Name: 34698-41-4|2,3-Dihydro-1H-inden-1-amine|98%
Brand: Ambeed
SKU: A126079
Price: 7.0 USD
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1
[ 4530-20-5 ]
[ 34698-41-4 ]
[ 74814-24-7 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1113 - 1122

2
[ 68253-35-0 ]
[ 34698-41-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia; hydrogen; In methanol; at 42℃; under 2625.26 Torr; for 20h;	Example 2 Preparation of racemic 1-aminoindan A reactor was charged at 25 C with 585.8 g of 1-indanone oxime and 4960 ml of 4.2 M ammonia in methanol, then to the reactor 117 g Catalyst Raney Ni ( in the form of suspension in methanol ) was added and the mixture was hydrogenated under stirring at constant pressure of 3.5 ± 0.1 bar . The hydrogenation reaction was carried out at a temperature of 42 ± 2 C for 20 hours . After completion of the reaction, the reaction mixture was cooled to 25 ± 2 C, the suspension was filtered to separate the catalyst . The filtrate was concentrated under reduced pressure and at a temperature of less than 40 C to constant weight to obtain 558. Og of an oily product . Assay : 95.1% HPLC, molar yield wass 100% . The product was kept in an inert atmosphere, at temperatures below 10 C and protected from light . Example 3: Preparation of diastereomeric salt (R, S) -1-aminoindan N- acetyl-L-glutaminate (1:1)
100%	With ammonia; hydrogen; In methanol; at 40 - 44℃; under 2550.26 - 2700.27 Torr; for 20h;	The reactor was charged at 25 C with 585.8 g 1-indanone oxime and 4960 mL of 4.2 M ammonia in methanol, after which 117 g of Raney Ni were added to the reactor in the form of a suspension in methanol . The mixture was hydrogenated under stirring at a constant pressure of 3.5 ± 0.1 bar . The hydrogenation reaction was carried out at a temperature of 42 ± 2 C for 20 hours . After completion of the reaction, the reaction mixture was cooled to 25 ± 2 C and the suspension was filtered to separate the catalyst . The filtrate was concentrated under reduced pressure at a temperature of less than 40 C to constant weight . 558.0 g of an oily product were obtained (assay : 95.1% HPLC, molar yield 100%) . The product was stored in an inert atmosphere at a temperature below 10 C and protected from light .
	With ammonia; hydrogen;Raney nickel; In methanol; at 10 - 42℃;Autoclave;	(B) Preparation of 1-Aminoindane racemic1.5 Kg pressured ammonia gas purged into 2500 mL methanol to obtain 20 to 25% ammonia solution in 5.0 L autoclave at 10C to 15C. The oxime (300 g, 1.0 mole), Raney nickel catalyst (75 g) were added and the mixture hydrogenated at a constant pressure of 5 Kg pressure. A nearly theoretical amount of hydrogen had been absorbed after 24 to 30 hours at 40C. The temperature range during hydrogenation was 40C-42C. The filtered methanol solution was concentrated on the rotary evaporator (maximum bath temperature, 40C). The residue was extracted in 1000 mL methylene dichloride. The solution was cooled and acidified with cone. HC1 (10%) to adjust the pH 4 to 5. The separated aqueous layer washed with methylenedichloride was further basified with 40% sodium hydroxide to adjust the pH 9.5 to 10 at 15C. The separated aqueous layer was further extracted with methylene dichloride. The separated organic 95%.

Reference： [1]Patent: WO2015/70995,2015,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2016/116607,2016,A1 .Location in patent: Page/Page column 23
[3]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 3448 - 3452
[4]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 3323 - 3326
[5]Organic Process Research and Development,2014,vol. 18,p. 1169 - 1174
[6]Synthesis,1980,p. 695 - 697
[7]Journal of Medicinal Chemistry,1980,vol. 23,p. 184 - 193
[8]Angewandte Chemie - International Edition,2020,vol. 59,p. 3900 - 3904
Angew. Chem.,2020,vol. 132,p. 3928 - 3932,5
[9]Journal of Organic Chemistry,2019,vol. 84,p. 4856 - 4866
[10]Journal of Medicinal Chemistry,1977,vol. 20,p. 771 - 776
[11]Journal of the Chemical Society. Perkin transactions I,1998,p. 3459 - 3462
[12]Patent: WO2012/153349,2012,A2 .Location in patent: Page/Page column 29

3
[ 31972-52-8 ]
[ 34698-41-4 ]
[ 74814-18-9 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1113 - 1122

4
[ 34698-41-4 ]
[ 135498-85-0 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 6800 - 6803
[2]European Journal of Medicinal Chemistry,1991,vol. 26,p. 167 - 178

5
[ 1502-03-0 ]
[ 34698-41-4 ]
[4-[[N-(4-benzylsulfanyl-6-chloro-[1,3,5]triazin-2-yl)-N-cyclohexylamino]methyl]-3,5-dimethoxyphenoxy]methyl-polystyrene resin [ No CAS ]
N-cyclododecyl-N'-cyclohexyl-N''-indan-1-yl-[1,3,5]triazine-2,4,6-triamine [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 117 - 120

6
[ 645-12-5 ]
[ 34698-41-4 ]
[ 37542-55-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃; for 14h;	5-Nitro-2-furan carboxylic acid (300 mg, 1.9 MMOL) and 1-amino-indane (246 muL, 1.9 MMOL) in DMF (5 mL) was treated with EDCI (730 mg, 3.8 MMOL) followed by DMAP (582 mg, 4.7 MMOL). The reaction mix was stirred for 14 hr. at room temperature and worked up as explained in general procedure afford 415 mg of product (80% yield). TLC: Rf 0.75 (1: 1 hexane: ethyl acetate) ;'H NMR (300 MHz, CDC13) : ES1. 95-2.1 (1H, m), 2.62-2. 76 (1H, m), 2. 88-3. 02 (1H, m), 3.03-3. 17 (1 H, m), 5.67 (1 H, q, J 6.75 Hz, 13.5 Hz), 6. 88-6. 97 (1 H, bd, J = 6.75 Hz), 7.22- 7.39 (m6Hs, M) ; 13C NMR (300 MHz, CDCl3) : 29.77, 33.14, 54.36, 111.9, 115.53, 123.64, 124. 48, 126.45, 127.92, 141.42, 142. 98, 147. 51, 155.50 ; El- Mass: 370.9 (M+-1).

