22483-09-6|2,2-Dimethoxyethanamine| Ambeed

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Quality Control of [ 22483-09-6 ] Purity: 98% SDS Specification

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Product Details of [ 22483-09-6 ]

CAS No. :	22483-09-6
Formula :	C₄H₁₁NO₂
M.W :	105.14
SMILES Code :	COC(OC)CN
MDL No. :	MFCD00008135
InChI Key :	QKWWDTYDYOFRJL-UHFFFAOYSA-N
Pubchem ID :	89728

Safety of [ 22483-09-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H226-H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	3(8)
UN#:	2924
Packing Group:	Ⅲ

Computational Chemistry of [ 22483-09-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	26.22
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	44.48 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.3
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	-0.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.44
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.	-0.66
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	-0.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	0.24
Solubility	183.0 mg/ml ; 1.74 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	0.4
Solubility	262.0 mg/ml ; 2.49 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	-0.16
Solubility	72.9 mg/ml ; 0.693 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.	-7.54 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	2.0
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	1.0 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)	1.43

Application In Synthesis of [ 22483-09-6 ]

* 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 [ 22483-09-6 ]
Downstream synthetic route of [ 22483-09-6 ]

[ 22483-09-6 ] Synthesis Path-Upstream 1~3

1
[ 5500-21-0 ]
[ 22483-09-6 ]
[ 89532-38-7 ]

References: [1] Patent: WO2009/156951, 2009, A2, . Location in patent: Page/Page column 46.

2
[ 22483-09-6 ]
[ 103-80-0 ]
[ 89314-87-4 ]

References: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1496 - 1504.
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 7, p. 1871 - 1875.

3
[ 19847-12-2 ]
[ 22483-09-6 ]
[ 119165-68-3 ]

References: [1] Chemical Communications, 2015, vol. 51, # 12, p. 2425 - 2428.

[ 22483-09-6 ] Synthesis Path-Downstream 1~33

1
[ 624-83-9 ]
[ 22483-09-6 ]
[ 39799-77-4 ]

References: [1]Journal of Pharmaceutical Sciences,1981,vol. 70,p. 1322 - 1324.

2
[ 4903-09-7 ]
[ 22483-09-6 ]
[ 865660-26-0 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 486 - 494.

3
[ 50606-58-1 ]
[ 22483-09-6 ]
[ 204979-42-0 ]

References: [1]Synthetic Communications,2001,vol. 31,p. 401 - 408.

4
[ 52328-05-9 ]
[ 22483-09-6 ]
[ 1450-93-7 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 593 - 595.

5
[ 1694-06-0 ]
[ 22483-09-6 ]
1-(4-methylphenylsulfonyl)-3-(2,2-dimethoxyethyl)urea [ No CAS ]

References: [1]Polish Journal of Chemistry,2004,vol. 78,p. 547 - 551.

6
[ 119072-55-8 ]
[ 4214-79-3 ]
[ 123-38-6 ]
[ 22483-09-6 ]
2-(N-(5-chloropyridin-2-yl)-N-(2,2-dimethoxyethyl)amino)-N-tert-butylbutanamide [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4169 - 4180.

7
[ 3012-80-4 ]
[ 22483-09-6 ]
[ 854745-40-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium cyanoborohydride; acetic acid; In methanol; at 25℃; for 1h;	Example 64A; 2, 2-dimethoxy-N-[(1-methyl-lH-benzimidazol-2-yl) methyl] ethanamine; A solution of <strong>[3012-80-4]1-methyl-2-formylbenzimidazole</strong> (lg) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25C, stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHC03 and brine, and concentrated. The residue was purified by eluting with 8% methanol/dichloromethane to give 1.2 g (64%) of the title compound.

References: [1]Patent: WO2005/61487,2005,A1 .Location in patent: Page/Page column 130.

8
[ 129768-28-1 ]
[ 22483-09-6 ]
[ 877402-80-7 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: CDI (3.90 g, 24 mmol) was added to a solution of acid 4a-d (20 mmol) in anhydrous acetonitrile (50 ml). The reaction mixture was stirred and heated at 60-70C for 3-4 h, then treated with 2,2-dimethoxyethan-1-amine (2.10 g, 20 mmol) and stirred at the same temperature for additional 2-3 h. The solvent was removed by evaporation, the residue was dissolved in ethyl acetate (60 ml), treated with aqueous 1 HCl solution (3×10 ml), the organic layer was separated, dried over anhydrous Na2SO4, evaporated, and air-dried. Products 5a-d were obtained as white crystalline powders.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 20.0h;	A mixture of 500 mg (2.78 mmol) of 3-(trifiuoromethyl)-l//-pyrazole-5-carboxylic acid,0.333 mL (3.05 mmol) of aminoacetaldehyde dimethyl acetal, 588 mg (3.05 mmol) of l-(3-dimethylaminopropyl)-3-ethylcarbodiifnide hydrochloride (EDC), 510 mg (3.33 mmol) of 1-hydroxybenzotriazole (HOBT), 1.92 mL (11.1 mmol) of Af,Af-diisopropylethylamine, and 20 mL ofdichloromethane was stirred at room temperature for 20 h and then concentrated. Purification of theresidue by flash chromatography on silica gel (0-10% methanol in dichloromethane) afforded the titlecompound as a white solid. LC-MS 268 (M+l).

