376347-09-0|N-(3-(Hydroxymethyl)phenyl)methanesulfonamide| Ambeed

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Quality Control of [ 376347-09-0 ] Purity: 95% SDS Specification

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Product Details of [ 376347-09-0 ]

CAS No. :	376347-09-0
Formula :	C₈H₁₁NO₃S
M.W :	201.24
SMILES Code :	CS(=O)(NC1=CC=CC(CO)=C1)=O
MDL No. :	MFCD12776133
InChI Key :	VPZIJOVNCXBFON-UHFFFAOYSA-N
Pubchem ID :	60661236

Safety of [ 376347-09-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Computational Chemistry of [ 376347-09-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	50.84
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	74.78 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.93
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	0.0
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.29
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.	0.12
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	0.2
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.51

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.23
Solubility	11.8 mg/ml ; 0.0587 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.12
Solubility	15.2 mg/ml ; 0.0756 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.6
Solubility	0.51 mg/ml ; 0.00254 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	No
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	No
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.	-7.53 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	0.0 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<1.0
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)	1.59

Application In Synthesis of [ 376347-09-0 ]

* 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 [ 376347-09-0 ]

[ 376347-09-0 ] Synthesis Path-Downstream 1~10

1
[ 93884-11-8 ]
[ 376347-09-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 1.0h;	Compound 3 To a 300 ml solution of 28.85 g (0.0945 mol) of compound 2 in THF is carefully added 5.32 g (0.140 mmol) of lithium aluminium hydride and the mixture is stirred for about 1 hr at room temperature. To the reaction mixture was added ethyl acetate and water under ice-cooling to decompose the excess of reducing agents. It was then partitioned between ethyl acetate and 2N HCI. the organic layer is washed with water and a saline, dried over MGS04, filtered and concentrated under reduced pressure to obtain a crude product. Recrystallization from methylene chloride/ether gives 22.34 g (0.0848 mol ; yield, 90%) of compound 3.

References: [1]Patent: WO2005/25557,2005,A1 .Location in patent: Page/Page column 35.

2
[ 376347-09-0 ]
[ 55512-05-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.0h;	C. 3-[(MethyIsulfonyl)amino]benzaldehyde.; [3-(Hydroxymethyl) phenyl](methylsulfonyl) amine (0.42 g, 2.08 mmol) was dissolved in dichloromethane (20 mL) followed by addition of pyridinium chlorochromate (0.67 g, 3.12 mmol). The reaction was stirred at rt for IH. Filtered crude reaction through a plug of silica gel and washed with 60% EtOAc/Hex (250 mL), removed volatiles under reduced pressure to afford the title compound (0.40 g, 2.01 mmol, 97%) as a white solid. MS (ESI) m/z 200.2 [M+l]+ [00391]
94%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.16667h;Molecular sieve;	To a 1500 ml solution of 22.06 g (83.8 MMOL) of compound 3 in methylene chloride are added 44 g of molecular sieve 4A (powder) and 32.5 g (151 MMOL) of pyridinium chlorochromate and the mixture is stirred fro 70 min at room temperature. The reaction mixture is purified by column chromatography on silica gel eluting with methylene chloride to yield 20.46 g (78.3 mmol ; yield, 94% of compound 4

References: [1]Patent: WO2008/51494,2008,A1 .Location in patent: Page/Page column 119.
[2]Patent: WO2005/25557,2005,A1 .Location in patent: Page/Page column 36.
[3]ChemMedChem,2015,vol. 10,p. 1548 - 1558.

3
[ 376347-09-0 ]
5-(benzylsulfonyl)-7-[(1R)-1-(hydroxymethyl)-2-methylpropyl]amino}[1,3]thiazolo[4,5-d]pyrimidin-2(3H)-one [ No CAS ]
N-(3-[(7-[(1R)-1-(hydroxymethyl)-2-methylpropyl]amino}-2-oxo-2,3-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl)oxy]methyl}phenyl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.3%	With sodium hydride; In 1-methyl-pyrrolidin-2-one; toluene; at 20 - 50℃; for 16.0h;	Solid sodium hydride (18 mg, 0.75 mmol) was added to a stirred solution of the product of step (d) (28.5 mg, 0.069 mmol) and N-[3-(HYDROXYMETHYL) phenyl] -methanesulfonamide (WO 01/90070) (35 mg, 0.17 mmol) in a mixture of toluene (0.2 mL) and l-methyl-2- pyrrolidinone (0.2 mL) at RT. The reaction mixture was stirred for 16 h at 50 C. After cooling to RT, the reaction mixture was quenched with water (0.1 mL) and concentrated. The residue was dissolved in DMSO (1 mL), and purified by preparative HPLC to give 4.5 mg (14.3%) of the title compound as an off-white solid. MS (ESI+) m/z 454 [M+H] +.

References: [1]Patent: WO2005/33115,2005,A1 .Location in patent: Page/Page column 46.

4
[ 32087-05-1 ]
[ 376347-09-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 20℃;	B. [3-(Hydroxymethyl)phenyl](methylsulfonyl)amine.; Methyl 3-[(methylsulfonyl)amino] benzoate (1.2 g, 5.23 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL) and cooled to -78 0C. A solution of lithium aluminum hydride (2.0M, 5.23 mL, 10.46 mmol) was added via syringe and allowed to slowly warm to rt. The reaction was quenched with methanol and the crude product adsorbed onto silica gel. Flash chromatography (80% EtOAc in Hexanes) afforded the title compound (0.85 g, 4.22 mmol, 81%) as a white solid. MS (ESI) m/z 202.2.1 [M+ 1]+.

References: [1]Patent: WO2008/51494,2008,A1 .Location in patent: Page/Page column 119.
[2]ChemMedChem,2015,vol. 10,p. 1548 - 1558.

5
[ 4518-10-9 ]
[ 376347-09-0 ]