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5276 - 5283
[2]Patent: WO2005/7625,2005,A2 .Location in patent: Page 41-42

7
[ 34698-41-4 ]
[ 117918-23-7 ]
[ 858780-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid With triethylamine; chlorophosphoric acid diphenyl ester In ethyl acetate at 20℃; for 1h; Stage #2: 2,3-dihydro-1H-inden-1-amine With triethylamine In ethyl acetate at 20℃; for 6h;

Reference： [1]Abdel-Rahman, Hamdy M.; El-Koussi, Nawal A.; Alkaramany, Gamal S.; Youssef, Adel F.; Kiso, Yoshiaki [Archiv der Pharmazie, 2004, vol. 337, # 11, p. 587 - 598]

8
[ 2398-37-0 ]
[ 34698-41-4 ]
N-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 9306 - 9307

9
[ 3938-96-3 ]
[ 34698-41-4 ]
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide [ No CAS ]

Reference： [1]ACS Catalysis,2020,p. 1375 - 1380
[2]Organic Letters,2007,vol. 9,p. 1157 - 1159

10
[ 34698-41-4 ]
[ 141-78-6 ]
[ 169105-02-6 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1157 - 1159

11
[ 3095-95-2 ]
[ 34698-41-4 ]
[ 870837-22-2 ]

Yield	Reaction Conditions	Operation in experiment
		After adding thionyl chloride (6.07 g) to a methylene chloride (20 mL) solution of diethoxyphosphoryl acetic acid (5.00 g), this reaction mixture was agitated at room temperature for 2 hours and the reaction solution was concentrated under reduced pressure. THF (40 mL) solution of the obtained residue was added dropwise to a THF (80 mL) solution of 1-aminoindane (3.40 g) and TEA (3.5 mL) under ice-cooling, and the reaction solution was agitated at the temperature. Water and ethyl acetate were added to this reaction mixture, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate system), and 4.2 g of the title compound was obtained. 1H-NMR (CDCl3) delta (ppm): 1.31-1.36 (m, 6H), 1.79-1.89 (m, 1H), 2.56-2.63 (m, 1H), 2.83-3.03 (m, 4H), 4.09-4.18 (m, 4H), 5.47 (q, J=7.6 Hz, 1H), 6.83-6.89 (brd, 1H), 7.19-7.32 (m, 4H).

Reference： [1]Patent: US2006/4013,2006,A1 .Location in patent: Page/Page column 50

12
[ 34698-41-4 ]
[ 814-68-6 ]
[ 870837-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0℃; for 0.333333h;	A THF (10 mL) solution of acrylic acid chloride (2.04 g) was added dropwise to a THF (30 mL) solution of 1-aminoindane (3.00 g) and TEA (2.28 g) under ice-cooling, and the reaction solution was agitated for 20 minutes at the temperature. Water and ethyl acetate were added to this reaction mixture, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 2.23 g of the title compound was obtained by adding ether to the residue and filtering insoluble matter. 1H-NMR (CDCl3) delta (ppm): 1.81-1.90 (m, 1H), 2.61-2.69 (m, 1H), 2.86-3.05 (m, 2H), 5.58 (q, J=7.6 Hz, 1H), 5.68 (dd, J=1.6 Hz, 10.4 Hz, 1H), 5.70-5.78 (brs, 1H), 6.10 (dd, J=10.4 Hz, 17.2 Hz, 1H), 6.34 (dd, J=1.6 Hz, 17.2 Hz, 1H), 7.20-7.32 (m, 4H).

Reference： [1]Cell Chemical Biology,2019,vol. 26,p. 1027 - 22,1035
[2]Patent: US2006/4013,2006,A1 .Location in patent: Page/Page column 54

13
5-nitro-2-furan carboxylic acid [ No CAS ]
[ 34698-41-4 ]
[ 37542-55-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; In N,N-dimethyl-formamide;	5-Nitro-furan-2-carboxylic acid indan-1-ylamide (26). 5-Nitro-2-furan carboxylic acid (300 mg, 1.9 mmol) and 1-amino-indane (246 muL, 1.9 mmol) in DMF (5 mL) was treated with EDCl (730 mg, 3.8 mmol) followed by DMAP (582 mg, 4.7 mmol). The reaction mix was stirred for 14 hr. at room temperature and worked up as explained in general procedure afford 415 mg of product (80% yield). TLC: Rf 0.75 (1:1 hexane:ethyl acetate); 1H NMR (300 MHz, CDCl3): delta1.95-2.1 (1H, m), 2.62-2.76 (1H, m), 2.88-3.02 (1H, m), 3.03-3.17 (1H, m), 5.67 (1H, q, J 6.75 Hz, 13.5 Hz), 6.88-6.97 (1H, bd, J=6.75 Hz), 7.22-7.39 (m6Hs, m); 13C NMR (300 MHz, CDCl3): 29.77, 33.14, 54.36, 111.9, 115.53, 123.64, 124.48, 126.45, 127.92, 141.42, 142.98, 147.51, 155.50; EI-Mass: 370.9 (M+-1).