References: [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 1242 - 1247.
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 1242 - 1247,6.
[2]Patent: WO2006/23750,2006,A2 .Location in patent: Page/Page column 63.

9
[ 78495-65-5 ]
[ 22483-09-6 ]
2,3-dihydro-7,8-dimethoxy-6-fluoro-2-oxo-1H-3-benzazepine [ No CAS ]
N-(2,2-dimethoxyethyl)-3,4,-dimethoxy-2-fluorophenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Following the procedures outlined in Examples 1 and 2, the <strong>[78495-65-5]2-fluorohomoveratric acid</strong> is reacted with aminoacetaldehyde dimethylacetal to form N-(2,2-dimethoxyethyl)-3,4,-dimethoxy-2-fluorophenylacetamide which is ring closed with hydrochloric acid and glacial acetic acid to obtain 2,3-dihydro-7,8-dimethoxy-6-fluoro-2-oxo-1H-3-benzazepine.

References: [1]Patent: US4265890,1981,A .

10
[ 591-31-1 ]
[ 22483-09-6 ]
[ 407-25-0 ]
[ 39989-39-4 ]

Yield	Reaction Conditions	Operation in experiment
66.9 g (84%)	With hydrogenchloride; ammonia; trifluoroborane diethyl ether; In toluene;	85a. 7-Methoxy-isoquinoline Aminoacetaldehyde dimethyl acetal (81.9 mL) was added to a solution of 60.8 mL of 3-methoxy-benzaldehyde in 600 mL of toluene. The mixture was refluxed for 5 h using a Dean-Stark trap and subsequently cooled to 5 C. In a nitrogene atmosphere trifluoroacetic acid anhydride (209 mL) and borontrifluoride etherate (185 mL) were added in succession at such a rate, that the internal temperature was kept below 10 C. After stirring for 3 days at room temperature the the reaction mixture was poured on ice, 250 mL 2 N hydrochloric acid added and the organic layer extracted with 1 N hydrochloric acid. The pH value of the combined aqueous extracts was adjusted to pH 9 by adding concentrated aqueous ammonia. Extraction with ethyl acetate, followed by drying and removal of the solvent in vacuo gave 66.9 g (84%) of the title compound as a light brownish oil. EI-MS: 159 (M+).

References: [1]Patent: US6194409,2001,B1 .

11
[ 3132-99-8 ]
[ 22483-09-6 ]
[ 58794-09-5 ]
[ 63927-22-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6378 - 6382.

12
[ 4771-48-6 ]
[ 22483-09-6 ]
C₁₄H₁₈N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3780 - 3790.

13
[ 4771-49-7 ]
[ 22483-09-6 ]
C₁₄H₁₈N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3780 - 3790.

14
[ 43192-34-3 ]
[ 22483-09-6 ]
C₁₂H₁₆BrNO₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3098 - 3102.

15
[ 152628-03-0 ]
[ 22483-09-6 ]
[ 1207547-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20℃; for 6h;	Reference Example A3: 4-Methyl-6-(2-oxazolyl)-2-propylbenzimidazole [step 1] 6-Methoxycarbonyl-4-methyl-2-propylbenzimidazole (EP502314; 500 mg, 2.29 mmol) was suspended in ethanol (15 mL), 4 mol/L aqueous sodium hydroxide solution (3.1 mL) was added, and the mixture was stirred under reflux for 7 hr. The mixture was concentrated under reduced pressure, and water (20 mL) was added. Under ice-cooling, the mixture was adjusted to pH 1 with 2 mol/L hydrochloric acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, aminoacetaldehyde dimethylacetal (0.50 mL, 4.58 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (527 mg, 2.75 mmol) and 1-hydroxybenzotriazole (421 mg, 2.75 mmol) were added, and the mixture was stirred at room temperature for 6 hr. To the mixture were added saturated aqueous sodium hydrogen carbonate solution (100 mL) and chloroform (100 mL), and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 6-(2,2-dimethoxyethylcarbamoyl)-4-methyl-2-propylbenzimidazole. ESI-MS m/z; 306 (M + H)+; 1H-NMR (CDCl3, delta): 1.02 (t, J = 7.3 Hz, 3H), 1.82-1.97 (m, 2H), 2.65 (s, 3H), 2.92 (t, J= 7.3 Hz, 2H), 3.45 (s, 6H), 3.64 (t, J = 5.3 Hz, 2H), 4.52 (t, J = 5.3 Hz, 1H), 6.42 (s, 1H), 7.89 (s, 1H).

