6971-45-5|2-Methoxyphenylhydrazine Hydrochloride| Ambeed

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Quality Control of [ 6971-45-5 ] Purity: 96% SDS Specification

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Product Details of [ 6971-45-5 ]

CAS No. :	6971-45-5
Formula :	C₇H₁₁ClN₂O
M.W :	174.63
SMILES Code :	NNC1=CC=CC=C1OC.[H]Cl
MDL No. :	MFCD00035456
InChI Key :	HECSHXUNOVTAIJ-UHFFFAOYSA-N
Pubchem ID :	2849445

Safety of [ 6971-45-5 ]

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

Computational Chemistry of [ 6971-45-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	45.99
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	47.28 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	-3.89
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	2.24
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.	1.41
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	0.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.31

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.6
Solubility	0.437 mg/ml ; 0.00252 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.	-2.87
Solubility	0.235 mg/ml ; 0.00135 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < 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	-2.19
Solubility	1.13 mg/ml ; 0.00649 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	Yes
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.	-5.77 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)	1.45

Application In Synthesis of [ 6971-45-5 ]

* 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 [ 6971-45-5 ]

[ 6971-45-5 ] Synthesis Path-Downstream 1~35

1
[ 6971-45-5 ]
[ 49752-93-4 ]
[ 68528-93-8 ]

References: [1]Pharmazie,1978,vol. 33,p. 575 - 577.

2
[ 2555-37-5 ]
[ 6971-45-5 ]
[ 110570-16-6 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1 - 3.

3
[ 64-17-5 ]
[ 56611-61-1 ]
[ 6971-45-5 ]
[ 94569-01-4 ]

References: [1]European Journal of Medicinal Chemistry,1984,vol. 19,p. 223 - 228.

4
[ 38768-08-0 ]
[ 6971-45-5 ]
[ 53526-99-1 ]
6,6'-bis<(2-methoxyphenyl)hydrazono>-1,1'-bi(2,4-cycloheptadiene)-7,7'-dione [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 2531 - 2540.

5
[ 56611-61-1 ]
[ 6971-45-5 ]
3-(2-Methoxy-phenyl)-5,7-dimethyl-4-oxo-1,2,3,4-tetrahydro-phthalazine-6-carboxylic acid ethyl ester [ No CAS ]
3-(2-Methoxy-phenyl)-5,7-dimethyl-4-oxo-1,2,3,4-tetrahydro-phthalazine-1,6-dicarboxylic acid 6-ethyl ester [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1984,vol. 19,p. 223 - 228.

6
[ 109248-35-3 ]
[ 6971-45-5 ]
[ 121953-66-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 2531 - 2540.

7
[ 80030-73-5 ]
[ 6971-45-5 ]
[ 81016-49-1 ]

References: [1]Synthesis,1982,p. 70 - 71.
[2]Arzneimittel-Forschung/Drug Research,1999,vol. 49,p. 997 - 1000.

8
[ 16676-29-2 ]
[ 6971-45-5 ]
[ 126642-52-2 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1714 - 1720.

9
[ 6971-45-5 ]
[ 118818-06-7 ]
4-(1-acetamidoethyl)-2-<2-(2-methoxyphenyl)hydrazino>tropone [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 2531 - 2540.

10
[ 6971-45-5 ]
[ 118818-07-8 ]
4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-2-<2-(2-methoxyphenyl)hydrazino>tropone [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 2531 - 2540.

11
[ 6971-45-5 ]
[ 52649-04-4 ]
[ 87650-47-3 ]

References: [1]Chemistry of Heterocyclic Compounds,1983,vol. 19,p. 863 - 867.
Khimiya Geterotsiklicheskikh Soedinenii,1983,vol. 19,p. 1076 - 1081.

12
[ 6971-45-5 ]
[ 1467-79-4 ]
C₁₀H₁₆N₄O [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 185 - 193.

13
[ 6971-45-5 ]
6aα-(2-methoxyethyl)-9-oxo-9aαH,9bαH-perhydropyrrolo<3,2,1-ij>quinoline [ No CAS ]
N-[(6aS,9aS,9bR)-6a-(2-Methoxy-ethyl)-decahydro-pyrrolo[3,2,1-ij]quinolin-(9E)-ylidene]-N'-(2-methoxy-phenyl)-hydrazine [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 2467 - 2476.

14
[ 6971-45-5 ]
[ 157752-16-4 ]
(-)-(2S,6R)-3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-10-methoxy-6H-azocino[4,5-b]indol-6-yl)phenol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2081 - 2086.

