3171-46-8|3,5-Dimethyl-1,2-benzenediamine| Ambeed

CAS No. :	3171-46-8
Formula :	C₈H₁₂N₂
M.W :	136.19
SMILES Code :	NC1=CC(C)=CC(C)=C1N
MDL No. :	MFCD00972722
InChI Key :	DMEPVFSJYHJGCD-UHFFFAOYSA-N
Pubchem ID :	3613321

Safety of [ 3171-46-8 ]

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

Computational Chemistry of [ 3171-46-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	2.0
Molar Refractivity	45.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.04 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.49
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	1.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.48
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.	1.48
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	1.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.94
Solubility	1.56 mg/ml ; 0.0115 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.	-1.98
Solubility	1.42 mg/ml ; 0.0104 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	-2.42
Solubility	0.514 mg/ml ; 0.00378 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	Yes
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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.21 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	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)	1.0

Application In Synthesis of [ 3171-46-8 ]

* 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 [ 3171-46-8 ]

[ 3171-46-8 ] Synthesis Path-Downstream 1~54

1
[ 1635-84-3 ]
[ 3171-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol; for 6.0h;	To a solution of 4,6-dimethyl-2-nitroaniline (312 mg) in 5 mL MeOH, was added 10% Pd/C (50 mg). The mixture evacuated and flushed with H2 (3×), then was stirred under an atmosphere of H2 for 6 h. Conc. HCl (2 drops) was added and the mixture was stirred under H2 for an additional 18 h, then was filtered and concentrated to afford 280 mg of Intermediate 179.1, which was used without further purification.
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 3.0h;	A mixture of 4,6-dimethyl-2-nitroaniline (10.0 g, 60.2 mmol) and 10% Pd/C (1.0 g) in EtOH (300 niL) was stirred under an atmosphere of hydrogen (ca. 1 atm) for 3 h, then filtered through a Celite pad and concentrated in vacuo. The crude solid was dissolved in CH3CN (200 mL) and triphosgene (15.0 g, 50.5 mmol) was added. The mixture was stirred for 1 h, then H2O (200 mL) was added slowly and stirring was continued for 1 h. The precipitate was isolated by filtration and dried to give the title compound. MS: mlz = 163 (M + 1).

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3248 - 3255.
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 8743 - 8749.
[3]Chemische Berichte,1902,vol. 35,p. 632.
[4]Chemische Berichte,1902,vol. 35,p. 632.
[5]Journal of the American Chemical Society,1951,vol. 73,p. 5687,5690.
[6]Chemische Berichte,1976,vol. 109,p. 2243 - 2258.
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.
[8]Patent: US2006/211720,2006,A1 .Location in patent: Page/Page column 83.
[9]Patent: WO2006/31610,2006,A2 .Location in patent: Page/Page column 59.

2
[ 90111-03-8 ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1888,vol. 21,p. 2815.

3
[ 6417-44-3 ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 2677,2681.

4
[ 84-11-7 ]
[ 3171-46-8 ]
[ 104352-47-8 ]

References: [1]Chemische Berichte,1902,vol. 35,p. 641.

5
[ 75-44-5 ]
[ 3171-46-8 ]
[ 102308-68-9 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662.

6
[ 64-18-6 ]
[ 3171-46-8 ]
[ 69557-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 150℃; for 0.08333330000000001h;microwave irradiation;	Intermediate 179.1 (275 mg) in 3 mL formic acid was irradiated in a microwave reactor at 150 C. for 5 min. The mixture was diluted with water, neutralized with sat. NaHCO3, then extracted with EtOAc (3×). The organic phase was washed with water and brine, dried (Na2SO4) and concentrated to afford 245 mg of Intermediate 179.2 as an orange solid.

References: [1]Chemische Berichte,1901,vol. 34,p. 4204.
[2]Patent: US2006/211720,2006,A1 .Location in patent: Page/Page column 83.

7
[ 3171-46-8 ]
[ 108129-81-3 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 610.

8
[ 3171-46-8 ]
[ 49636-63-7 ]

References: [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6902 - 6907.
[2]Journal of the Chemical Society,1942,p. 420.

9
[ 603-35-0 ]
[ 3171-46-8 ]
[ 60190-73-0 ]

References: [1]Chemische Berichte,1976,vol. 109,p. 2243 - 2258.

10
[ 603-35-0 ]
[ 3171-46-8 ]
[ 60190-75-2 ]

References: [1]Chemische Berichte,1976,vol. 109,p. 2243 - 2258.

