5978-75-6|9H-Fluoren-9-amine hydrochloride| Ambeed

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Quality Control of [ 5978-75-6 ] Purity: 95% SDS Specification

COA

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NMR

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Product Details of [ 5978-75-6 ]

CAS No. :	5978-75-6
Formula :	C₁₃H₁₂ClN
M.W :	217.69
SMILES Code :	NC1C2=C(C3=C1C=CC=C3)C=CC=C2.[H]Cl
MDL No. :	MFCD00012536
InChI Key :	SYKJOJSYQSVNOM-UHFFFAOYSA-N
Pubchem ID :	2724685

Safety of [ 5978-75-6 ]

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

Computational Chemistry of [ 5978-75-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	12
Fraction Csp3	0.08
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	64.56
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	2.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.19
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.	2.95
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	2.85
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.66
Solubility	0.0477 mg/ml ; 0.000219 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.	-3.19
Solubility	0.141 mg/ml ; 0.000646 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	-4.6
Solubility	0.00552 mg/ml ; 0.0000254 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.51 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)	2.49

Application In Synthesis of [ 5978-75-6 ]

* 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.

Downstream synthetic route of [ 5978-75-6 ]

[ 5978-75-6 ] Synthesis Path-Downstream 1~35

1
[ 358-23-6 ]
[ 5978-75-6 ]
[ 58044-90-9 ]

References: [1]Tetrahedron,1975,vol. 31,p. 2517 - 2521.

2
[ 20615-64-9 ]
[ 5978-75-6 ]
[ 16504-38-4 ]

References: [1]Journal of Organic Chemistry,1968,vol. 33,p. 2411 - 2416.

3
[ 5978-75-6 ]
[ 107-14-2 ]
2-Chloro-N-(9H-fluoren-9-yl)-acetamidine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1979,vol. 22,p. 295 - 301.

4
[ 455-19-6 ]
[ 5978-75-6 ]
[ 123500-15-2 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

5
[ 1684-29-3 ]
[ 5978-75-6 ]
N-(9-Fluorenyl)-2,5-anhydro-2,5-imino-D-glucitol [ No CAS ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 3175 - 3185.

6
[ 5978-75-6 ]
[ 100-52-7 ]
[ 81532-35-6 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

7
[ 5978-75-6 ]
[ 123-11-5 ]
[ 118133-90-7 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

8
[ 5978-75-6 ]
[ 123-11-5 ]
[ 118133-90-7 ]

References: [1]Tetrahedron,1987,vol. 43,p. 5887 - 5898.

9
[ 5978-75-6 ]
[ 1122-91-4 ]
[ 123500-14-1 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

10
[ 5978-75-6 ]
[ 100-10-7 ]
[ 123500-13-0 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

11
[ 5978-75-6 ]
[ 160560-23-6 ]
(+/-)-2-cyano-3,3-diphenyl-N-(9-fluorenyl)propionamide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 155 - 160.

12
[ 5978-75-6 ]
[ 486-25-9 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 5192 - 5201.

13
[ 358-23-6 ]
[ 5978-75-6 ]
[ 749874-56-4 ]
2',5'-diphenylspiro[9H-flourene-9,4'-(4H)imidazole] [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 2567 - 2581.

14
[ 358-23-6 ]
[ 5978-75-6 ]
[ 749874-57-5 ]
2',5'-bis(4-methylphenyl)spiro[9H-flourene-9,4'-(4H)imidazole] [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 2567 - 2581.

15
[ 358-23-6 ]
[ 5978-75-6 ]
[ 749874-58-6 ]
2',5'-bis(4-methoxyphenyl)spiro[9H-flourene-9,4'-(4H)imidazole] [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 2567 - 2581.

16
[ 5978-75-6 ]
[ 123500-30-1 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

17
[ 5978-75-6 ]
[ 123500-29-8 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

18
[ 5978-75-6 ]
[ 123500-31-2 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.

19
[ 5978-75-6 ]
[ 118133-84-9 ]

References: [1]Tetrahedron,1989,vol. 45,p. 1723 - 1746.
[2]Tetrahedron,1987,vol. 43,p. 5887 - 5898.