References: [1]Patent: EP2327690,2011,A1 .Location in patent: Page/Page column 83-84.

16
[ 499-05-8 ]
[ 22483-09-6 ]
[ 1357289-11-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	In water; at 65 - 100℃; for 5h;	Water (2.5 mL) and aminoacetaldehyde dimethyl acetal (756 muL, 7.0 mmol) were added to compound 14A (1.0 g, 7.1 mmol) at room temperature. The mixture was stirred at 65C for 1.5 hours and then stirred at 100C for 3.5 hours. After concentration to dryness, crystals were deposited by the addition of water (5 mL). 2-propanol (10 mL) was added thereto, followed by filtration. The crystals were washed with 2-propanol (5 mL) and through-flow-dried to obtain 0.98 g (yield: 76%) of crystals of compound 14B. 1H-NMR (CDCl3) delta: 4.56 (2H, d, J = 4.9 Hz), 5.38 (1H, t, J = 4.9 Hz), 7.16 (1H, dd, J = 7.3 Hz, 2.9 Hz), 7.26 (1H, d, J = 2.9 Hz), 8.31 (1H, d, J = 7.3 Hz).

References: [1]Patent: EP2602260,2013,A1 .Location in patent: Paragraph 0188.

17
[ 1246616-66-9 ]
[ 22483-09-6 ]
[ 1357289-08-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	In toluene; at 100℃; for 3h;	Add 10 mol of 4-oxo-3-benzyloxy-4H-pyran-2,5-dicarboxylic acid dimethyl ester obtained in Example 3 to 100 ml of toluene into a reaction flask,Then, the reaction bottle was placed in an oil bath and heated to 100 C. When refluxed, 12 mol of aminoacetaldehyde dimethyl acetal was added dropwise. After the addition, the reflux was continued for 3 h. After the reaction was completed,After cooling to room temperature, the toluene solvent was removed by rotary evaporation, and then the crude product was separated by column chromatography. The eluent was n-hexane: ethyl acetate:methanol = 12:3:2.2,5-pyridinedicarboxylic acid, 1-(2,2-dimethoxyethyl)-1,4-dihydro-4-oxo-3-benzyloxy-2,5-dimethyl ester,The yield was 91%;
88%	In methanol; for 6h;Reflux;	Aminoacetaldehyde dimethyl acetal (0.72 g, 6.9 mmol) was added dropwise to a methanol (20 mL) slurry solution of compound 12A (2.0 g, 6.3 mmol) at room temperature, and the mixture was then stirred for 6 hours under heating to reflux. After the completion of reaction, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate = 3:17 (v/v)) to obtain 2.26 g (yield: 88%) of compound 12B as a colorless oil. 1H-NMR (CDCl3) delta: 3.38 (6H, s), 3.81 (3H, s), 3.91 (2H, d, J = 4.7 Hz), 3.93 (3H, s), 4.47 (1H, t, J = 4.7 Hz), 5.29 (2H, s), 7.29-7.37 (3H, m), 7.42-7.44 (2H, m), 8.15 (1H, s). The compound 12B was dried under conditions of concentration under reduced pressure and left standing at 5C for approximately 2 months. In this case, this compound was still in an oil form and was not crystallized. As a result of various studies, however, the compound was successfully crystallized by repeating the addition of ethyl acetate and concentration and isolated as white crystals.

References: [1]Patent: CN108101838,2018,A .Location in patent: Paragraph 0042; 0043; 0044; 0045.
[2]Patent: EP2602260,2013,A1 .Location in patent: Paragraph 0179.
[3]Organic Process Research and Development,2016,vol. 20,p. 1461 - 1468.
[4]Organic Process Research and Development,2019,vol. 23,p. 565 - 570.

18
[ 1191-95-3 ]
[ 32161-30-1 ]
[ 59795-89-0 ]
[ 22483-09-6 ]
C₂₈H₃₉N₃O₆ [ No CAS ]