11
[ 824-72-6 ]
[ 3171-46-8 ]
[ 4602-06-6 ]

References: [1]Canadian Journal of Chemistry,1965,vol. 43,p. 3377 - 3386.

12
[ 6374-26-1 ]
[ 3171-46-8 ]
C₁₈H₃₂N₄O₆P₂S₂ [ No CAS ]

References: [1]Patent: US4137310,1979,A .

13
[ 3171-46-8 ]
[ 3497-00-5 ]
[ 4600-23-1 ]

References: [1]Canadian Journal of Chemistry,1965,vol. 43,p. 3377 - 3386.

14
[ 3171-46-8 ]
[ 1557-63-7 ]

References: [1]Tetrahedron Letters,1965,p. 1433 - 1436.

15
[ 99-91-2 ]
[ 3171-46-8 ]
[ 111337-08-7 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 311 - 315.
Khimiya Geterotsiklicheskikh Soedinenii,1987,vol. 23,p. 370 - 375.

16
[ 98-86-2 ]
[ 3171-46-8 ]
[ 111337-06-5 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 311 - 315.
Khimiya Geterotsiklicheskikh Soedinenii,1987,vol. 23,p. 370 - 375.

17
[ 100-19-6 ]
[ 3171-46-8 ]
[ 111337-09-8 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 311 - 315.
Khimiya Geterotsiklicheskikh Soedinenii,1987,vol. 23,p. 370 - 375.

18
[ 1676-63-7 ]
[ 3171-46-8 ]
[ 111337-07-6 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 311 - 315.
Khimiya Geterotsiklicheskikh Soedinenii,1987,vol. 23,p. 370 - 375.

19
[ 75-15-0 ]
[ 3171-46-8 ]
[ 73590-92-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

20
[ 144-62-7 ]
[ 3171-46-8 ]
5,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3248 - 3255.

22
[ 7647-01-0 ]
[ 7782-50-5 ]
[ 64-19-7 ]
[ 3171-46-8 ]
3,3,5,6-tetrachloro-4,6-dimethyl-cyclohex-4-ene-1,2-dione [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1897,vol. 296,p. 206.

24
[ 7647-01-0 ]
[ 90111-03-8 ]
tin [ No CAS ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1888,vol. 21,p. 2815.

25
[ 7647-01-0 ]
[ 6417-44-3 ]
tin [ No CAS ]
[ 95-68-1 ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 2677,2681.

26
[ 89209-03-0 ]
[ 3171-46-8 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 2277 - 2279.

27
[ 848847-23-4 ]
[ 3171-46-8 ]
2-{2-chloro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-4,6-dimethyl-1H-benzoimidazole [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6043 - 6048.

28
[ 919088-55-4 ]
[ 3171-46-8 ]
2-{2-chloro-4-[3-(4-methyl-[1,4]diazepan-1-yl)-propoxy]-phenyl}-4,6-dimethyl-1H-benzoimidazole [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6043 - 6048.

29
[ 24786-18-3 ]
[ 3171-46-8 ]
N-(5,7-dimethyl-1H-benzimidazol-2-yl)benzamide [ No CAS ]

References: [1]Heterocycles,2006,vol. 70,p. 571 - 580.

30
[ 934246-26-1 ]
[ 3171-46-8 ]
N-(5,7-dimethyl-1H-benzimidazol-2-yl)isobutyramide [ No CAS ]

References: [1]Heterocycles,2006,vol. 70,p. 571 - 580.

31
[ 3171-46-8 ]
[ 117877-36-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

32
[ 3171-46-8 ]
[ 108482-81-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

33
[ 3171-46-8 ]
[ 131859-96-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

34
[ 3171-46-8 ]
[ 131859-99-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

35
[ 3171-46-8 ]
[ 131859-95-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

36
[ 3171-46-8 ]
[ 131859-98-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

37
[ 3171-46-8 ]
[ 131860-01-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

38
[ 3171-46-8 ]
[ 131859-94-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

39
[ 3171-46-8 ]
[ 131860-00-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 989 - 991.

40
[ 2050-43-3 ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1876,vol. 9,p. 1296.

41
[ 90434-19-8 ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1888,vol. 21,p. 2815.

42
[ 108-38-3 ]
[ 3171-46-8 ]

References: [1]Chemische Berichte,1888,vol. 21,p. 2815.

43
[ 3171-46-8 ]
[ 115003-10-6 ]

References: [1]Journal of Organic Chemistry,1958,vol. 23,p. 610.