15
[ 6971-45-5 ]
(1S,5S)-5-(3-Hydroxy-phenyl)-2-methyl-2-aza-bicyclo[3.3.1]nonan-7-one; hydrobromide [ No CAS ]
3-(1,2,3,4,5,11-hexahydro-3-methyl-2,6-methano-10-methoxy-6H-azocino[4,5-b]indol-6-yl)phenol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2081 - 2086.

16
[ 6971-45-5 ]
[ 95-92-1 ]
[ 121-97-1 ]
[ 501426-51-3 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 642 - 645.

17
[ 4724-62-3 ]
[ 6971-45-5 ]
[ 503000-58-6 ]

References: [1]Organic Letters,2003,vol. 5,p. 749 - 751.

18
[ 6971-45-5 ]
[ 29976-53-2 ]
[ 688028-95-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 717 - 722.

19
[ 6971-45-5 ]
[ 82874-96-2 ]
[ 1026587-55-2 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5298 - 5315.

20
[ 1118-61-2 ]
[ 6971-45-5 ]
[ 91331-85-0 ]

Yield	Reaction Conditions	Operation in experiment
95%		2.000 g (11.453 mmol) of <strong>[6971-45-5]2-methoxyphenylhydrazine hydrochloride</strong> was put in 10 ml of IN hydrochloric acid and 0.997 g (12.140 mmol) of 3-aminocrotonic nitrile was added. The mixture was stirred for 18 h at 1000C. After cooling, the pH value of the mixture was adjusted with IN sodium hydroxide solution to pH > 12. It was extracted with dichloromethane three times. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The product was dried under high vacuum. We obtained 2.430 g (purity according to LC-MS 91%, 95% of theor.) of the target compound.LC-MS (method 3): R, = 0.31 min; MS (EIpos): m/z = 204 [M+H]+.
86%		IM07: 2-(2-Methoxy-phenyl)-5-methyl-2H-pyrazol-3-ylamineTo a solution of (2-methoxy-phenyl)-hydrazine HCl salt (10.0 g, 57.3 mmol) in concentrated aqueous HCl (50 mL) was added 3-amino-but-2-enenitrile (5.0 g, 60.9 mmol) at room temperature. The reaction temperature was increased to 100 C. and the mixture was stirred at this temperature for 18 h. The reaction mixture was cooled to room temperature and then poured into ice-cold 2N NaOH solution (200 mL). The resulting mixture was filtered. The remanens was washed with water (200 mL) and dried in vacuo to give the title compound as an off-white solid (10.0 g, 86%). 1H NMR (DMSO-d6, 400 MHz) delta 7.39-7.35 (1H, m), 7.24-7.22 (1H, m), 7.17-7.15 (1H, m), 7.03-6.99 (1H, m), 5.21 (1H, s), 4.76 (2H, s), 3.78 (3H, s), 2.02 (3H, s).
86%	With hydrogenchloride; at 20 - 100℃; for 18h;	General procedure: To a solution of (2-methoxy-phenyl)-hydrazine HCI salt (10.0 g, 57.3 mmol) in concentrated aqueous HCI (50 mL) was added 3-amino-but-2-enenitrile (5.0 g, 60.9 mmol) at room tem- perature. The reaction temperature was increased to 100 C and the mixture was stirred at this temperature for 18 h. The reaction mixture was cooled to room temperature and then poured into ice-cold 2N NaOH solution (200 mL). The resulting mixture was filtered. The re- manens was washed with water (200 mL) and dried in vacuo to give the title compound as an off-white solid (10.0 g, 86 %). 1 H NMR (DMSO-d6, 400 MHz) delta 7.39-7.35 (1 H, m), 7.24-7.22 (1 H, m), 7.17-7.15 (1 H, m), 7.03-6.99 (1 H, m), 5.21 (1 H, s), 4.76 (2H, s), 3.78 (3H, s), 2.02 (3H, s).

References: [1]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 89.
[2]Patent: US2013/5743,2013,A1 .Location in patent: Page/Page column 13.
[3]Patent: WO2013/4617,2013,A1 .Location in patent: Page/Page column 31.
[4]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 1098 - 1104.

21
[ 6971-45-5 ]
[ 6946-05-0 ]
1,10-dimethoxy-11,12-dihydro-11,12-diaza-indeno[2,1-a]fluorene [ No CAS ]

References: [1]Synlett,2005,p. 42 - 48.

22
[ 6971-45-5 ]
[ 17823-69-7 ]
5-amino-4-carboxamido-1-(2-methoxyphenyl)-3-(methylthio)pyrazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5894 - 5911.

23
[ 6971-45-5 ]
[ 21243-15-2 ]
[ 880552-73-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237.

