107819-90-9|1,3-Di-Boc-2-methylisothiourea| Ambeed

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Quality Control of [ 107819-90-9 ] Purity: 97% SDS Specification

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Product Details of [ 107819-90-9 ]

CAS No. :	107819-90-9
Formula :	C₁₂H₂₂N₂O₄S
M.W :	290.38
SMILES Code :	CS/C(NC(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O
MDL No. :	MFCD00239356

Safety of [ 107819-90-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 107819-90-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	8
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	77.3
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	102.29 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.36
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.17
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.6
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.56
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.41
Solubility	0.112 mg/ml ; 0.000387 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.49
Solubility	0.000946 mg/ml ; 0.00000326 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.32
Solubility	1.4 mg/ml ; 0.00483 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.48 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	3.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	4.25

Application In Synthesis of [ 107819-90-9 ]

* 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.

Downstream synthetic route of [ 107819-90-9 ]

[ 107819-90-9 ] Synthesis Path-Downstream 1~37

1
[ 98433-13-7 ]
[ 107819-90-9 ]
[ 107819-91-0 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 1700 - 1703.

2
[ 24424-99-5 ]
[ 867-44-7 ]
[ 107819-90-9 ]

Yield	Reaction Conditions	Operation in experiment
42 g (62%)	With sodium hydroxide; citric acid; In water; tert-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.
42 g (62%)	With sodium hydroxide; citric acid; In water; tert-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.
42 g (62%)	With sodium hydroxide; citric acid; In water; tert-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.

42 g (62%)

With sodium hydroxide; citric acid; In water; tert-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.

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 1700 - 1703.
[2]Patent: US5914319,1999,A .
[3]Patent: US5705487,1998,A .
[4]Patent: US5710130,1998,A .
[5]Patent: US5726159,1998,A .

3
[ 2640-58-6 ]
[ 107819-90-9 ]
[ 83585-01-7 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 6541 - 6542.

4
[ 107819-90-9 ]
[ 332882-82-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In methanol;	Step B Tert-butyl (2E)-3-amino-2-aza-3-[(tert-butoxy)carbonylamino]prop-2-enoate Tert-butyl (2Z)-2-aza-3-[(tert-butoxy)carbonylamino]-3-methylthioprop-2-enoate was dissolved in MeOH (0.1M) followed by addition of 1N NH4OH (5 eq). After stirring overnight the solution was concentrated in vacuo to afford a colorless solid. EI-MS m/z 411 (M+H)+.

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 2300 - 2309.
[2]Tetrahedron Letters,1994,vol. 35,p. 977 - 980.
[3]Patent: US6514964,2003,B1 .

5
[ 107819-90-9 ]
[ 257292-16-3 ]
[ 257292-17-4 ]

References: [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2487 - 2497.

6
[ 110-85-0 ]
[ 876-08-4 ]
[ 107819-90-9 ]
MeO-poly(ethylene glycol) [ No CAS ]
[ 220213-06-9 ]

References: [1]Synlett,1998,p. 1423 - 1425.

7
[ 505-66-8 ]
[ 876-08-4 ]
[ 107819-90-9 ]
MeO-poly(ethylene glycol) [ No CAS ]
[ 220213-07-0 ]

References: [1]Synlett,1998,p. 1423 - 1425.

8
[ 876-08-4 ]
[ 7144-05-0 ]
[ 107819-90-9 ]
MeO-poly(ethylene glycol) [ No CAS ]
[ 220213-05-8 ]

References: [1]Synlett,1998,p. 1423 - 1425.

9
[ 67-56-1 ]
[ 107819-90-9 ]
PEG supported 3-nitro-4-N-(3-aminopyrrolidine)benzoate [ No CAS ]
C₂₃H₃₃N₅O₈ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1517 - 1520.

10
[ 67-56-1 ]
[ 107819-90-9 ]
PEG supported 3-nitro-4-(N-piperazine)benzoate [ No CAS ]
4-[4-(tert-butoxycarbonylamino-tert-butoxycarbonylimino-methyl)-piperazin-1-yl]-3-nitro-benzoic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1517 - 1520.

11
[ 67-56-1 ]
[ 107819-90-9 ]
PEG supported 3-nitro-4-(N-homopiperazine)benzoate [ No CAS ]
4-[4-(tert-butoxycarbonylamino-tert-butoxycarbonylimino-methyl)-[1,4]diazepan-1-yl]-3-nitro-benzoic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1517 - 1520.

12
[ 107819-90-9 ]
[ 195195-99-4 ]
C₂₆H₃₄F₂N₄O₈ [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 130 - 133.

13
[ 107819-90-9 ]
[ 195196-01-1 ]
[ 322474-26-0 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 130 - 133.

14
[ 107819-90-9 ]
[ 322474-19-1 ]
(2-oxo-3-trifluoromethyl-piperidin-3-yl)-carbamic acid benzyl ester [ No CAS ]
C₂₆H₃₇F₃N₄O₈ [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 130 - 133.

15
[ 107819-90-9 ]
C₂₃H₂₃N₃O₃ [ No CAS ]
[ 288621-81-8 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2759 - 2769.

16
[ 107819-90-9 ]
[ 221236-09-5 ]
3-amidinobenzoyl-D-phenylglycine 1-(1,3-bis-tert-butylcarbonyl amidine)-4-piperidinylethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1221 - 1232.

17
[ 107819-90-9 ]
1-(6-amino-hexyl)-6-(5-amino-pentyloxy)-1H-indole-2-carboxylic acid; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]
[ 502937-00-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3849 - 3858.

18
[ 123-75-1 ]
[ 107819-90-9 ]
[ 207857-31-6 ]