38993-84-9|(1-Methyl-1H-imidazol-5-yl)methanol| Ambeed

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Quality Control of [ 38993-84-9 ] Purity: 97% SDS Specification

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Product Details of [ 38993-84-9 ]

CAS No. :	38993-84-9
Formula :	C₅H₈N₂O
M.W :	112.13
SMILES Code :	CN1C=NC=C1CO
MDL No. :	MFCD02179522
InChI Key :	PXGQMYCEAWZJJF-UHFFFAOYSA-N
Pubchem ID :	2773450

Safety of [ 38993-84-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 38993-84-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	5
Fraction Csp3	0.4
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	29.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.12
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	-0.84
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.24
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.	-0.94
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	0.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.4
Solubility	44.4 mg/ml ; 0.396 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.	0.52
Solubility	373.0 mg/ml ; 3.32 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly 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	-0.57
Solubility	30.4 mg/ml ; 0.271 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.	-7.58 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	1.0
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)	1.37

Application In Synthesis of [ 38993-84-9 ]

* 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 [ 38993-84-9 ]

[ 38993-84-9 ] Synthesis Path-Downstream 1~35

1
[ 39021-62-0 ]
[ 38993-84-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 0.333333h;	3-Methyl-3H-imidazole-4- carbaldehyde (10) (4.0 g, 15 mmol) was suspended in THF (10 mL), and the resulting solution cooled to 0°C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added portion wise over 10 minutes, and the resulting suspension stirred for a further 10 minutes. Excess hydride was quenched by the addition of solid Na2SO4-IOH2O (~1 g) in large portions with vigorous stirring. Additional THF was added as needed to prevent solidification of the resulting slurry. The resulting suspension was stirred for a further hour, and then filtered to remove the sulfate salts, and the solvent was removed under reduced pressure to provide the title alcohol (1.3 g, 80percent). 1H NMR (400 MHz, ^-MeOH): delta 7.57 (s, IH), 6.89 (s, IH), 4.58 (s, 2H), 372 (s, 3H). 13C NMR (100 MHz, ^-MeOH): delta 140.1, 132.7, 128.1, 31.9, 31.0.

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5710 - 5727.
[2]Patent: WO2006/102159,2006,A2 .Location in patent: Page/Page column 22.
[3]Journal of the American Chemical Society,1949,vol. 71,p. 2444,2447.

2
[ 38993-84-9 ]
[ 89180-90-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane;	(1 -Methyl- 1 H-imidazol-5-yl)methanol was converted to the corresponding alkyl chloride by reaction with thionyl chloride in DCM. N-[1 -(Fluoromethyl)cyclopropyl]-3- [(1 -methylpyrazol-4-yl)methyl]-2,4-dioxo-1 1H-quinazoline-6-sulfonamide (100 mg, 0.260 mmol), the alkyl chloride (37 mg, 0.286 mmol) and potassium carbonate (43 mg, 0.312 mmol) in DMF was conventionally heated to 70 °C for 4 h. Usual work-up afforded the desired product (37 mg, 0.074 mmol, 28percent) as an off-white powder.
	With thionyl chloride;N,N-dimethyl-formamide; at 20℃; for 2h;Sonographic reaction;	Thionyl chloride (3.88mL, 53.5mmol) was added dropwise to 3-methyl-3H-imidazol-4- yl)-methanol (o.3g, 2.68mmol). The reaction was sonicated briefly, treated with DMF (1 drop) and allowed to stir at ambident temperature for 1 h. The volatiles were removed and the residue treated with diethyl ether. The diethyl ether was decanted and the procedure repeated 3 times. The semi-solid residue was treated with dimethylamine in THF (6.69mL, 13.38mmol) followed DMF (1 mL). The reaction was heated in a CEM microwave reactor at 8O0C for 30 minutes, treated with acetic acid (1 ml_) and purified by SCX cartridge to give the title compound (0.18g, 1.22mmol). LC-MS (method 1): R, 2.9 min, m/z 140 [MH]+.
	With thionyl chloride;N,N-dimethyl-formamide; for 0.5h;	DMF (1 drop) was added to a slowly stirred solution of (3-methyl-3H-imidazol-4-yl)-methanol (11) (1.8 g, 16 mmol) dissolved in thionyl chloride (12 mL). After 30 minutes the solvent was removed under reduced pressure, and the resulting solid triturated with diethyl ether (20 mL). The resulting semi-solid was dried over night under vacuum, and used without further purification. 1H NMR (400 MHz, CI4-MQOR): delta 8.98 (s, IH), 7.63 (s, IH), 4.85 (s, 2H), 3.90 (s, 3H). 13C NMR (100 MHz, d4- MeOH): delta 138.3, 132.6, 120.5, 34.5, 33.9.

