116530-60-0|5-Nitro-1H-inden-2(3H)-one| Ambeed

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Quality Control of [ 116530-60-0 ] Purity: 97% SDS Specification

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Product Details of [ 116530-60-0 ]

CAS No. :	116530-60-0
Formula :	C₉H₇NO₃
M.W :	177.16
SMILES Code :	O=C1CC2=C(C=C([N+]([O-])=O)C=C2)C1
MDL No. :	MFCD00598938
InChI Key :	VSEBFWRYDORZJI-UHFFFAOYSA-N
Pubchem ID :	1502066

Safety of [ 116530-60-0 ]

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

Computational Chemistry of [ 116530-60-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	48.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.31
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	1.14
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.26
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.	0.52
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	0.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.93
Solubility	2.07 mg/ml ; 0.0117 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.	-2.05
Solubility	1.56 mg/ml ; 0.00881 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	-2.5
Solubility	0.567 mg/ml ; 0.0032 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.57 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	2.0 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)	1.95

Application In Synthesis of [ 116530-60-0 ]

* 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 [ 116530-60-0 ]

[ 116530-60-0 ] Synthesis Path-Downstream 1~35

1
[ 615-13-4 ]
[ 116530-60-0 ]

Yield	Reaction Conditions	Operation in experiment
49.5%	With nitric acid; In chloroform; at -20℃; for 1h;	In the single neck 250ml flask was added 5.6g 2-indanone and 40mL chloroform. 13mL 95% fuming nitric acid was measured. Both will be placed in a low temperature bath cooled to below -20C. Cooled 2-indanone was slowly added cooled fuming nitric acid. The reaction system was stirred vigorously while adding dropwise for 40 minutes. After the addition was complete by TLC trace (developing solvent: chloroform:methanol = 100:1, product Rf = 0.64,2- indanone Rf = 0.79). The reaction was continued at -20C for 20 minutes until reaction completion. With 60mL 10% sodium hydroxide solution was mixed with ice water to quench the reaction. The reaction system presents two layers in a separating funnel. The upper layer was extracted with chloroform (3 × 30mL). The combined organic phases was washed with saturated brine until neutral. The organic solvent was evaporated by a rotary evaporator to give a yellow solid. Recrystallization using ethyl acetate and cyclohexane then cooling gave reddish-brown crystals. Filtration gave 3.8g 5-nitro-2-indanone, yield 49.5%, mp 141-143C.
49.5%	With nitric acid; In chloroform; at -20℃;	It has been reported that 2-indanone is able to convert to 5-nitro-2-indanone by fuming nitric acid with vigorous stirring at -20 C according to modified published methodology [36] . To a cooled solution of 5.6 g 2-indanone in 40 mL chloroform was dropped slowly with 13 mL fuming nitric acid with vigorous stirring in 45 min at -20 C. After the addition was completed, the mixture was then stirred further for 20 min, poured into a mixture of sodium hydroxide (6.5 g) in water and ice (ca. 50 mL), and then extracted twice with ethyl acetate. The combined extracts were washed with water until neutral, dried over magnesium sulfate, and evaporated in vacuum to yield yellow solid. Chloroform was used as the eluent in column chromatography. Finally, the crude product was recrystallized from ethyl acetate/hexane to give 3.7 g of product (49.5% yield). m.p.:142-144 C (lit [36] 141-143 C).

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 12722 - 12726.
[2]Patent: CN105315204,2016,A .Location in patent: Paragraph 0028; 0032; 0033.
[3]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.
[4]Chemische Berichte,1899,vol. 32,p. 28,31.

2
[ 7697-37-2 ]
[ 615-13-4 ]
[ 116530-60-0 ]

References: [1]Chemische Berichte,1899,vol. 32,p. 28,31.

3
[ 116530-60-0 ]
[ 7697-37-2 ]
[ 610-27-5 ]

References: [1]Chemische Berichte,1899,vol. 32,p. 28,31.