Reference： [1]Patent: US2005/222408,2005,A1

14
[ 17640-21-0 ]
[ 34698-41-4 ]
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5581 - 5584
[2]European Journal of Organic Chemistry,2007,p. 5416 - 5421
[3]Organic Process Research and Development,2014,vol. 18,p. 1169 - 1174

15
formyl succinonitrile potassium salt [ No CAS ]
[ 34698-41-4 ]
[ 648893-27-0 ]

Yield	Reaction Conditions	Operation in experiment
37%		Reference Example 91-(Indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile Formyl succinonitrile potassium salt (36.5 g) and 1-aminoindane (36.6 g) were dissolved in water (100 ml), and acetic acid (100 ml) was added thereto. After agitating the mixture at 100C for 30 minutes, the reaction solution was poured into water (1200 ml). The reaction mixture was made basic by adding potassium carbonate and then extracted with ethyl acetate. After the organic layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure and the residue (37.4 g) was dissolved in ethanol (450 ml). After potassium ethoxide (35.2 g) was added thereto and the mixture was stirred at room temperature for 30 minutes, the reaction solution was poured into iced water (1500 ml) and extracted with ethyl acetate. After the organic layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography eluting with ethyl acetate-hexane (1 : 2, v/v) and the fractions were concentrated under reduced pressure to give 2-amino-1-(indan-1-yl)pyrrole-4-carbonitrile (20.4 g, 37%) as oily matter. To a solution of 2-amino-1-(indan-1-yl)pyrrole-4-carbonitrile (19.4 g), acetylacetone (9.6 g) and ethanol (375 ml) was added concentrated hydrochloric acid (3 ml), and the mixture was heated under reflux for 3 hours. The reaction solution was concentrated under reduced pressure and an aqueous sodium hydrogen carbonate solution was added to the residue, which was extracted with ethyl acetate. After the organic layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure and the crystal was collected by filtration to give 1-(indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (11.4 g, 46%).

Reference： [1]Patent: EP1535922,2005,A1 .Location in patent: Page/Page column 31

16
[ 603999-16-2 ]
[ 34698-41-4 ]
ethyl (9aS)-4-{4-[(2,3-dihydro-1H-inden-1-ylamino)carbonyl]-2-thienyl}-2-[2-(4-fluorophenyl)ethyl]-5-oxo-7,8,9,9a-tetrahydro-5H-pyrido[2,3-a]pyrrolizine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 14h;	D. 5- {(9aS)-3-(ethoxycarbonyl)-2[2-(4-fluorophenyl)ethyl]-5-oxo-7, 8,9, 9a- tetrahydro-5H-pyrido [2,3-a] pyrrolizin-4-yl}-3-thiophenecarboxylic acid (0.100 g, 0.202 mmol) was dissolved in CH2C12. 1-aminoindane (0.039 mL, 0.328 mmol) was added followed by EDCI (0.047 g, 0.243 mmol) and HOBt (0.033 g, 0. 243 mmol). After 14 h of stirring at ambient temperature the reaction mixture was poured onto 5% HCl solution and extracted with CH2C12. The organics were washed with sat'd NaHC03, brine and then dried (Na2SO4), filtered and concentrated to a brown residue. Chromatography on silica gel using 3: 1 EtOAc: Hexanes eluted the product to provide the title compound upon concentration as a white solid (0. 085 g, 0. 139 mmol, 69% yield) :'H NMR (CDC13, 400 MHz) 8 8.08 (s, 1H), 7.46 (s, 1H), 7. 35-7.31 (m, 1H), 7.28-7. 20 (m, 3H), 7.16 (dd, J= 8.5, 5. 5 Hz, 2H), 6.97 (t, 2H), 6.17 (m, 1H), 5.67 (dd, J= 15.5, 7.8 Hz, 1H), 4.69 (dd, J= 10.4, 6.2 Hz, 1H), 4.19 (dd, J= 14.3, 7.0 Hz, 2H), 3.76-3. 69 (m, 1H), 3.42-3. 36 (m, 1H), 3.19-2. 99 (m, 5H), 2.96-2. 87 (m, 1H), 2.74- 2.64 (m, 1H), 2.51-2. 43 (m, 1H), 2.39-2. 27 (m, 2H), 1.96-1. 86 (m, 1H), 1.41-1. 34 (m, 1H), 1.09 (t, 7.0 Hz); ESMS m/z 610 (M+H) +, 608 (M-H) + ; Anal. Calcd. For C35H32FN304S I/2H20 : C 68.44 H 5.33 N 6.84 ; found: C 68.42 H 5.50 N 6. 78.

Reference： [1]Patent: WO2003/76440,2003,A1 .Location in patent: Page/Page column 59-60

17
5-{(9aS)-3-(ethoxycarbonyl)-2-[2-(4-fluorophenyl)ethyl]-5-oxo-7,8,9,9a-tetrahydro-5H-pyrido[2,3-a]pyrrolizin-4-yl}-3-furoic acid [ No CAS ]
[ 34698-41-4 ]
ethyl (9aS)-4-{4-[(2,3-dihydro-1H-inden-1-ylamino)carbonyl]-2-furyl}-2-[2-(4-fluorophenyl)ethyl]-5-oxo-7,8,9,9a-tetrahydro-5H-pyrido[2,3-a]pyrrolizine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 14h;	D. 5-1 (9aS)-3- (ethoxycarbonyl)-2- [2- (4-fluorophenyl) ethyl]-5-oxo-7, 8,9, 9a- tetrahydro-5H-pyrido [2,3-a] pyrrolizin-4-yl}-3-furoic acid (0.100 g, 0.209 mmol) was dissolved in CH2CIz. 1-aminoindane (0.037 mL, 0.313 mmol) was added followed by EDCI (0.048 g, 0.251 mmol) and HOBt (0.034 g, 0.251 mmol). After 14 h of stirring at ambient temperature the reaction mixture was poured onto 5% HCl solution and extracted with CH2C12. The organics were washed with sat'd NaHC03, brine and then dried (Na2SO4), filtered and concentrated to a brown residue. Chromatography on silica gel using 4: 1 EtOAc: Hexanes eluted the product to provide the title compound upon concentration as a white solid (0.062 g, 0.105 mmol, 50% yield) :'H NMR (CDC13,400 MHz) 8 8.12 (s, 1H), 8.11 (d, J= 9. 5 Hz, 1H), 7.32 (m, 1H), 7.25-7. 15 (m, 5H), 6.96 (t, J= 8.6 Hz, 2H), 6. 32 (m, 1H), 5.69 (dd, J= 15.5, 7.7 Hz, 1H), 4. 65 (dd, J= 10.4, 6.2 Hz, 1H), 4.37 (dd, J= 14.2, 7.0), 3.73-3. 63 (m, 1H), 3.44-3. 38 (m, 1H), 3.17-3. 01 (m, 5H), 2.92-2. 83 (m, 1H), 2.68-2. 60 (m, 1H), 2.48-2. 40 (m, 1H), 2.37-2. 25 (m, 2H), 1.96-1. 86 (m, 1H), 1.38-1. 30 (m, 1H), 1.27 (t, J= 7. 1 Hz, 3H); ESMS m/z 594 (M+H) +, 592 (M-H) + ; Anal. Calcd. For C35H32FN305 1/2H2O : C 69.75 H 5.52 N 6.97 ; found: C 69.58 H 5.43 N 7.05.