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 2444,2447.
[2]Angewandte Chemie - International Edition,2005,vol. 44,p. 4903 - 4906.
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 5710 - 5727.
[4]Patent: WO2016/92326,2016,A1 .Location in patent: Paragraph 00825.
[5]Patent: WO2008/23157,2008,A1 .Location in patent: Page/Page column 94.
[6]Patent: WO2006/102159,2006,A2 .Location in patent: Page/Page column 22.

3
[ 50-00-0 ]
[ 32673-41-9 ]
[ 38993-84-9 ]

References: [1]Zhurnal Obshchei Khimii,1947,vol. 17,p. 1718,1724.
Chem.Abstr.,1948,p. 2967.

4
[ 822-55-9 ]
[ 17289-25-7 ]
[ 38993-84-9 ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 4950,4951, 4952.

5
[ 17289-20-2 ]
[ 38993-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; formaldehyd; In water;	EXAMPLE 8 Preparation of 1-methyl-5-hydroxymethylimidazole To a suspension of 1.4 g (0.01 mol) of 1-methyl-5-carbmethoxyimidazole in 5 ml of water is added 0.8 g (0.02 mol) of sodium hydroxide, and the mixture was heated to reflux for 2 hours. To the mixture is added 4 ml of ~37percent aqueous formaldehyde solution, and the resultant mixture is heated at 80-90 for 2 hours. After completion of the reaction, the solvent is stripped off and the residue is extracted with ethyl acetate. The ethyl acetate extract was concentrated to give 1-methyl-5-hydroxymethylimidazole as a solid, m.p. 112°-114° C.

References: [1]Synthesis,1994,p. 247 - 248.
[2]Journal of the American Chemical Society,1949,vol. 71,p. 2444,2447.
[3]Journal of medicinal chemistry,1998,vol. 41,p. 5265 - 5271.
[4]Journal of the American Chemical Society,1949,vol. 71,p. 2444,2447.
[5]Patent: US4292431,1981,A .

6
[ 38993-84-9 ]
[ 98-88-4 ]
[ 158629-15-3 ]

References: [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 381 - 388.

7
[ 38993-84-9 ]
[ 874-60-2 ]
[ 158629-17-5 ]

References: [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 381 - 388.

8
[ 38993-84-9 ]
[ 122-01-0 ]
[ 158629-16-4 ]

References: [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 381 - 388.

9
[ 38993-84-9 ]
[ 100-07-2 ]
[ 158629-18-6 ]

References: [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 381 - 388.

10
[ 38993-84-9 ]
[ 122-04-3 ]
[ 158629-19-7 ]

References: [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 381 - 388.

11
[ 38993-84-9 ]
[ 39021-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese dioxide; In 1,4-dioxane;	EXAMPLE 32C 1-methyl-1H-imidazole-5-carbaldehyde A solution of Example 32B (2.3 g, 20 mmol) in dioxane (100 mL), was treated with manganese dioxide (17.3 g, 200 mmol), heated to reflux for 16 hours, cooled to room temperature, filtered through a pad of diatomaceous earth (Celite.(R).), and concentrated to provide the desired product of sufficient purity for subsequent use without further purification. 1H NMR (300 MHz, CDCl3) delta 9.77 (d, 1H), 7.79 (s, 1H), 7.62 (s, 1H), 3.95 (d, 3H).