20
N-[4-formyl-2-(2-methylphenyl)benzoyl]methionine methyl ester [ No CAS ]
[ 5978-75-6 ]
N-[4-(N-(Fluoren-9-yl)aminomethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		N-[4-(N-(Fluoren-9-yl)aminomethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester The desired compound was prepared using the method described in Example 403H starting with N-[4-formyl-2-(2-methylphenyl)benzoyl]methionine methyl ester, prepared as in Example 403G, and <strong>[5978-75-6]9-aminofluorene hydrochloride</strong> salt m/e (ESI) 551 (MH+)

References: [1]Patent: US6310095,2001,B1 .

21
[ 7285-11-2 ]
[ 5978-75-6 ]
[ 2004-06-0 ]
N₆-fluorenyladenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; water;	EXAMPLE 1 N6 -Fluorenyladenosine 4.0 g of 6-chloropurine riboside, 3.79 g of <strong>[5978-75-6]9-aminofluorene hydrochloride</strong> and 3.52 g of triethylamine are refluxed in 100 ml ethanol under nitrogen for 20 hrs. the solvent is evaporated to dryness and residue is treated with 100 ml of cold water. Precipitated solid is filtered and treated with 50 ml of methanol-chloroform (1:1) affording 3.8 g (63%) of N6 -fluorenyladenosine having a m.p of 210-212 C. Anals. Calcd. for C23 H21 N5 O4. 10 H2 O 0.3HCl C=60.00; H=5.09; N=15.21. Found: C=59.95; H=4.72; N=15.13.

References: [1]Patent: US4593019,1986,A .

22
aqueous bicarbonate [ No CAS ]
[ 5978-75-6 ]
[ 144-55-8 ]
[ 151520-60-4 ]
[ 160000-39-5 ]

Yield	Reaction Conditions	Operation in experiment
325 mg (56%)	With pyridine; thionyl chloride; trifluoroacetic acid; In dichloromethane; ethyl acetate; toluene;	G. 17beta-N-9-Fluorenyl-carbamoyl-6-azaandrost-4-en-3-one A sample of 17beta-carboxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one (502 mg, 1.20 mmol), from part F, is suspended in toluene (15 mL), treated with pyridine (0.15 mL, 1.5 eq.), cooled to 0 C. and thionyl chloride added (0.13 mL, 1.5 eq.). After 1 hr at 0 C. the reaction is concentrated to a yellow solid, this crude acid chloride is dissolved in methylene chloride (15 mL) and added to a biphasic mixture of methylene chloride (5 mL) and saturated aqueous NaHCO3 (5 mL) which contains 9-fluorenyl amine hydrochloride (2.5 eq.). After stirring 45 min, ethyl acetate (50 mL) is added, the layers separated, the ethyl acetate layer washed with saturated aqueous NaHSO4, saturated aqueous NaCl, dried over MgSO4, concentrated and chromatographed on silica gel (35-50% ethyl acetate/hexanes) to give 171beta-N-9-fluorenyl-carbamoyl-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one as a yellow oil; yield: 558 mg (80%). This material is dissolved in methylene chloride (15 mL) and treated with trifluoroacetic acid (2 mL at room temperature. After 3 hrs the reaction is concentrated, methylene chloride (50 mL) and saturated aqueous bicarbonate (50 mL) added, the layers separated, methylene chloride washed with saturated aqueous NaCl, dried over MgSO4, concentrated and crystallized from acetonitrile to give 17beta-N-9-fluorenyl-carbamoyl-6-azaandrost-4-en-3-one as a white crystalline solid; yield: 325 mg (56%); m. p. 227-230 C. Anal. Calcd. for C32 H36 N2 O2.1/2H2 O; C, 78.49; H, 7.62; N, 5.72. Found: C, 78.25; H, 7.67; N, 5.65.

References: [1]Patent: US5708001,1998,A .

23
[ 901776-33-8 ]
[ 5978-75-6 ]
[ 901775-44-8 ]