Reference： [1]Patent: WO2003/76440,2003,A1 .Location in patent: Page/Page column 63

18
[ 769-54-0 ]
[ 34698-41-4 ]
[ 133093-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; dichloromethane; ethyl acetate;	EXAMPLE 9 N-(Indan-1-yl)-4-nitro-3-pyridinamine-1-oxide A solution of <strong>[769-54-0]3-fluoro-4-nitropyridine-1-oxide</strong> (5.6 g) and indan-1-amine (6 g) in 100 ml ethanol was stirred at reflux for one hour and thereafter cooled and concentrated to 12 g of solid. This solid was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane) to give 9.2 g solid, m.p. 137-138. An analytical sample was obtained by recrystallizing 2.7 g from ethanol to give 2.5 g crystals, m.p. 141-142.
	In ethanol; dichloromethane; ethyl acetate;	EXAMPLE 9 N-(Indan-1-yl)-4-nitro-3-pyridinamine-1-oxide A solution of <strong>[769-54-0]3-fluoro-4-nitropyridine-1-oxide</strong> (5.6 g) and indan-1-amine (6 g) in 100 ml ethanol was stirred at reflux for one hour and thereafter cooled and concentrated to 12 g of solid. This solid was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane) to give 9.2 g solid, m.p. 137-138. An analytical sample was obtained by recrystallizing 2.7 g from ethanol to give 2.5 g crystals, m.p. 141-142. ANALYSIS: Calculated for C14 H13 N3 O3: 61.98% C., 4.83% H, 15.49% N. Found: 62.11% C., 4.89% H, 15.59% N.

Reference： [1]Patent: US4970219,1990,A
[2]Patent: US4983615,1991,A

19
[ 2004-07-1 ]
[ 34698-41-4 ]
[ 96323-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; water;	EXAMPLE 3 N(6)-(1-Indanyl)-2-aminoadenosine A mixture of 2.0 g of 6-Chloro-2-aminopurine riboside, 1.1 g of 1-aminoindane and 1.0 g of triethylamine are refluxed in 50 ml ethanol under nitrogen for 20 hours. The solvent is evaporated and the residue is treated with 100 ml of cold water. The solid material thus obtained is filtered, dried, and purified by flash chromatography on silica gel. The product is eluted with 5% methanol-chloroform. Evaporation of the solvent from the pure fractions followed by crystallization from chloroform-hexane affords 1.9 g (72%) of N(6)-(1-indanyl)-2-aminoadenosine; having a melting point of 143-146 C. Anal. Calcd for C19 H22 N6 O4.0.3H2 O: C, 56.51; H, 5.64; N, 20.80 Found: C, 56.90; H, 6.06, N, 20.38.

Reference： [1]Patent: US4501735,1985,A

20
1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride [ No CAS ]
[ 34698-41-4 ]
[ 80029-43-2 ]
[ 197507-59-8 ]
[1,6]naphthyridine-2-carboxylic acid indan-1-ylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;	Compound #10 <strong>[197507-59-8][1,6]naphthyridine-2-carboxylic acid</strong> indan-1-ylamide To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (6.3 mL) at room temperature was added sequentially 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 1-aminoindan (56.0 muL, 0.431 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum and the resulting residue was re-dissolved in CH2Cl2 (50 mL). The organic layer was washed with aqueous NaHCO3, dried over anhydrous Na2SO4, and concentrated to give the crude mixture. Flash column chromatography of the crude (50% hexane/ethyl acetate to 100% ethyl acetate) afforded the desired product as a white solid (80.1 mg, 96%): m.p. 156-157 C.

Reference： [1]Patent: US6255318,2001,B1

21
[ 34698-41-4 ]
5-benzenesulfonyl-2-methyl-benzenesulfonyl chloride [ No CAS ]
N-(2,3-dihydro-1H-inden-1-yl)-2-methyl-5-(phenylsulfonyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;	Example 415: N-(2,3-dihydro-lH-inden-l-yl)-2-methyl-5- (phenylsulfonyl)benzenesulfonamide[0437] In an analogous manner to Example 294, 5-benzenesulfonyl-2-methyl- benzenesulfonyl chloride, triethylamine, and 1-aminoindane in dichloromethane were used to prepare N-(2,3-dihvdro-lH-inden-l-yl)-2-methyl-5-(phenylsulfonyDbenzenesulfonamide. MS (ESI-) m/z 426.

Reference： [1]Patent: WO2006/124875,2006,A2 .Location in patent: Page/Page column 148

22
[ 19975-56-5 ]
[ 34698-41-4 ]
[ 927403-90-5 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 1-aminoindane (0.5 ml, 3.87 mmol), 2-methylthio-2-thiazoline (0.421 ml, 3.87 mmol), and methanesulfonic acid (0.251 ml, 3.87 mmol) in butanol (5 ml) was heated under reflux at 125 C bath temperature for 16 hours. The solvent was evaporated, the crude product separated between HCl (2M) and diethyl ether. The organic phase was made basic with NaOH (32%) and the product extracted into dichloromethane, dried (MgSO4) and evaporated to yield 912 mg of product as beige crystals m.p. 137 C.