4
[ 116530-60-0 ]
[ 16513-67-0 ]

Yield	Reaction Conditions	Operation in experiment
83%		Example 1: 4-[4-(2-Hydroxy-indan-5-yl)-5-mercapto-4H-[1 ,2,4]triazol-3-yl]- 6-isopropyl-benzene-1,3-diol (Compound 4) <n="206"/>Scheme 15-nitro-indan-2-ol (b, Scheme 1)<strong>[116530-60-0]5-nitro-2-indanone</strong> (5.3g, 30mmol) was dissolved in EtOH: /-PrOH (1:1 , 15OmL). NaBH4 (1.7g, 45mmol) was added portion by portion at room temperature. The reaction mixture was stirred at r.t for additional 30 min and water was added at 0 0C (ice-water bath). The reaction mixture was extracted with EtOAc (10OmL x 3) and the combined organic layers were washed with water and brine and dried over Na2SO4. Purification of the concentrated crude product by column chromatography (EtOAc: Hexane = 4:6) afforded the title product as a pale yellow oil (4.47 g, 83%).
500 mg	With methanol; sodium tetrahydroborate; at 0℃; for 1h;	To a stuffed solution of <strong>[116530-60-0]5-nitroindan-2-one</strong> (500 mg, 2.824 mmol) in methanol (10 mL) was added sodium borohydride (215 mg, 5.648 mmol) at 0 C portionwise. The reaction mixture was allowed to stir at 0 C for 1 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The crude compound was diluted with water (200 mL) and extracted with EtOAc (2x250 mL). The combined organic layer was dried over sodium sulfate and concentrated to afford 5- nitroindan-2-ol (500 mg) which was taken to the next step without further purification.

References: [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.
[2]Patent: WO2007/139955,2007,A2 .Location in patent: Page/Page column 204-205.
[3]Patent: WO2015/58084,2015,A1 .Location in patent: Paragraph 0448.

5
[ 116530-60-0 ]
[ 107-21-1 ]
[ 959838-22-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	toluene-4-sulfonic acid; In benzene; at 95℃;	Example 7: [4-(1',3'-Dihydro-spiro[[1 ,3]dioxolane-2,2'-inden]-5'-yl)-5- mercapto-4H-[1 ,2,4]triazol-3-yl]-6-isopropyl-benzene-1 ,3-diol (Compound 10)Scheme 35MSlitro-13'-dihydro-spiro[[1,3]dioxolane-2,2'-indene (e, Scheme3)<strong>[116530-60-0]5-nitro-2-indanone</strong> (620mg, 3.5 mmol) and p-TsOH (67mg, cat. amount) was charged into two-neck 10OmL r.b.f . Benzene (3OmL) was added followed by ethylene glycol (0.29 mL, 5.25mmol). The reaction mixture was refluxed at 95 0C over night with dean stark equipped. After cooled to room temperature, water was added and the reaction mixture was extracted with EtOAc. Combined organic layers were washed with water and brine and dried over Na2SO4. Purification of the concentrated crude product by column chromatography (EtOAc: Hexane = 2:8) afforded the title product as a pale yellow solid (660mg, 85%).

References: [1]Patent: WO2007/139955,2007,A2 .Location in patent: Page/Page column 208.

6
[ 116530-60-0 ]
[ 124-40-3 ]
dimethyl-(5-nitro-1H-inden-2-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrahydrofuran; at 20℃; for 0.5h;	Example 16: 4-[4-(2-Dimethylamino-indan-5-yl)-5-hydroxy-4H-[1 ,2,4]triazol- 3-yl]-6-isopropyl-benzene-1 ,3-diol (Compound 24)Scheme 6 <n="214"/>Dimethyl-(5-nitro-indan-2-yl)-amine (g, Scheme 6)To a solution of <strong>[116530-60-0]5-nitro-2-indanone</strong> (885 mg, 5 mmol) in THF (15mL) was added dimethylamine (2N in THF, 5 ml_, 10 mmol) dropwise. The reaction mixture was stirred at r.t. for 5 h. Water was added and the reaction mixture was extracted with EtOAc. Combined organic layers were washed with water and brine and dried over Na2SO4. The concentrated crude product was filtered through a short pad of silica gel (EtOAc:hexane =1 :1) and the filtrate was concentrated to give dimethyl-(5-nitro-1 H-inden-2-yl)-amine as a dark red solid (1.0 g, 98%).