References: [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 695 - 703.
[2]Journal of Organic Chemistry,1993,vol. 58,p. 1159 - 1166.
[3]Bollettino Chimico Farmaceutico,2003,vol. 142,p. 251 - 254.
[4]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 1345 - 1354.
[5]Journal of Organic Chemistry,2001,vol. 66,p. 8252 - 8256.
[6]Synthesis,1994,p. 247 - 248.
[7]Archiv der Pharmazie,2002,vol. 335,p. 69 - 76.
[8]Patent: US2002/19527,2002,A1 .
[9]Archives of Pharmacal Research,2013,vol. 36,p. 436 - 447.

12
[ 41806-40-0 ]
[ 38993-84-9 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 1159 - 1166.

13
[ 143122-18-3 ]
[ 38993-84-9 ]

References: [1]Archives of Pharmacal Research,2013,vol. 36,p. 436 - 447.
[2]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 1345 - 1354.
[3]Archiv der Pharmazie,2002,vol. 335,p. 69 - 76.
[4]Arzneimittel-Forschung/Drug Research,2002,vol. 52,p. 537 - 542.
[5]European Journal of Organic Chemistry,2017,vol. 2017,p. 695 - 703.
[6]Journal of Organic Chemistry,2001,vol. 66,p. 8252 - 8256.
[7]Journal of Organic Chemistry,1993,vol. 58,p. 1159 - 1166.
[8]Bollettino Chimico Farmaceutico,2003,vol. 142,p. 251 - 254.
[9]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 81 - 89.

14
[ 141524-73-4 ]
[ 38993-84-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1784 - 1790.

15
[ 38993-84-9 ]
[ 34798-95-3 ]
6-(3-methyl-3H-imidazol-4-ylmethoxy)-9H-purin-2-ylamine [ No CAS ]

References: [1]Journal of medicinal chemistry,1998,vol. 41,p. 5265 - 5271.

16
[ 38993-84-9 ]
[ 5416-93-3 ]
(4-methoxy-phenyl)-carbamic acid 3-methyl-3H-imidazol-4-ylmethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2237 - 2242.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 32B (1-methyl-1H-imidazol-5-yl)methanol A solution of Example 32A (50 g, 0.35 mol) in ethanol (500 mL) was treated with Raney.(R). nickel (500 g), heated to reflux for 1 hour, cooled to room temperature, filtered, and concentrated to provide the desired product of sufficient purity for subsequent use without further purification. MS (DCI/NH3) m/z 113 (M+H)+; 1H NMR (400 MHz, DMSO-d6) delta 7.50 (s, 1H), 6.75 (s, 1H), 5.01 (s, 1H), 4.41 (s, 2H), 3.59 (s, 3H).

18
[ 38993-84-9 ]
[ 4548-45-2 ]
2-(3-methyl-3H-imidazol-4-ylmethoxy)-5-nitro-pyridine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1867 - 1870.

19
[ 98-91-9 ]
[ 38993-84-9 ]
[ 163009-15-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 465 - 475.

20
[ 38993-84-9 ]
[ 2746-25-0 ]
[ 384821-12-9 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8252 - 8256.

21
[ 38993-84-9 ]
[ 74-88-4 ]
5-methoxymethyl-1-methyl-1H-imidazole [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8252 - 8256.

22
[ 38993-84-9 ]
[ 85012-71-1 ]

References: [1]Archiv der Pharmazie,2002,vol. 335,p. 69 - 76.
[2]Arzneimittel-Forschung/Drug Research,2002,vol. 52,p. 537 - 542.

23
[ 38993-84-9 ]
[ 76-05-1 ]
[ 480445-51-0 ]
8-(4-bromo-benzyl)-3-isobutyl-1-(3-methyl-3H-imidazol-4-ylmethyl)-3,7-dihydro-purine-2,6-dione [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1973 - 1976.

24
3-methyl-3H-imidazole-4-carboxaldehyde trifluoromethanesulfonate [ No CAS ]
[ 38993-84-9 ]