Yield	Reaction Conditions	Operation in experiment
57.7%		EXAMPLE 254-(((2S,3S,4R,5R)-5-(6-(9H-fluoren-9-ylamino)-2-chloro-9H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methylthio)-2-aminobutanoic acid 24bMethod BA solution of 23 (75 mg, 0.0989 mmol), triethylamine (83 muL, 6 eq) and <strong>[5978-75-6]9-aminofluorene hydrochloride</strong> (64.6 mg, 0.3 mmol) in a mixture of 1,2-dichloroethane (0.75 ml) and ethanol (0.75 ml) was heated to 50 C.-60 C. overnight. The reaction was then cooled to room temperature and the solvent was evaporated. THF (0.5 ml) was added followed by 1.0 M KOH (1.5 ml). The solution was stirred for 3 hours and the solvent was removed to give the crude product which was purified by flash chromatography using 60% CHCl3, 30% methanol and 10% NH4OH followed by trituration with CH3CN to give the title compound 24b in 57.7% yield(25 mg). 1H NMR (DMSO-d6/D2O, 400 MHz): delta ppm: 8.38 (s, 1H), 7.84 (d, 2H, J=7.2 Hz), 7.25-7.48 (m, 4H), 7.25-7.31 (m, 2H), 6.50 (m, 1H), 5.84 (d, 1H, J=6.0 Hz), 4.65 (m, 1H), 4.10-4.16 (m, 1H), 4.05 (m, 1H), 3.22-3.37 (m, 1H), 2.77-2.96 (m, 2H), 2.62 (t, 2H, J=7.6 Hz), 1.99 (m, 1H), 1.79 (m, 1H). MS calc 582, found 583 (MH+).

References: [1]Patent: US2008/132525,2008,A1 .Location in patent: Page/Page column 22.

24
[ 958245-14-2 ]
[ 5978-75-6 ]
[ 958244-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; for 20.5h;Heating / reflux;	Triethylamine (34 muL) and diphenylphosphoryl azide (50 muL) were added to a suspension containing 4-(1H-imidazol-1-yl)-3-methoxybenzoic acid (51 mg) in THF (2 mL), and the reaction solution was heated under reflux until it was converted into a solution. The reaction solution was further heated under reflux for 30 minutes, and <strong>[5978-75-6]9-aminofluorene hydrochloride</strong> (51 mg) was added to the reaction solution with heating under reflux. The reaction solution was further heated under reflux for 20 hours. The reaction solution was returned to room temperature. Water and ethyl acetate were added and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by LC-MS and then washed with a saturated sodium bicarbonate solution to obtain the title compound (30 mg). The property values of the compound are as follows. 1H-NMR (CD3OD) delta (ppm): 3.88 (s, 3H), 6.00 (s, 1H), 6.99 (dd, J = 8.4, 2.0 Hz, 1H), 7.07 (s, 1H), 7.43-7.25 (m, 6H), 7.64-7.62 (m, 3H), 7.77 (m, 2H), 7.82 (s, 1H). ESI-MS; m/z 397 [M+ + H].

References: [1]Patent: EP2019093,2009,A1 .Location in patent: Page/Page column 46.

25
C₁₅H₁₇N₃O₃ [ No CAS ]
[ 5978-75-6 ]
[ 958227-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Synthesis of (E)-N-(9H-fluoren-9-yl)-3-[3-methoxy-4-(3-methyl-1H-[1,2,4]triazol-1-yl)phenyl]acrylamide; Triethyl phosphonoacetate (88 muL) and lithium hydroxide monohydrate (18.5 mg) were added to a solution of 3-methoxy-4-(3-methyl-1H-[1,2,4]triazol-1-yl)benzaldehyde (80.0 mg) in THF (3.0 mL), and the reaction solution was stirred at room temperature for one hour and 45 minutes. After confirming that the raw materials were eliminated, a 2 N sodium hydroxide solution (3.0 mL) was added to the reaction solution. The reaction solution was stirred at room temperature overnight and then stirred at 60C for five hours and 15 minutes. 2 N hydrochloric acid and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 125 mg of a crude cinnamic acid compound. 9-Aminofluorene monohydrochloride [CAS No.5978-75-6] (55.2 mg), IPEA (147 muL), HOBT (34.4 mg) and EDC (48.6 mg) were sequentially added to a solution of the resulting crude cinnamic acid compound (125 mg) in DMF (1.0 mL), and the reaction solution was stirred at room temperature overnight. The reaction solution was purified by LC-MS to obtain 12.0 mg of the title compound. The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 2.35 (s, 3H), 3.94 (s, 3H), 6.17 (d, J = 8.0 Hz, 1H), 6.79 (d, J = 16 Hz, 1H), 7.30-7.37 (m, 3H), 7.43-7.50 (m, 3H), 7.54-7.65 (m, 2H), 7.65 (d, J = 16 Hz, 1H), 7.70 (d, J = 8.4 Hz, 1H), 7.89 (d, J = 7.6 Hz, 2H), 8.80 (d, J = 8.0 Hz, 1H), 8.86 (s, 1H).

References: [1]Patent: EP2019094,2009,A1 .Location in patent: Page/Page column 106.