44
[ 3171-46-8 ]
[ 102457-53-4 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662.

45
[ 3171-46-8 ]
1,3,4,6-tetramethyl-2,3-dihydro-1H-benzimidazol-2-ol [ No CAS ]

References: [1]Chemische Berichte,1901,vol. 34,p. 4204.

46
[ 3171-46-8 ]
3,5,N,N'-tetramethyl-o-phenylenediamine [ No CAS ]

References: [1]Chemische Berichte,1901,vol. 34,p. 4204.

47
[ 3171-46-8 ]
1,3,4,6-tetramethyl-benzimidazolium; iodide [ No CAS ]

References: [1]Chemische Berichte,1901,vol. 34,p. 4204.

48
[ 848849-19-4 ]
[ 3171-46-8 ]
4,6-Dimethyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; In DMF (N,N-dimethyl-formamide); at 90℃; for 18.0h;	To a stirred solution of 2-[4-(1-methyl-piperidin-4-yl)-butoxy]-isonicotinonitrile (440 mg, 1.61 mmol, 1.0 equiv) in toluene (5.0 mL) at 0 C. was added 1.0 M diisobutylaluminum hydride in toluene (2.41 mL, 2.41 mmol, 1.5 equiv). After 3 h, methanol (8 mL) and 1.0 M H2SO4 (5 mL) were added. The mixture was stirred for 30 min, and then 1.0 M NaOH (10 mL) was added, followed by satd. aq. sodium potassium tartrate (40 mL) and dichloromethane (100 mL). After stirring for 30 min, the mixture was extracted with chloroform (3×50 mL) and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was partially purified by Method 2 to afford 318 mg of a mixture of 2-(4-piperidin-4-yl-butoxy)-pyridine-4-carbaldehyde and several other unidentified products. A portion of the crude of 2-(4-piperidin-4-yl-butoxy)-pyridine-4-carbaldehyde (100 mg), <strong>[3171-46-8]3,5-dimethyl-benzene-1,2-diamine</strong> (70 mg), and Na2S2O5 (93 mg) were stirred in DMF (3 mL) at 90 C. for 18 h. The reaction mixture was loaded directly on silica gel and purified according to Method 2, which afforded 38 mg of the title compound. MS (electrospray): mass calculated for C24H32N4O, 392.26; m/z found 393.4 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.25 (d, J=5.3 Hz, 1H), 7.62 (dd, J=4.5, 1.0 Hz, 1H), 7.48 (s, 1H), 7.24 (s, 1H), 6.95 (s, 1H), 4.34 (t, J=6.6 Hz, 2H), 2.91-2.83 (m, 2H), 2.58 (s, 3H), 2.43 (s, 3H), 2.25 (s, 3H), 2.07-1.95 (m, 2H), 1.86-1.69 (m, 5H), 1.57-1.18 (m, 6H).

References: [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 52-53.

49
C₁₅H₂₃N₃O₂ [ No CAS ]
[ 3171-46-8 ]
4,6-Dimethyl-2-{2-[4-(4-methyl-piperazin-1-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; In DMF (N,N-dimethyl-formamide); at 90℃; for 18.0h;	To a stirred solution of 2-[4-(4-methyl-piperazin-1-yl)-butoxy]-isonicotinonitrile) in toluene (5.0 mL) at 0 C. was added 1.5 M diisobutylaluminum hydride in toluene (3.9 mL, 5.86 mmol, 1.5 equiv). After 3 h, methanol (9 mL) and 1.0 M H2SO4 (10 mL) were added. The mixture was stirred for 30 min, and then 1.0 M NaOH (10 mL) was added, followed by satd. aq. sodium potassium tartrate (40 mL) and dichloromethane (100 mL). After stirring for 30 min, the mixture was extracted with chloroform (3×50 mL) and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was partially purified by Method 2 to afford 240 mg of a mixture of 3-[3-(1-methyl-piperidin-4-yloxy)-propoxy]-benzaldehyde and several other unidentified products. A portion of the the crude 3-[3-(1-methyl-piperidin-4-yloxy)-propoxy]-benzaldehyde (40 mg), <strong>[3171-46-8]3,5-dimethyl-benzene-1,2-diamine</strong> (17.6 mg), and Na2S2O5 (32 mg) were stirred in DMF (4 mL) at 90 C. for 18 h. The reaction mixture was loaded directly on silica gel and purified by Method 2, which afforded 19 mg of the title compound. MS (electrospray): mass calculated for C23H31N5O, 393.25; m/z found, 394.5 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.26 (d, J=5.4 Hz, 1H), 7.63 (d, J=5.5 Hz, 1H), 7.49 (s, 1H), 7.25 (br s, 1H), 6.95 (s, 1H), 4.38 (t, J=6.3 Hz, 2H), 2.76-2.33 (m, 16H), 2.32-2.24 (s, 3H), 1.92-1.79 (m, 2H), 1.79-1.66 (m, 2H).

