6034067, 2000, A,
  • 7
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  • [ 867-44-7 ]
  • [ 173998-77-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 22, p. 9858 - 9866
  • 8
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Reference: [1] ChemMedChem, 2011, vol. 6, # 9, p. 1727 - 1738
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