26
[ 5978-75-6 ]
[ 100-52-7 ]
[ 81532-35-6 ]

References: [1]Organic Letters,2008,vol. 10,p. 5429 - 5432.

27
[ 504-02-9 ]
[ 5978-75-6 ]
[ 1239619-81-8 ]

References: [1]Chemistry - A European Journal,2010,vol. 16,p. 7090 - 7095.

28
[ 37942-07-7 ]
[ 5978-75-6 ]
[ 1223561-32-7 ]

References: [1]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 1617 - 1621.

29
[ 1266229-00-8 ]
[ 5978-75-6 ]
[ 1266231-79-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 15h;	Methyl(3S,8aR)-2-[(2S)-2-[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate (200 mg) was dissolved in tetrahydrofuran (5.7 mL), a solution prepared by dissolving lithium hydroxide monohydrate (24.8 mg) in water (1.5 mL) were added thereto, and the mixture was stirred at 50 C. for 3 hr. To the mixture was added 1M hydrochloric acid (0.59 mL), and the mixture was concentrated under reduced pressure to give a colorless amorphous powder. This amorphous powder, 9H-fluorene-9-amine hydrochloride (103 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (339 mg) and 1-hydroxybenzotriazole (79.7 mg) were mixed in N,N-dimethylformamide (3 mL), and the mixture was stirred at room temperature for 15 hr. The mixture was diluted with ethyl acetate (30 mL), and washed with water (30 mL) and saturated brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/hexane=30/70?100/0) to give an amorphous powder. This amorphous powder was dissolved in ethyl acetate (4 mL), 4M hydrogen chloride-ethyl acetate solution (2 mL) was added thereto, and the mixture was stirred at room temperature for 3 hr. To the mixture were added ethyl acetate (10 mL) and saturated aqueous sodium hydrogen carbonate solution (30 mL), and the organic layer was separated, washed with saturated brine (30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (110 mg) as a white solid.LC-MS: 558.4 (MH+).1H NMR (DMSO-d6, 300 MHz): delta 0.87-1.27 (8H, m), 1.29-1.45 (1H, m), 1.52-1.89 (10H, m), 1.94-2.21 (6H, m), 2.79-3.04 (2H, m), 3.33-3.62 (2H, m), 4.08-4.17 (1H, m), 4.72-4.82 (1H, m), 5.06 (1H, d, J=3.2 Hz), 5.96-6.07 (1H, m), 7.26-7.64 (6H, m), 7.80-7.99 (3H, m), 8.33-8.55 (1H, m).

References: [1]Patent: US2011/34469,2011,A1 .Location in patent: Page/Page column 133.

30
[ 1376600-50-8 ]
[ 5978-75-6 ]
[ 1376600-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	General procedure: Z-Am8(S2Py)-OH (217 mg) was coupled with 1-naphthylamine (72 mg) in cooled DMF, and N-hydroxybenzotrizole (HOBt·H2O) (92 mg), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (228 mg), and N,N-diisopropylethylamine (DIEA) (87 muL) were added and stirred overnight. After the reaction had completed as monitored by TLC (CHCl3:CH3OH = 9:1) and HPLC, the DMF was evaporated and the residue was dissolved in ethyl acetate and washed with citric acid solution (10%), followed by sodium bicarbonate solution (4%) and brine, and then dried over anhydrous MgSO4. The remaining ethyl acetate was evaporated and the residue was purified by silica gel chromatography using a mixture of DCM and methanol (149:1) to yield compound 1 (256 mg, 91.5%; Overall yield: 46.1%) as a white solid.

References: [1]European Journal of Medicinal Chemistry,2012,vol. 52,p. 111 - 122.