References: [1]Patent: WO2007/139955,2007,A2 .Location in patent: Page/Page column 212-213.

7
[ 71720-52-0 ]
[ 116530-60-0 ]

References: [1]Chemische Berichte,1899,vol. 32,p. 28,31.

8
[ 90649-71-1 ]
[ 116530-60-0 ]

References: [1]Chemische Berichte,1899,vol. 32,p. 28,31.

9
[ 24424-99-5 ]
[ 116530-60-0 ]
(2-oxo-indan-5-yl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; at 50℃; under 5171.62 Torr; for 12.5h;	5-Nitro-2-indanone (100mg), di-tert-butyldicarbonate (135mg), palladium on carbon [(15MG),] 3A powdered molecular sieves (30mg) and THF (10ml) were combined in a Parr vessel, which was purged with hydrogen gas at 100psi and heated to [50C] for 12.5 hours. The mixture was filtered through a pad of celite, washing through with THF. The solvent was removed in vacuo and the residue triturated with diethyl ether to yield the title compound as a mustard coloured solid (66mg, 48%). TLC Rf 0.59 [(ETOAC/HEPTANE). 1H] NMR [300MHZ] (d6-DMSO) 9.12 (1H, s, br), 7.27 (1H, s), 7.06 (1H, d), 6.97 (1H, d), 3.3 (2H, s), 3.24 (2H, s), 1.27 (9H, s).

References: [1]Patent: WO2004/22554,2004,A1 .Location in patent: Page 48.

10
[ 667939-87-9 ]
[ 116530-60-0 ]
7'-methoxy-3'-methyl-5-nitro-6'-(1,3-oxazol-5-yl)-1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	toluene-4-sulfonic acid; In DMF (N,N-dimethyl-formamide); at 110℃; for 0.5h;Microwave reactor;	To a stirred solution of Intermediate 1 (200mg) and PTSA [(1.] 0mg) in DMF (5 [ML)] was added <strong>[116530-60-0]5-nitro-2-indanone</strong> (430mg). The reaction mixture was heated to [110C] for 30 mins in a microwave reactor and allowed to cool. The solvent was removed in vacuo and the residue purified by column chromatography on silica eluting with 70% EtOAc/heptane followed by 5% MeOH/DCM to afford the title compound as a brown solid (252mg, 77%). TLC Rf 0.68 (EtOAc). LCMS 407 [[M+H] +,] RT 3.15 [MINS.'H] NMR [300MHZ] (d6-DMSO) 8.55 (1H, s), 8.17 (1H, s), 8.15 (1H, dd), 8.05 (1H, s), 7.65 (1H, s), 7.55 (1H, d), 7.35 (1H, s), 6.37 (1H, s), 3.9 (3H, s), 3.8 (1H, d), 3.7 (1H, d), 3.35 (1H, d), 3.27 (1H, d), 2.95 (3H, s).

References: [1]Patent: WO2004/22554,2004,A1 .Location in patent: Page 54.

11
Å molecular sieves [ No CAS ]
[ 116530-60-0 ]
[ 100-46-9 ]
5-nitro-2-(phenylmethyl)aminoindane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol;	(b) 5-Nitro-2-(phenylmethyl)aminoindane 5-Nitro-2-indanone (1.48 g, 8.36 mmol), benzylamine (4.40 ml, 41.8 mmol), acetic acid (15.0 ml), 4 A molecular sieves (20 ml), THF (15 ml), and MeOH (15 ml) were introduced into a flask and cooled to 0 C. Sodium cyanoborohydride (1.05 g, 16.7 mmol) was then added portionwise over a 5-minute period. The mixture was stirred for 14 hr, filtered through celite, and concentrated to a syrup. The mixture was made basic with 2N NaOH and extracted with ether (3*50 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered, concentrated and chromatographed over silica gel (3% methanol/methylene chloride) to yield 5-nitro-2-(phenylmethyl)aminoindane: (1.18 g, 53%); M.S. (M+H)+ =269.