Reference： [1]Patent: WO2007/20377,2007,A2 .Location in patent: Page/Page column 149

23
[ 463-71-8 ]
[ 34698-41-4 ]
[ 71492-66-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In chloroform; water; at 20℃;	P.3 lsonicotinic acid 2-(3-indan-1-yl-thioureido)-ethyl ester (compound example 13 of table 1 ); To a solution of thiophosgene (4.14 g) in chloroform was added at RT a solution of 13.25 g potassium carbonate in 70 ml of water. To this mixture was added a solution of indanyl-1 -amine (4.00 g) in chloroform (100 ml) and the mixture stirred at RT overnight. The reaction mixture was washed with water (2 x) and the organic phase dried over sodium sulfate. Evaporation of the solvent yielded the product (5.20 g, 99%) which was used for the following step without further purification.
	With potassium carbonate; In dichloromethane; water; at 0℃; for 0.166667h;	A mixture of 2,3 ml (27,1 mmol) thiophosgene in 20 ml dichloromethane is cooled to 0 C after which a cold (0 C) solution of 3,1 g (22,5 mmol) K2CO3 in 22 ml water is added. The mixture is stirred for 10 min and 3 ml (22,5 mmol) indan-1-ylamine is then added dropwise with vigorous stirring at 0 C. After an additional 10 min a cold solution of 2,5 g KOH in 22 ml water is added in one portion with cooling. The organic layer and three extracts (Et2O) are combined, dried over MgSO4, filtered and concentrated to give 3,9 g of crude 1- isothiocyanato-indane as a brown liquid. The product is used directly without further purification.1H-NMR (ppm, CDCI3): 2,20-2,30 (m, 1H); 2,50-2,60 (m, 1 H); 2,85-2,95 (m, 1H); 3,05-3,15 (m, 1 H); 5,20 (t, 1 H); 7,20-7,35 (m, 3H); 7,40-7,50 (m, 1H).

Reference： [1]Patent: WO2007/60120,2007,A1 .Location in patent: Page/Page column 49
[2]Patent: WO2008/9881,2008,A1 .Location in patent: Page/Page column 63

24
[ 6165-75-9 ]
[ 34698-41-4 ]
[ 1875-50-9 ]