References: [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 50.

50
C₁₇H₂₆N₂O₂ [ No CAS ]
[ 3171-46-8 ]
4,6-Dimethyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; In DMF (N,N-dimethyl-formamide); at 90℃; for 18.0h;	To a stirred solution of impure 3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-isonicotinonitrile (283 mg) at 0 C. was added 1.5 M diisobutylaluminum hydride in toluene (1.32 mL). After 3 h, methanol (8 mL) and 1.0 M H2SO4 (5 mL) were added. The mixture was stirred for 30 min, then 1.0 M NaOH (10 mL) was added, followed by satd. aq. sodium potassium tartrate (40 mL) and dichloromethane (100 mL). After stirring for 30 min, the mixture was extracted with chloroform (3×50 mL) and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was partially purified by Method 2 to afford 180 mg of a mixture of 2-(4-piperidin-4-yl-butoxy)-pyridine-4-carbaldehyde and several other unidentified products. A portion of the impure 2-(4-piperidin-4-yl-butoxy)-pyridine-4-carbaldehyde (19.5 mg), <strong>[3171-46-8]3,5-dimethyl-benzene-1,2-diamine</strong> (9.2 mg), and Na2S2O5 (16.6 mg) were stirred in DMF (3 mL) at 90 C. for 18 h. The reaction mixture was loaded directly on silica gel and purified by Method 2, which afforded 9.4 mg of the title compound. MS (electrospray): mass calculated for C25H34N4O, 406.27; m/z found, 407.5 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.06 (dd, J=5.3, 0.4 Hz, 1H), 7.23 (s, 1H), 7.13 (d, J=5.3 Hz, 1H), 6.94 (s, 1H), 4.36 (t, J=6.4 Hz, 2H), 2.92-2.81 (m, 2H), 2.56 (s, 3H), 2.43 (s, 3H), 2.33 (s, 3H), 2.24 (s, 3H), 2.07-1.94 (m, 2H), 1.87-1.67 (m, 4H), 1.60-1.46 (m, 2H), 1.40-1.15 (m, 5H).

References: [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 54-55.

51
[ 848849-58-1 ]
[ 3171-46-8 ]
{4-(4,6-Dimethyl-1H-benzoimidazol-2-yl)-6-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-3-yl}-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; In DMF (N,N-dimethyl-formamide); at 90℃; for 36.0h;	5-Bromo-4-dimethoxymethyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridine (0.5 g, 1.25 mmol, 1.0 equiv) was dissolved in THF (6 mL) and cooled to -78 C. A 2.5 M solution of n-butyllithium in hexanes (0.6 mL, 1.5 mmol, 1.2 equiv) was added dropwise. The solution was stirred for 45 min, and then DMF (0.55 mL, 1.25 mmol, 1.0 equiv) was added. After 1 h, sodium borohydride (38 mg, 1.36 mmol, 1.1 equiv) was added. The mixture was allowed to warm to -40 C. for 30 min, then was quenched with satd. aq. NaHCO3 (10 mL). The mixture was extracted with chloroform (3×30 mL), and the combined extracts were dried (Na2SO4), filtered, and concentrated to afford {4-dimethoxymethyl-6-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-3-yl}-methanol as a crude mixture. This crude material (88 mg) was dissolved in THF (3 mL) and 1.0 M HCl (3 mL) was added portionwise over 3 h at 60 C. The mixture was cooled, satd. aq. NaHCO3 was added, and the mixture was extracted with chloroform (3×30 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated. A portion of the resulting crude 5-hydroxymethyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridine-4-carbaldehyde (33 mg), <strong>[3171-46-8]3,5-dimethyl-benzene-1,2-diamine</strong> (22 mg), and Na2S2O5 (36 mg) were stirred in DMF (2 mL) at 90 C. for 36 h. The reaction mixture was purified by Method 2 to afford 5.3 mg of the title compound. MS (electrospray): mass calculated for C25H34N4O2, 422.27; m/z found, 423.5 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.21 (s, 1H), 7.30 (s, 1H), 7.23 (br s, 1H), 6.95 (br s, 1H), 4.68 (s, 2H), 4.34 (t, J=6.4 Hz, 2H), 2.95-2.82 (m, 2H), 2.57 (s, 3H), 2.44 (s, 3H), 2.27 (s, 3H), 2.11-1.98 (m, 2H), 1.86-1.68 (m, 4H), 1.57-1.44 (m, 2H), 1.39-1.15 (m, 5H).