References: [1]Patent: US5807886,1998,A .

12
[ 110-91-8 ]
[ 116530-60-0 ]
C₁₃H₁₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 5h;Heating / reflux;	Morpholine (0.13 mL, 1.5 mmol) was added to a suspension of nitroindanone (177 mg, 1.00 mmol) in 10 mL of toluene. The mixture was heated to reflux with stirring. A dark solution was obtained, and water was seen collecting in the condenser. After 3h the solution was cooled. An aliquot was evaporated to dryness and the enamine was verified by 1H NMR. A dark solid separated from the solution on cooling. The bulk reaction mixture was evaporated to remove most of the solvent. 5 mL of methanol was added, which did not dissolve solid residue. 5 mL CH2Cl2 was added, which did dissolve most of the material. NaBH3CN (62.8 mg, 1.00 mmol) was added, followed by HOAc (1.00 mL). Stirring was continued overnight. Evaporated the solvent to dryness and partitioned the resulting residue between Na2CO3 and CH2Cl2. The aqueous phase was extracted with more CH2Cl2. The combined organic layers were dried over MgSO4 and evaporated. The residue was purified by column chromatography, CH2Cl2/Me0H gradient 1-10%, isolateing 215 mg of 4-(5-nitro-indan-2-yl)-morpholine as a tan crystalline solid.To a solution of 4-(5-nitro-indan-2-yl)-morpholine (210 mg, 0.85 mmol) in 20 mL of methanol was added Pd/C 10% (20 mg). The mixture was placed under a H2 atmosphere with stirring for 2 h. TLC showed 2 spots. CH2Cl2 was added to dissolve the ppt. that had <n="161"/>formed and the hydrogenation continued further 2h. The catalyst was removed by filtering, and the filtrate evaporated to give 188mg of 2-morpholin-4-yl-indan-5-ylamine. The crude amine was used in the next step without purification.To a suspension of the 3-[(3,4-dimethoxy-benzoylamino)-methyl]-benzoic acid (100 mg, 0.32 mmol) and 2-morpholin-4-yl-indan-5-ylamine (84 mg, 0.38 mmol) 1.5 mL of DMF. To this was added TBTU (122 mg, 0.38 mmol), and the vial warmed until a clear solution was obtained. The solution was stirred at room temperature. Stirring continued for 20 h total. Diluted with EtOAc and washed with Na2CO3, water and brine. The organic layer was dried over MgSO4, evaporated and purified by column chromatography, CH2Cl2/Me0H gradient 1-10%, to give 103 mg of 3,4-dimethoxy-iV-[3-(2-morpholin-4-yl- indan-5-ylcarbamoyl)-benzyl]-benzamide. MS, electrospray, 516, (M+H).

References: [1]Patent: WO2008/86047,2008,A1 .Location in patent: Page/Page column 158-160.

13
[ 116530-60-0 ]
[ 124-40-3 ]
[ 895637-34-0 ]