Yield	Reaction Conditions	Operation in experiment
96.6%	With sodium hydroxide; In water; toluene; at 20 - 47℃; for 4.95h;Inert atmosphere; Industry scale;Product distribution / selectivity;	Step 1-Preparation of Racemic PAI Base, 1200 Liter Lass-Lined Reactor, with PTFE Lined Piping and Under Nitrogen Atmosphere.1-Aminoindan (90 kg), toluene (180 kg), soft water (287 kg) and pure NaOH (118 kg of 25percent solution) were introduced into reactor at stirring and were mixed at ambient temperature. Then 135 kg of Propargyl Benzene Sulfonate (PBS) and 55 kg of toluene were added by portions over 45 minutes and the reaction mixture was heated 40° C. and held for 4'2 hrs at 41-47° C. After the reaction completion the stirrer was stopped and the reaction mixture was settled at this temperature for 30 minutes. Lower aqueous phase was separated and discarded to waste.Upper organic phase was mixed with 270 kg of soft water and 33percent H2SO4 solution was then added by portions. During the addition reaction temperature was maintained within the range 40-47° C. and pH of the mixture was monitored by pH-meter.After adjusting pH of reaction mixture to 2.4 (94 kg of 33percent H2SO4 solution added) the stirrer was stopped and the batch was settled for 30 minutes. The lower aqueous phase was separated using glass separation tank, organic phase was discarded to waste and the aqueous phase was re-introduced into the reactor.Toluene (155 kg) was added to the batch and then pH was adjusted to 6.1 by addition of 25percent NaOH at stirring (82 kg added) while temperature was maintained within the range 44-46° C. The stirrer was stopped and the reaction mixture was settled at this temperature for 30 minutes. Lower aqueous phase was separated using glass separation tank, organic phase was transferred to glass lined vessel (Extract I) and aqueous phase was re-introduced into the reactor.Toluene (115 kg) was added to the aqueous phase, the batch was stirred and then pH was adjusted to 6.7 by addition of 25percent NaOH (3 kg added) while temperature was maintained within the range 45-47° C. The stirrer was stopped and the reaction mixture was settled at this temperature for 30 minutes. Lower aqueous phase was separated to waste and organic phase was mixed with the organic phase from previous extraction (Extract I) held in glass lined vessel.The combined organic solution was washed with 377 liters of soft water at 41-46° C. by stirring for 11/2 hours. Then the stirrer was stopped and the mixture was settled at this temperature for 30 minutes. Lower aqueous phase was separated to waste and organic phase was evaporated under vacuum at heating and stirring.After completion of Toluene evaporation, Isopropanol (106 kg) was added to the residue and evaporated under the same conditions.The residue of evaporation (oil) was cooled to 30° C. and transferred into glass lined vessel.Product-78 kg Racemic PAI Base, Assay-96.6percent
		1-aminoindan (45 g), toluene (135 ml), water (85 ml) and NaOH (60 g of 25percent solution) were introduced into a reactor, stirred, and PBS (67.5 g) was added at ambient temperature. The reaction mass was heated to 45° C. and held at this temperature for 4 hours. The stirrer was stopped and the reaction mixture was allowed to settle. After phase separation, the lower aqueous phase was discarded. The upper organic phase was mixed with 300 ml of water and was stirred. The resulting mixture was acidified with 66percent sulfuric acid to a pH of 2.2 and stirring was stopped. The mixture was settled for 1/2 hour and the lower phase (acidic aqueous layer) was separated. The upper organic phase was discarded. The aqueous phase was mixed with 250 ml of toluene while stirring and was basified to a pH of 6.3 with a 25percent solution of NaOH. After the pH was adjusted to 6.3, the stirrer was stopped and the mixture was allowed to settle. The lower aqueous phase and the upper toluenic phase were separated. The aqueous phase was reintroduced into the reactor, mixed with an additional 200 ml of toluene. The reactor was stirred and the pH was adjusted to 7.0 with a 25percent solution of NaOH. After pH adjustment, the stirrer was stopped and the mixture was allowed to settle. The lower aqueous phase was separated and discarded. The organic toluene phase was combined with the organic toluene phase from the previous extraction and was washed with 200 ml water. After the washing and settling, the aqueous layer was separated and the resulting organic toluene phase was evaporated in rotating evaporator under vacuum. After the toluene evaporation, the residue was dissolved in 80 ml isopropanol and the solvent was evaporated under the same conditions. 38.6 g of brown oil (PAI base) resulted. Aqueous solution of L-tartaric acid was prepared by dissolution of 12.36 g of the acid in 19.6 g water. PAI base was dissolved in 225 ml isopropanol, stirred, heated to reflux and the solution of L-tartaric acid was added to the PAI solution at reflux conditions. The addition resulted in crystallization of solid rasagiline tartrate salt. The suspension was cooled to room temperature, filtered and the solid product was washed on a filter with two portions of isopropanol. The wet solid product was dried to a constant mass and was analyzed. Yield 24.0 g (28.8percent) Analysis: m.p. 176.3-176.8° C., Purity by TLC: one spot. Purity by HPLC: AI content 0.1percent; S-isomer content: <4percent; remainder R-PAI. Solid morphology: Aggregated small (100-300 micron) needle-shaped crystals.
	With sodium hydroxide; In water; toluene; at 20 - 45℃; for 4h;Product distribution / selectivity;	1-aminoindan (45 g), toluene (135 ml), water (85 ml) and NaOH (60 g of 25percent solution) were introduced into a reactor, stirred, and PBS (67.5 g) was added at ambient temperature. The reaction mass was heated to 45° C. and held at this temperature for 4 hours. The stirrer was stopped and the reaction mixture was allowed to settle. After phase separation, the lower aqueous phase was discarded. The upper organic phase was washed with 70 ml water and was evaporated under vacuum in a rotating evaporator. The residue which resulted was dissolved in 70 ml isopropanol and the solvent was again evaporated under the same conditions. The resulting brown oil (55.4 g) was dissolved in 205 ml isopropanol while being stirred in a reactor. A solution of 12.6 g L-tartaric acid in 19.7 ml water was prepared. The reactor with isopropanolic solution was heated to reflux while stirring, and the solution of L-tartaric acid was added dropwise at reflux. A solid product was precipitated during the addition of acid. The resulting suspension was cooled to 25° C., and the solid product was filtered and washed with isopropanol. The wet solid was dried under vacuum. The dry solid product (28.7 g of white crystalline powder) was sampled and analyzed. Analysis: m.p. 162.7-163.2° C., Purity by TLC: two spots. Purity by HPLC: AI content 22.6percent; S-isomer content: 12percent; remainder R-PAI.; 1-aminoindan (45 g), toluene (135 ml), water (85 ml) and NaOH (60 g of 25percent solution) were introduced into a reactor, stirred, and PBS (67.5 g) was added at ambient temperature. The reaction mass was heated to 45° C. and held at this temperature for 4 hours. The stirrer was stopped and the reaction mixture was allowed to settle. After phase separation, the lower aqueous phase was discarded. The upper organic phase was washed with 70 ml water and was evaporated under vacuum in a rotating evaporator. The residue which resulted was dissolved in 70 ml isopropanol and the solvent was again evaporated under the same conditions. The resulting brown oil (56.5 g) was dissolved in 120 ml of isopropanol while being stirred stirring in reactor. An L-tartaric acid solution was prepared by dissolving 12.6 g of L-tartaric acid in 125 ml isopropanol and heating. The solution in the reactor was heated to reflux while being stirred and then the L-tartaric acid solution was introduced to the reactor dropwise under reflux conditions. A solid product was precipitated during the addition. The resulting suspension was cooled to 25° C. and the solid product was filtered and washed with isopropanol. The wet solid dried under vacuum. 33.9 g of dry solid product in the form of white crystalline powder was sampled and analyzed. Analysis: m.p. 160.8-161.2° C., Purity by TLC-two spots (AI+PAI) Purity by HPLC-AI content 25.6percent; S-isomer content 16percent; 1-aminoindan (45 g), toluene (135 ml), water (85 ml) and NaOH (60 g of 25percent solution) were introduced into a reactor, stirred, and PBS (67.5 g) was added at ambient temperature. The reaction mass was heated to 45° C. and held at this temperature for 4 hours. The stirrer was stopped and the reaction mixture was allowed to settle. After phase separation, the lower aqueous phase was discarded. The upper organic phase was washed with 70 ml water and was evaporated under vacuum in a rotating evaporator. The residue which resulted was dissolved in 70 ml isopropanol and the solvent was again evaporated under the same conditions. The resulting brown oil (56.5 g) was dissolved in 120 ml isopropanol while stirring in reactor. 8.2 g of L-tartaric acid was dissolved in 19 ml water. The solution in the reactor was heated to reflux while stirring and the solution of tartaric acid was introduced to the reactor dropwise under reflux conditions. Solid product was not precipitated during the addition. The resulting mixture was cooled and seeded with rasagiline tartrate at 73° C. The seeding material was not dissolved and at 64° C. crystallization of the batch was observed. The batch was cooled to 25° C. over 12 hours and stirred at this temperature for 6 hours. The solid product was filtered and washed with isopropanol. The wet solid was dried under vacuum. 20.6 g of dry solid product in the form of white crystalline powder was sampled and analyzed. Analysis: m.p. 162.9-163.2° C., Purity by TLC-two spots (AI+PAI) Purity by HPLC-AI content 39.8percent, PAI content 62.2percent; S-isomer content: much greater than 4percent. (Note: It was difficult to determine the exact content of S-enantiomer because the broad peak of AI overlapped the peak of the S-enantiomer). Discussion: Examples 3, 4 and 5 show that it is difficult to directly separate pure mono-propargylated aminoindan derivative from the reaction mixture. The crude salts produced upon the addition of L-tartaric acid to the reaction mixture are contaminated by primary aminoindan as well as by S-enantiomer.; 1-aminoindan (45 g), toluene (135 ml), water (85 ml) and NaOH (60 g...

