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CAS No. : | 173998-77-1 | MDL No. : | MFCD11519419 |
Formula : | C7H14N2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 190.26 | Pubchem ID : | - |
Synonyms : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.28 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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] + |
Yield | Reaction Conditions | Operation 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). |
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