Yield	Reaction Conditions	Operation in experiment
94%		To a stined solution of <strong>[116530-60-0]5-nitro-1H-inden-2(3H)-one</strong> (1 g, 5.65 mmol) in DCM (15 mL) was added AcOH (1.6 mL, 28.25 mmol) followed by N,N-dimethylamine (2M in THF) (5.6 mL, 11.30 mmol) at 0 C. After 15 mins, NaCNBH3 (4.79 g, 22.60 mmol) was added. The ice bath was removed, and the reaction was stined at RT for 16 h. The reaction was concentrated, diluted with water, and the pH was adjusted to 11 with iN NaOH. The mixture was extracted with 5% MeOH:DCM (2 x 300 mL). The combined organic layers were washed with water (15 mL), dried (Na2504) and concentrated to afford N,N-dimethyl-5- nitro-2,3-dihydro-1H-inden-2-amine (1.1 g, 94%) as a dark oil; MS (LCMS) mlz 207.0.
		A 100 ml flask charged with 5-nitro-lH-inden-2(3H)-one (1 g, 5.64 mmol), dichloromethane (28 ml) and acetic acid (1.616 ml, 28.2 mmol). The resulting solution was cooled in an ice bath and dimethylamine, 2M in tetrahydrofuran (5.64 ml, 1 1.29 mmol) was added dropwise. After warming to ambient temperature, the reaction was stirred 15 minutes. Sodium triacetoxyborohydride (4.8 g, 22.6 mmol) was added and the reaction was stirred 72 hours. The reaction was concentrated and the residue was partitioned between methylene chloride (100 ml) and water (100 ml). The pH was adjusted to ca. 11 with 1 M sodium hydroxide, the layers were separated and the aqueous layer extracted with methylene chloride. The combined organics were washed with brine (200 ml), dried over sodium sulfate, filtered and concentrated and the residue was purified on a funnel plug of silica gel (150 g) eluted with 1, 2.5, and 5% methanol in methylene chloride to provide the title compound. MS (DCI) m/e 207 (M+H)+.

References: [1]Patent: WO2019/28008,2019,A1 .Location in patent: Paragraph 0196.
[2]Patent: WO2011/53476,2011,A1 .Location in patent: Page/Page column 197-198.

14
[ 116530-60-0 ]
5-nitro-2,3-dihydro-1H-inden-2-yl methanesulfonate [ No CAS ]

References: [1]Patent: WO2015/58084,2015,A1 .
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.

15
[ 116530-60-0 ]
5-amino-2,3-dihydro-1H-inden-2-yl methanesulfonate [ No CAS ]

References: [1]Patent: WO2015/58084,2015,A1 .
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.

16
[ 116530-60-0 ]
1-(5-aminoindan-2-yl)-3-iodo-3H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

References: [1]Patent: WO2015/58084,2015,A1 .

17
[ 116530-60-0 ]
5-[4-amino-1-(5-amino-2,3-dihydro-1H-inden-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2,3-difluorophenol [ No CAS ]

References: [1]Patent: WO2015/58084,2015,A1 .

18
[ 116530-60-0 ]
1-(5-nitro-2,3-dihydro-1H-inden-2-yl)piperazine [ No CAS ]

References: [1]Patent: EP2632465,2015,B1 .

19
[ 116530-60-0 ]
[ 57260-71-6 ]
tert-butyl 4-(5-nitro-2, 3-dihydro-1H-inden-2-yl) piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In methanol;	To a solution of 5-nitro-indene-2-one (1.0 g, 5.6 mmol) in methanol (40 mL) containing a stir bar was added sodium cyanoborohydride (1.7 g, 28 mmol) and N-Boc piperazine (1.6 g, 8.5 mmol) followed by addition of few drops of acetic acid; the resulting mixture was stirred for overnight. Analysis of the reaction mixture by LC indicated that reaction had gone to completion. The solution was concentrated in vacuo and the resulting crude was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, and brine, then dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was then subjected for purification by silica gel column chromatography (5% MeOH in DCM) to provide tert-butyl 4-(5-nitro-2, 3-dihydro-1H-inden-2-yl) piperazine-1-carboxylate. LC-MS (IE, m/z): 348 [M+1]+. The material was further treated with TFA to remove the Boc group. Removal of volatiles gave rise to 1-(5-nitro-2,3-dihydro-1H -inden-2-yl)piperazine, which was used without further purification.

References: [1]Patent: EP2632465,2015,B1 .Location in patent: Paragraph 0114.