Reference： [1]Patent: US2011/152381,2011,A1 .Location in patent: Page/Page column 8-9
[2]Patent: US2007/112217,2007,A1 .Location in patent: Page/Page column 8
[3]Patent: US2007/112217,2007,A1 .Location in patent: Page/Page column 9-11

25
[ 873-83-6 ]
[ 34698-41-4 ]
6-aminoindan hydrochloride [ No CAS ]
6-(indan-1-ylamino)-1H-pyrimidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.8%	In ethanol; at 140 - 160℃; for 5h;	<strong>[34698-41-4]1-Aminoindan</strong> hydrochloride (11.07 g, 0.069 mol) and 6- aminouracil (9.32 g, 0.073 mol) were mixed mechanically with 1-aminoindan (10.39 g, 0.78 mol) and heated to 16O0C for 5 h. The liquid mixture was allowed to cool to 14O0C. While stirring vigorously and heating, ethanol (130 ml) was cautiously added through the condenser, thus obtaining a smooth thick suspension which was cooled and filtered. All remaining hard material was crushed. The solid was washed with ethanol and stirred vigorously in 2N NaOH (70 ml) . After ca 3 minutes the suspension was filtered, washed with a little 2N NaOH and finally water. The solid was dried in vacuo at 600C overnight ; 'crys'tallizealpha by dissolution in acetic acid (125 ml) , treatment with charcoal, and after hot filtration, treatment at reflux with water (40 ml) . After cooling, the solid was collected, washed with dilute acetic acid, ethanol and ether and dried in vacuo for 8 h (11.39 g, 63.8%). A sample was recrystallized as follows: It was taken up (4.9 g) in refluxing acetic acid (60 ml) , filtered hot through hiflo and the refluxing mixture treated with water (35 ml) . The solid obtained on gradual cooling was collected, washed and dried at 6O0C in vacuo (3.95 g) , mp 271C. Ci3H13N3O2 requires: C, 64.19; H, 5.39; N, 17.27%. Found: C, 63.92; H, 5.58; N, 17.57 %. MS (CI/NH3): 244 (MH+, 100%) . 1H MMR (DMSO-d6) delta ppm: 10.25 (br s, N3-H) ; 9.68 (br s, Nl- H), 7.3 (m, 4H, Ar-H4); 6.44 (d, J=7.5 Hz, H, IndNH) ; 4.94 (q, J=7.2 Hz, H, Cl'-H); 4.66 (d, J=I.5 Hz, H, C5-H) ; 2.89-3.02 (m, H, C3'-H); 2.75-2.89 (m, H, C3'-H); 2.44-2.57 (m, H, C2'- H); 1.74-1.91 (m, H, C2'-H) . IR: 3231, 1717, 1610 br, 1380, 763, 545 cm"1.

Reference： [1]Patent: WO2006/20070,2006,A2 .Location in patent: Page/Page column 57; 59

26
[ 1206880-04-7 ]
[ 34698-41-4 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 392 - 395

27
[ 34698-41-4 ]
[ 68253-35-0 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 2079 - 2081
[2]Journal of Organic Chemistry,2013,vol. 78,p. 2301 - 2310

28
[ 17640-21-0 ]
[ 34698-41-4 ]
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide [ No CAS ]
[ 10277-74-4 ]

Yield	Reaction Conditions	Operation in experiment
44%; 39%	With Novozym 435; at 23℃; for 2h;Molecular sieve; Enzymatic reaction;	General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 230 - 236
[2]Synthesis,2008,p. 2283 - 2287

29
[ 34698-41-4 ]
[ 106-95-6 ]
[ 91639-43-9 ]

Yield	Reaction Conditions	Operation in experiment
		l-aminoindan (loogm) was stirred in 1000 ml of acetonitrile 100 gm of potassium carbonate was added and was stirred at 600C to 700C. Allyl bromide (60 gm) was added slowly to the reaction mass at 60-70 0C. The reaction mass was refluxed for about 12-13 hrs. The reaction mass was then quenched in 2.5 lit of water and later extracted with 500 ml of ethyl acetate. The organic phase was dried over sodium sulphate. 125 gm of oxalic acid was added to the ethyl acetate layer at 25-300C. The resulting precipitate was at 25-300C for 2 hrs & filtered. The solid was recrystalized from methanol to yield 100 gm of the N-allyl-i-aminoindan oxalate.

Reference： [1]Patent: WO2009/81148,2009,A1 .Location in patent: Page/Page column 11
[2]Asian Journal of Chemistry,2017,vol. 29,p. 1357 - 1359

30
[ 542-75-6 ]
[ 34698-41-4 ]
N-2-propene-1-yl-3-chloro-trans-aminoindan hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		A 250 ml round bottom flask equipped with a mechanical stirrer and nitrogen inlet was charged with (R)-AI (10 g, 75 mmol), K2CO3 (10.36 g, 75 mmol) and 26 ml N,N-dimethylacetamide. The reaction mixture was heated to 60 C. and 1,3-dichloropropene (8.35 ml, 0.8 eq., Aldrich 40, 373-3, tech., 80%, mixture of isomers) in toluene (9 ml) were added dropwise within 10 min. After another 4.5 hr of stirring the reaction mixture was cooled and 60 ml water and 30 ml toluene were added. The aqueous phase was separated and extracted again with 30 ml toluene. The combined toluene extracts were washed with 50 ml water, then 50 ml water were added and the pH was adjusted to 2.5 with 6NH2SO4. The water phase was separated, 50 ml toluene was added and the pH was adjusted to 6.5. The organic phase was separated, the water phase was extracted with another portion of toluene (30 ml), the toluene extracts were combined and evaporated to give 12.2 g (78%) crude products. TLC (hexane-4/EA-6) showed 2 main products: trans-3-chloro-AAI, RF=0.47; cis-3-chloro-AAI, RF=0.33 (see scheme 1). 2. The separation of trans-3-chloro-AAI from the 12.2 g crude cis/trans mixture was done by filtering-column chromatography over 400 g silica (Merck type 9385) with an eluent composed of EA/hexane (3/7). The yield of pure trans-3-chloro-AAI was 4.5 g (29% overall yield of steps 1 and 2). 3. To 4.5 g of trans-3-chloro-AAI base (from step 2) in 80 ml diethyl ether was added 14.5% HCl/ethanol solution. The reaction mixture was stirred for ½ hr at ambient temperature and ½ hr at 5-10 C. The precipitate was filtered, washed with ether and dried in vacuum at 50 C. to give 4.9 g (94% yield) of the pure compound, m.p.=192-195 C. (see scheme 1). The compound exhibited satisfactory NMR and MS spectra which confirmed its structure. NMR peak assignments are listed below Proton delta (ppm) Multiplicity H1 (1H) 4.75 dd H2a (1H) 2.24 m H2b (1H) 2.40 m H3I (1H) 2.86 ddd H3II (1H) 3.18 dt H5, H6, H7 (3H) 7.24-7.35 m H8 (1H) 7.81 d H10 (2H) 3.76, 3.78 m H11 (1H) 6.70 dt H12 (1H) 6.30 dd H13 (2H) 10.10 broad s