31
[ 2157-52-0 ]
[ 5978-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; under 760.051 Torr;	First step, 9-fluorenone oxime (400 mg) and concentrated HCl (0.86 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (33 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield fluorenamine hydrochloride (240 mg) as a white solid. Second step, a mixture of fluorenamine (304 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-(fluorene-9-yl)-adenosine(208 mg) as a white solid: positive ESIMS m/z 432 [M + H]+ and 454 [M + Na]+; negative ESIMS m/z 430 [M - H]- and 466 [M + Cl]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.46. (1H, d, J = 8.1 Hz, -NH), 8.38 (2H, s, H-2, H-8), 5.94 (1H, d, J = 5.4 Hz, H-1), 5.52 (1H, d, J = 5.7 Hz, -OH), 5.44 (1H, m, -OH), 5.25 (1H, d, J = 4.8 Hz, -OH), 4.66 (1H, m, H-2'), 4.19 (1H, m, H-3'), 4.01 (1H, m, H-4'), 3.67 (1H, m, H-5'a), 3.56 (1H, m, H-5'b); the 9-fluorene moiety delta 7.86 (2H, d, J = 7.5 Hz, H-4", H-5"), 7.46 (2H, d, J = 7.5 Hz, H-1, H-8), 7.40 (2H, t, J= 7.5 Hz, H-2", H-7"), 7.26 (2H, t, J= 7.5 Hz, H-3", H-6), 6.69 (1H, d, J = 8.1 Hz, H-9"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 155.1 (s, C-6), 152.4 (d, C-2), 148.8 (s, C-4), 140.3 (d, C-8), 120.2 (s, C-5), 88.1 (d, C-1), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (t, C-5'); the 9-fluorene moiety delta 145.0 (s, C-8"a, C-9"a), 140.3 (s, C-4"a, C-5a ), 128.3 (d, C-1, C-8"), 127.5 (d, C-3", C-6"), 124.8 (d, C-2", C-7"), 120.2 (d, C-4", C-5"), 54.9 (d, C-9")o
240 mg	With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr;	First step, 9-fluorenone oxime (400 mg) and concentrated HCl (0.86 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (33 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield fluorenamine hydrochloride (240 mg) as a white solid.
240 mg	With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water;	weigh precisely 9-fluorenone oxime (400 mg) and add 10% Pd / C (33 mg) and concentrated hydrochloric acid (0.86 mL), dissolved in EtOH (50 mL), hydrogenated under atmospheric pressure , Filter the reaction solution, remove Pd / C, evaporate the filtrate, add ethyl acetate, mix well,Dissolve, filter to give pale yellow solid 9-fluorene hydrochloride (240 mg)

References: [1]Patent: EP2511283,2012,A1 .Location in patent: Page/Page column 92-93.
[2]Patent: US2013/45942,2013,A1 .Location in patent: Paragraph 0390.
[3]Patent: JP2015/172077,2015,A .Location in patent: Paragraph 0190.

32
[ 17216-08-9 ]
[ 5978-75-6 ]
C₂₅H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.8%		<strong>[5978-75-6]9-aminofluorene hydrochloride</strong> (0.020 mol) in anhydrous ethanol (100 mL),triethylamine (0.020 mol) was added at room temperature during 2 h and standing for0.5 h. The supernatant was allowed to react with a solution of 2-acetyl-1-tetralone(0.020 mol) and 0.7 mL acetic acid in anhydrous ethanol (100 mL) at the refluxingtemperature for 24 h. After refluxing with stirring for 24 h, the resulting mixture wascooled to room temperature to afford a yellow solid. The solid was recrystallized fromcold ethanol to get ligand L4 as a yellow crystal in 57.8% yield. Mp: 202-203 C. 1HNMR (CDCl3), delta (ppm): 13.01 (s, 1H), 7.43-7.95 (m, 8H), 7.16-7.32 (m, 4H), 5.67 (s,1H), 2.35-2.65 (m, 4H), 1.64 (s, 3H,). 13C NMR(CDCl3, delta, ppm): 184.23, 162.64,144.58, 141.08, 140.15, 135.99, 130.65, 128.75, 127.82, 127.05, 126.50, 126.36, 124.67,120.27, 101.76, 59.21, 29.25, 24.92, 15.56.

References: [1]Chemistry Letters,2016,vol. 45,p. 1232 - 1234.
[2]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 4695 - 4704.