24
[ 86996-25-0 ]
[ 6971-45-5 ]
[ 918792-66-2 ]

Yield	Reaction Conditions	Operation in experiment
4%	With acetyl chloride; In ethanol; for 57h;Heating / reflux;	Preparation 7N-(8-methoxy-2,3,4,9-tetrahydro-lH-carbazol-3-yl)-isobutyramideAdd acetyl chloride (34.1 mL, 480 mmol) portionwise to absolute ethanol (120 mL) cooled in an ice bath and stir for 2 h. Add 4-methoxyphenylhydrazine hydrochloride (1.74 g, 10 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (Preparation 2) (1.83 g, 120 mmol) and reflux with stirring for 18 h. Follow the procedures essentially as described in Preparation 6, above, to give 6.0 g green gum after workup. Pass over a silica pad eluting with dichloromethane/25% ethyl acetate to provide 1.29 g of a brown foam. Further purify the residue by flash EPO <DP n="90"/>chromatography, eluting with dichloromethane, dichloromethane/25% ethyl acetate and then a gradient up to dichloromethane/40% ethyl acetate to obtain a pale tan solid. Triturate in diethyl ether with a bit of hexane to give 421 mg (4%) of an off- white solid. MS (ES): m/z 287 (M+l), 285 (M-I); 1H NMR(DMS0-d6): delta 10.77 (s, IH), 7.83 (d, IH, J = 7.5 Hz), 6.95 (d, IH, J = 7.9 Hz), 6.86 (t, IH, J = 7.7 Hz), 6.61 (d, IH, J = 7.5 Hz), 4.02 (m, IH), 3.90 (s, 3H), 2.89 (dd, IH, J = 15.0, 5.3 Hz), 2.76 (m, 2H), 2.50-2.34 (m, 3H), 1.95 (m, IH), 1.76 (m, IH), 1.03 (d, 6H, / = 7.0 Hz).

References: [1]Patent: WO2007/2181,2007,A2 .Location in patent: Page/Page column 88-89.

25
C₂₂H₂₁FN₄O₄S [ No CAS ]
[ 6971-45-5 ]
C₂₇H₂₃FN₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 85℃; for 7.25h;	After adding 140 mg of potassium carbonate and 140 mg of iodomethane to a 3 ml DMF solution containing 220 mg of {2-(2-fluoro-3-hydroxy-5-methylphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester, the mixture was stirred at room temperature for 17 hours and 15 minutes. Ethyl acetate and water were added to the reaction mixture, and extraction was performed twice with ethyl acetate. The combined organic layers were washed twice with water and dried using magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. Half of the obtained residue was dissolved in 1 ml of DMF, and after adding 38 mg of <strong>[6971-45-5](2-methoxyphenyl)hydrazine hydrochloride</strong> and 0.070 ml of triethylamine to the solution, the mixture was stirred at 85 C. for 7 hours and 15 minutes under a nitrogen atmosphere. The reaction mixture was then concentrated. Next, 1 ml of methanol and 0.090 ml of acetic acid were added to dissolve the obtained residue. To this solution there was added 100 mg of sodium cyanotrihydroborate, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was then concentrated. Next, 3 ml of a methanol:water:acetic acid=1:1:1 mixed solvent was added to dissolve the obtained residue. After adding 140 mg of iron powder to the solution, the mixture was stirred at 55 C. for 17 hours and 15 minutes under a nitrogen atmosphere. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid) to give the title compound (4.15 mg) as a white solid. 1H-NMR (CD3OD) delta 2.31 (s, 3H) 3.82 (s, 3H) 3.87 (s, 3H) 5.95 (s, 1H) 6.83-6.86 (m, 3H) 6.94 (dd, J=2.0, 8.0 Hz, 1H) 7.02 (dt, J=0.8, 8.0 Hz, 1H) 7.14 (dd, J=1.2, 8.4 Hz, 1H) 7.30 (dd, J=1.6, 7.6 Hz, 1H) 7.43 (ddd, J=1.2, 7.2, 8.4 Hz, 1H) 7.62-7.65 (m, 2H) Mass spectrum (ESI) m/z: 477 (M+H)+

References: [1]Patent: US2008/15199,2008,A1 .Location in patent: Page/Page column 51-52.

26
[ 6971-45-5 ]
3-fluoro-11-methyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-10-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237.

27
[ 6971-45-5 ]
[ 880552-88-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237.

28
[ 6971-45-5 ]
1-(2-methoxy-phenyl)-6-methyl-3-methylsulfanyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5894 - 5911.

29
[ 6971-45-5 ]
[ 1027404-18-7 ]