20
[ 1255208-69-5 ]
[ 116530-60-0 ]
1-(5-nitro-2,3-dihydro-1H-inden-2-yl)-4-[2-(4-nitrophenyl)ethyl]piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) isopropylate; sodium cyanoborohydride; at 20℃; for 3h;	A mixture of 1-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride (50 mg, 0.18 mmol), <strong>[116530-60-0]5-nitro-1,3-dihydro-2H-inden-2-one</strong> (39 mg, 0.22 mmol), sodium cyanoborohydride (58 mg, 0.92 mmol, and Titanium (IV) Isopropoxide (0.54 mL, 1.8 mmol) was allowed to stir at RT for 3 hours. LC showed formation of the desired product. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, filtered, concentrated and purified by mass-directed HPLC (0.1% TFA in water and acetonitrile). LC-MS (IE, m/z): 397 (M+1)+. (0.31 muM)

References: [1]Patent: EP2632465,2015,B1 .Location in patent: Paragraph 0334.

21
[ 116530-60-0 ]
5-nitro-2-indanone oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.7%	With ethanol; water; hydroxylamine; In pyridine; at 20℃; for 3.5h;	At room temperature, 4g <strong>[116530-60-0]5-nitro-2-indanone</strong> dissolved in 20mL pyridine gave a dark brown color solution. to this was added 2.16g of hydroxylamine 1.6ml of water and 5ml of anhydrous ethanol. The reaction was stirred at room temperature for 3 hours. Excess of water was added to the system after the end of the reaction and stirring was continued for 30 minutes. Suspension reaction solution was filtered to give brick-red filter cake. The filter cake was washed several times with water until no more color lighter. The filter cake was recrystallized from 60% aqueous ethanol and dried to give 3.2g <strong>[116530-60-0]5-nitro-2-indanone</strong> oxime, yield 72.7%, mp of 171-173C.
72.7%	With pyridine; hydroxylamine; In ethanol; water; at 20℃;	To a stirring solution of 4 g <strong>[116530-60-0]5-nitro-2-indanone</strong> in 20 mL pyridine was added with the solution of 2.2 g hydroxylamine in 5 mL ethanol and 2 mL water at room temperature in 5 min, with further stirring for 3 h 100 mL water was added to the flask and stirred for half an hour. The mixture was then filtered to give yellow crystal. The crude product was recrystallized from ethanol/water (60%) to obtain 3.7 g product (72.7% yield). m.p.: 173-175 C.

References: [1]Patent: CN105315204,2016,A .Location in patent: Paragraph 0028; 0034; 0035.
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.

22
[ 116530-60-0 ]
7-nitro-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]

References: [1]Patent: CN105315204,2016,A .
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.

23
[ 116530-60-0 ]
7-amino-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]

References: [1]Patent: CN105315204,2016,A .
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.

24
[ 116530-60-0 ]
N-(3-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide [ No CAS ]

References: [1]Patent: CN105315204,2016,A .
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.

25
[ 116530-60-0 ]
N-(2-benzoyl-3-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide [ No CAS ]

References: [1]Patent: CN105315204,2016,A .
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.

26
[ 95-13-6 ]
[ 116530-60-0 ]

References: [1]Patent: CN105315204,2016,A .
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 738 - 747.

27
[ 116530-60-0 ]
5-amino-2,3-dihydro-1H-inden-2-yl methanesulfonate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.

28
[ 116530-60-0 ]
5-amino-2,3-dihydro-1H-inden-2-yl methanesulfonate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.

29
[ 116530-60-0 ]
5-amino-2,3-dihydro-1H-inden-2-yl methanesulfonate hydrochloride [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.

30
[ 116530-60-0 ]
5-amino-2,3-dihydro-1H-inden-2-yl methanesulfonate hydrochloride [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1161 - 1166.

31
[ 116530-60-0 ]
2-methoxy-N-(3-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide [ No CAS ]