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[ CAS No. 867-44-7 ] {[proInfo.proName]}

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Chemical Structure| 867-44-7
Chemical Structure| 867-44-7
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Product Details of [ 867-44-7 ]

CAS No. :867-44-7 MDL No. :MFCD00013055
Formula : C4H14N4O4S3 Boiling Point : -
Linear Structure Formula :- InChI Key :BZZXQZOBAUXLHZ-UHFFFAOYSA-N
M.W : 278.37 Pubchem ID :13347
Synonyms :
S-methyl Isothiourea (hemisulfate);(S)-Methylisothiourea sulfate;SMIT

Calculated chemistry of [ 867-44-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 4.0
Molar Refractivity : 63.09
TPSA : 242.46 Ų

Pharmacokinetics

GI absorption : Low
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) : -8.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.11
Log Po/w (XLOGP3) : -1.03
Log Po/w (WLOGP) : -3.41
Log Po/w (MLOGP) : -1.93
Log Po/w (SILICOS-IT) : -0.21
Consensus Log Po/w : -1.34

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.79
Solubility : 45.7 mg/ml ; 0.164 mol/l
Class : Very soluble
Log S (Ali) : -3.57
Solubility : 0.0742 mg/ml ; 0.000267 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.01
Solubility : 269.0 mg/ml ; 0.966 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.42

Safety of [ 867-44-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 867-44-7 ]

* 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 [ 867-44-7 ]
  • Downstream synthetic route of [ 867-44-7 ]