33
[ 5978-75-6 ]
[ 2004-06-0 ]
[ 103450-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In propan-1-ol; at 70℃; for 8h;	First step, 9-fluorenone oxime (400 mg) and concentrated HCl (0.86 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (33 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield fluorenamine hydrochloride (240 mg) as a white solid. Second step, a mixture of fluorenamine (304 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-(fluorene-9-yl)-adenosine(208 mg) as a white solid: positive ESIMS m/z 432 [M + H]+ and 454 [M + Na]+; negative ESIMS m/z 430 [M - H]- and 466 [M + Cl]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.46. (1H, d, J = 8.1 Hz, -NH), 8.38 (2H, s, H-2, H-8), 5.94 (1H, d, J = 5.4 Hz, H-1), 5.52 (1H, d, J = 5.7 Hz, -OH), 5.44 (1H, m, -OH), 5.25 (1H, d, J = 4.8 Hz, -OH), 4.66 (1H, m, H-2'), 4.19 (1H, m, H-3'), 4.01 (1H, m, H-4'), 3.67 (1H, m, H-5'a), 3.56 (1H, m, H-5'b); the 9-fluorene moiety delta 7.86 (2H, d, J = 7.5 Hz, H-4", H-5"), 7.46 (2H, d, J = 7.5 Hz, H-1, H-8), 7.40 (2H, t, J= 7.5 Hz, H-2", H-7"), 7.26 (2H, t, J= 7.5 Hz, H-3", H-6), 6.69 (1H, d, J = 8.1 Hz, H-9"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 155.1 (s, C-6), 152.4 (d, C-2), 148.8 (s, C-4), 140.3 (d, C-8), 120.2 (s, C-5), 88.1 (d, C-1), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (t, C-5'); the 9-fluorene moiety delta 145.0 (s, C-8"a, C-9"a), 140.3 (s, C-4"a, C-5a ), 128.3 (d, C-1, C-8"), 127.5 (d, C-3", C-6"), 124.8 (d, C-2", C-7"), 120.2 (d, C-4", C-5"), 54.9 (d, C-9")o
208 mg	With triethylamine; In propan-1-ol; at 70℃; for 8h;	Second step, a mixture of fluorenamine (304 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60 ml) was heated to 70 C. and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20:1) to yield N6-(fluorene-9-yl)-adenosine (208 mg) as a white solid: positive ESIMS m/z 432 [M+H]+and 454 [M+Na]+; negative ESIMS m/z 430 [M-H]- and 466 [M+Cl]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.46 (1H, d, J=8.1 Hz, -NH), 8.38 (2H, s, H-2, H-8), 5.94 (1H, d, J=5.4 Hz, H-1'), 5.52 (1H, d, J=5.7 Hz, -OH), 5.44 (1H, m, -OH), 5.25 (1H, d, J=4.8 Hz, -OH), 4.66 (1H, m, H-2'), 4.19 (1H, m, H-3'), 4.01 (1H, m, H-4'), 3.67 (1H, m, H-5'a), 3.56 (1H, m, H-5'b); the 9-fluorene moiety delta 7.86 (2H, d, J=7.5 Hz, H-4", H-5"), 7.46 (2H, d, J=7.5 Hz, H-1", H-8'"), 7.40 (2H, t, J=7.5 Hz, H-2", H-7"), 7.26 (2H, t, J=7.5 Hz, H-3", H-6'"), 6.69 (1H, d, J=8.1 Hz, H-9"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 155.1 (s, C-6), 152.4 (d, C-2), 148.8 (s, C-4), 140.3 (d, C-8), 120.2 (s, C-5), 88.1 (d, C-1'), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (t, C-5'); the 9-fluorene moiety delta 145.0 (s, C-8"a, C-9"a), 140.3 (s, C-4"a, C-5"a), 128.3 (d, C-1", C-8"), 127.5 (d, C-3", C-6"), 124.8 (d, C-2", C-7"), 120.2 (d, C-4", C-5"), 54.9 (d, C-9").
208 mg	With triethylamine; In propan-1-ol; at 70℃; for 8h;	6-Chloropurine nucleoside (200 mg) and triethylamine (3 mL) were added to a solution of 9-fluorene hydrochloride (304 mg) and dissolved in propanol (60 mL)The mixture was heated to 70 C., reacted for 8 hours, and the solvent was recovered with a reaction solution. The residue was separated by silica gel column chromatography and washed with chloroform-methanol (20: 1) to obtain a white solid N6-(fluoren-9-yl)-adenosine (208 mg) is obtained

References: [1]Patent: EP2511283,2012,A1 .Location in patent: Page/Page column 93.
[2]Patent: US2013/45942,2013,A1 .Location in patent: Paragraph 0389; 0391.
[3]Patent: JP2015/172077,2015,A .Location in patent: Paragraph 0190.

34
[ 75178-96-0 ]
[ 5978-75-6 ]
[ 79-08-3 ]
C(NapN₉flene)3 [ No CAS ]

References: [1]European Journal of Organic Chemistry,2013,p. 3560 - 3566.

35
[ 5978-75-6 ]
[ 525-03-1 ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 4500 - 4503.
[2]Applied Organometallic Chemistry,2019,vol. 33.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 5978-75-6 ]

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Amines

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(S)-1-(Naphthalen-2-yl)propan-1-amine hydrochloride

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CAS No.: 5978-75-6

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