References: [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 60.

52
[ 3171-46-8 ]
[ 89209-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-phenylsulfinylamine; In toluene; for 20.0h;Heating / reflux;	A solution of 3, 5-dimethyl-benzene-1, 2-diamine (87.5 g) and N-THIONYLANILINE (365 g) in abs. toluene (900 ml) is REFLUXED for 20 hours. The reaction mixture is cooled, then stirred for 10 min. with 6N hydrochloric acid (900 ML). The layers are separated and the organic layer is evaporated. The remaining oil is destilled in high vacuum to give 4, 6-dimethyl-benzo [1,2, 5] thiadiazole. Bp = 80 , 0.1 Torr.

References: [1]Patent: WO2004/69257,2004,A1 .Location in patent: Page/Page column 6.

53
[ 32315-10-9 ]
[ 3171-46-8 ]
[ 102308-68-9 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 1.0h;	A mixture of 4,6-dimethyl-2-nitroaniline (10.0 g, 60.2 mmol) and 10% Pd/C (1.0 g) in EtOH (300 niL) was stirred under an atmosphere of hydrogen (ca. 1 atm) for 3 h, then filtered through a Celite pad and concentrated in vacuo. The crude solid was dissolved in CH3CN (200 mL) and triphosgene (15.0 g, 50.5 mmol) was added. The mixture was stirred for 1 h, then H2O (200 mL) was added slowly and stirring was continued for 1 h. The precipitate was isolated by filtration and dried to give the title compound. MS: mlz = 163 (M + 1).

References: [1]Patent: WO2006/31610,2006,A2 .Location in patent: Page/Page column 59.

54
[ 1635-84-3 ]
[ 3171-45-7 ]
[ 3171-46-8 ]

Yield	Reaction Conditions	Operation in experiment
1.300 g (96%)	palladium-carbon; In ethanol;	1,2-Diamino-4,6-dimethylbenzene. A mixture of 4,6-dimethyl-2-nitroaniline (1.66 g, 10.0 mmole) and 10% Pd/C (200 mg) in ethanol (35 mL) was hydrogenated for 2 h at room temperature under 25 psi H2. The catalyst was removed by filtration with celite and the solvent was removed by rota-evaporation to give 1.300 g (96%) of 1,2-diamino-4,5-dimethylbenzene as a brown solid. 1 H NMR (CDCl3): 6.449 (s, 1H), 6.469 (s, 1H), 3.327 (br, 2H), 3.259 (br, 2H), 2.190 (s, 3H), 2.159 (s, 3H).

References: [1]Patent: US5631373,1997,A .

Historical Records

Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Friedel-Crafts Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 3171-46-8 ]

Aryls

A358547 [2687-25-4]

3-Methylbenzene-1,2-diamine

Similarity: 0.96

A157266 [136583-84-1]

4-Ethylbenzene-1,2-diamine dihydrochloride

Similarity: 0.87

A838163 [1639-31-2]

3,4,5-Trimethylaniline

Similarity: 0.86

A305051 [131019-87-9]

N1,5-Dimethylbenzene-1,2-diamine

Similarity: 0.82

A238320 [32202-61-2]

2,3-Dihydro-1H-inden-4-amine

Similarity: 0.81

Amines

A358547 [2687-25-4]

3-Methylbenzene-1,2-diamine

Similarity: 0.96

A157266 [136583-84-1]

4-Ethylbenzene-1,2-diamine dihydrochloride

Similarity: 0.87

A838163 [1639-31-2]

3,4,5-Trimethylaniline

Similarity: 0.86

A305051 [131019-87-9]

N1,5-Dimethylbenzene-1,2-diamine

Similarity: 0.82

A238320 [32202-61-2]

2,3-Dihydro-1H-inden-4-amine

Similarity: 0.81

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CAS No.: 3171-46-8

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CAS No.: 3171-46-8

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Lipophilicity

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[ 3171-46-8 ] Synthesis Path-Downstream 1~54

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