[ 867-44-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 867-44-7 ]
  • [ 4595-60-2 ]
  • [ 823-09-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6316 - 6321
  • 2
  • [ 141-97-9 ]
  • [ 867-44-7 ]
  • [ 6328-58-1 ]
Reference: [1] Heterocyclic Communications, 2003, vol. 9, # 4, p. 359 - 362
  • 3
  • [ 3558-68-7 ]
  • [ 867-44-7 ]
  • [ 56734-10-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, vol. 19, # 7, p. 714 - 719[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 7, p. 893 - 898
  • 4
  • [ 87-56-9 ]
  • [ 867-44-7 ]
  • [ 61727-33-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 2, p. 539 - 547
  • 5
  • [ 488-11-9 ]
  • [ 867-44-7 ]
  • [ 50593-92-5 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With triethylamine In water at 10 - 20℃; for 28 h;
Stage #2: With hydrogenchloride In water
Mucobromic acid (58.05 g, 0.225 mol) was added to a stirred solution of 2-methyl-2-thio- pseudourea sulfate (62.66 g, 0.225 mol) in water (500 mL) at r.t. The suspension was cooled to 10 °C (ice bath) and triethylamine (94.1 mL, 0.675 mol) was added dropwise over 4 h. The reaction mixture was then left to stand at r.t. for 24 h. Activated carbon (Darco G-60) was added to the now dark red / brown solution and after stirring for 10 min the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (50 mL) and the yellow precipitate was filtered off, washed with water (2 x 80 mL) and diethyl ether (2 x 100 mL), and then placed in a vacuum oven at 50 0C for 2 days to yield 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (33.13 g, 59percent) as a yellow amorphous solid. 1H NMR δ (de-DMSO, 400 MHz) 2.75 (s, 3 H), 9.20 (s, 1 H).
45% With triethylamine In water at 10 - 20℃; for 13 h; (Z)-2 , 3-d ibromo-4- oxobut-2-enoic acid (30 g, 0.116 mol) was added to a stirred solution of methyl carbamimidothioate sulfate (1.2) (32 g, 0.116 mol) in water (250 mL) at it The suspension was cooled to 10 °C (ice bath) and Et3N (48.6 mL, 0.349 mol) was addeddrop wise over 1 h. The reaction mixture was stirred at rt for 12 h. Activated carbon (10 g) was added to the now dark reddish solution and 10 mm later, the charcoal was filtered off. The filtrate was acidified with concentrated hydrochloric acid (25 mL) and the yellow precipitate was filtered off, washed with water (2 x 80 mL) and diethyl ether (2 x 100 mL), dried in vacuum to afford the title compound (13 g, 45percent yield) as a yellow solid. LC-MS:[M-H] 247.7.
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 2, p. 539 - 547
[2] Patent: WO2006/66172, 2006, A1, . Location in patent: Page/Page column 50
[3] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00283
[4] Patent: WO2014/99836, 2014, A1, . Location in patent: Page/Page column 29; 30
  • 6
  • [ 43156-48-5 ]
  • [ 867-44-7 ]
  • [ 79-22-1 ]
  • [ 43210-67-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 273 - 276
  • 7
  • [ 867-44-7 ]
  • [ 95-83-0 ]
  • [ 79-22-1 ]
  • [ 20367-38-8 ]
Reference: [1] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2221 - 2224
[2] European Journal of Medicinal Chemistry, 2009, vol. 44, # 4, p. 1794 - 1800
  • 8
  • [ 6191-97-5 ]
  • [ 867-44-7 ]
  • [ 73781-88-1 ]
Reference: [1] Patent: WO2007/55942, 2007, A2, . Location in patent: Page/Page column 63-65
  • 9
  • [ 10601-80-6 ]
  • [ 867-44-7 ]
  • [ 109-94-4 ]
  • [ 73781-88-1 ]
Reference: [1] Patent: US2009/105264, 2009, A1, . Location in patent: Page/Page column 33
  • 10
  • [ 867-44-7 ]
  • [ 92385-43-8 ]
  • [ 73781-88-1 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1986, vol. 40, # 9, p. 764 - 767
  • 11
  • [ 18780-70-6 ]
  • [ 867-44-7 ]
  • [ 24697-74-3 ]
YieldReaction ConditionsOperation in experiment
65% at 120℃; for 6 h; To a stirred solution of compound 2 (5.6g, 20mmol) in DMF (15mL) was added S-methylisothiourea hemisulfate (3) (15percent in water, 23.1g, 25mmol), the mixture was heated to reflux and stirred at 120°C for 6h. HPLC indicated the disappearance of starting material, the solvent was removed in vacuo and the residue was dissolved in water. NaHCO3 (2.31g, 27.5mmol) was added and lots of solid began to appear as the mixture stirring. The solid was collected by filtration and dried to give Leonurine (1) (4.0g, 65percent yield) as a white solid. 1H NMR (400MHz, CF3COOD): δ 7.38 (s, 2H), 4.42 (t, 2H, J=6.2Hz), 3.91 (s, 6H), 3.30 (t, 2H, J=6.7Hz), 1.89 (dt, 2H, J=13.3, 6.5Hz), 1.83–1.71 (m, 2H). lit. [18] 1H NMR (400MHz, CF3COOD): δ 7.36 (s, 2H), 4.3∼4.55 (br, 2H), 3.94 (s, 6H), 3.15∼3.45 (br, 2H), 1.75∼2.05 (br, 4H).
Reference: [1] Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1172 - 1175
  • 12
  • [ 867-44-7 ]
  • [ 90905-31-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7426 - 7432
  • 13
  • [ 867-44-7 ]
  • [ 90905-31-0 ]
  • [ 55551-49-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7426 - 7432
  • 14
  • [ 64-17-5 ]
  • [ 867-44-7 ]
  • [ 90905-31-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7426 - 7432
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7426 - 7432
  • 15
  • [ 867-44-7 ]
  • [ 90905-31-0 ]
  • [ 55551-49-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7426 - 7432
  • 16
  • [ 24424-99-5 ]
  • [ 867-44-7 ]
  • [ 107819-90-9 ]
YieldReaction ConditionsOperation in experiment
62% With sodium hydroxide; citric acid In water; <i>tert</i>-butyl alcohol E)
Preparation of N,N'-di-Boc-S-methylisothiourea
To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL).
After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL).
The organic phase was washed once with water (250 mL), three times with 1 N citric acid (250 mL) and once again with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
62% With sodium hydroxide; citric acid In water; <i>tert</i>-butyl alcohol E)
Preparation of N,N'-di-Boc-S-methylisothiourea.
To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL).
After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL).
The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
62% With sodium hydroxide; citric acid In water; <i>tert</i>-butyl alcohol E)
Preparation of N,N'-di-Boc-S-methylisothiourea
To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL).
After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL).
The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
62% With sodium hydroxide; citric acid In water; <i>tert</i>-butyl alcohol E)
Preparation of N,N'-di-Boc-S-methylisothiourea
To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL).
After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL).
The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.

Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 9, p. 1700 - 1703
[2] Patent: US5914319, 1999, A,
[3] Patent: US5705487, 1998, A,
[4] Patent: US5710130, 1998, A,
[5] Patent: US5726159, 1998, A,
[6] Patent: US5707966, 1998, A,
  • 17
  • [ 24424-99-5 ]
  • [ 867-44-7 ]
  • [ 173998-77-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 22, p. 9858 - 9866
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