Reference： [1]Patent: US7572834,2009,B1 .Location in patent: Page/Page column 15-16

31
[ 34698-41-4 ]
[ 14246-53-8 ]
[ 1190868-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3-Dicyclohexylurea In chloroform at 65℃; for 15h;

Reference： [1]Nechab, Malek; El Blidi, Lahssen; Vanthuyne, Nicolas; Gastaldi, Stephane; Bertrand, Michele P.; Gil, Gerard [Organic and Biomolecular Chemistry, 2008, vol. 6, # 21, p. 3917 - 3920]

32
[ 34698-41-4 ]
[ 201870-90-8 ]
[ 943925-99-3 ]

Yield	Reaction Conditions	Operation in experiment
73%		Synthesis Example 15; Tert-Butyl (S)-1-(2,3-dihydro-1H-inden-1-ylcarbamoyl)-3-(trifluoromethylthio) propylcarbamate (Starting Material for sk-276) N-Boc-trifluoromethionine (200 mg, 0.659 mmol) was dissolved in 6.6 ml of dry THF in the presence of N2, and the temperature was adjusted to -78 C. Subsequently, N-methylmorpholine (0.09 ml, 0.794 mmol) was added thereto, and the mixture was stirred. Two minutes later, isobutyl chloroformate (0.10 ml, 0.794 mmol) was added thereto, and the mixture was stirred for 2 minutes. Finally, 1-aminoindane (0.10 ml, 0.794 mmol) was added thereto. TLC was performed to confirm disappearance of the starting compound, and the solid matters were filtered, followed by distillation of THF under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate=90/10 then 80/20), thereby the product (200.4 mg, 73%) was obtained.1H-NMR (CDCl3, 200 MHz) delta1.41 (s, 9H), 1.73-1.84 (m, 1H), 2.04 (m, 1H), 2.25 (m, 1H), 2.55 (m, 1H), 2.97 (m, 4H), 4.24 (q, 1H, J=6.6 Hz), 5.17 (s, 1H), 5.42 (q, 1H, J=7.8 Hz), 7.21 (m, 4H)19F-NMR (CDCl3, 188 MHz) delta: -41.3 (s)

Reference： [1]Patent: US2010/76224,2010,A1 .Location in patent: Page/Page column 8

33
[ 10277-74-4 ]
[ 34698-41-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 2h;Inert atmosphere;	0.1 g of (5)-l-aminoindan was dissolved in 0.1 ml of dry dimethylsulfoxide and 0.01 g of potassium tert.butoxide was added. The reaction mixture was heated in argon atmosphere for 2 hours at 120C. After cooling, the mixture was diluted with 0.5 ml of 15% aqueous NaOH and extracted with 2 x 0.5 ml of dichloromethane. The organic fraction was filtered with activated carbon, washed with 2 ml of ethanol and concentrated to dryness. The yield was 0.094 g (94% of the theoretical value), the chemical purity was 96% (HPLC), and the optical purity was 1.2 % ee (HPLC).

Reference： [1]Patent: WO2012/116752,2012,A1 .Location in patent: Page/Page column 13
[2]Chemistry - A European Journal,2009,vol. 15,p. 12780 - 12790
[3]Organic Process Research and Development,2014,vol. 18,p. 1169 - 1174

34
[ 5600-21-5 ]
[ 34698-41-4 ]
[ 1233390-71-0 ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium carbonate; In N,N-dimethyl-formamide; at 145℃; for 3h;	A mixture of 2.9 g (20 mmol) of 2-amino-4-chloro-6-methylpyrimidine, 2.9 g (22 mmol) of 1-aminoindane and 4.1 g (30 mmol) of potassium carbonate in 30 ml of dimethylformamide is heated at 145 C. for 3 hours. After cooling, the reaction mixture is hydrolyzed, the aqueous mixture is extracted with methylene chloride, the separated-off organic phase is dried with sodium sulfate. After filtering off the drying agent and concentrating the organic phase by evaporation, the crude mixture is separated by means of column chromatographic separation using ethyl acetate/methanol/triethylamine 90/10/1 as eluent. The 2-amino-4-indanyl-1-amino-6-methylpyrimidine obtained in this way is taken up in ethyl acetate/heptane 2:8 and treated with activated carbon. After separating off the activated carbon and concentrating the solvent by evaporation, 1 g of 2-amino-4-indanyl-1-amino-6-methylpyrimidine is obtained (glass-like solid, m.p: 53-54 C., 20% yield, 95% purity).

Reference： [1]Patent: US2010/167935,2010,A1 .Location in patent: Page/Page column 24

35
[ 83-33-0 ]
[ 34698-41-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	With ammonium formate; zinc; In methanol; for 5h;Reflux;	The corresponding ketone (10 mmol: 1.14 g of 1a, 0.98 g of 1b, 1.48 g of 1c, 1.46 g of1d, 1.46 g of 1e, 1.32 g of 1f, 1.20 g of 1g, 1.70 g of 1h, 1.70 g of 1i), ammonium formate (60 mmol, 3.78g) and Zn powder (30 mmol, 1.96 g) in methanol (30 mL) was stirred under reflux. After completion of thereaction the mixture was filtered through Celite and the solvent was removed by vacuum rotaryevaporation. The residue was treated with conc. HCl solution (4 mL) and water (30 mL), and then extractedwith diethyl ether (2x20 mL) to remove organic residues. The aqueous phase was alkalized with ammoniasolution to pH=10 and extracted with dichloromethane (4x25 mL). The organic phase was washed withbrine, dried over sodium sulphate and the solvent removed under vacuum.
56%	With ammonium formate; zinc; In methanol; for 5h;Inert atmosphere; Reflux;	To a stirred solution of 1-indanone (8) (5 g, 0.0379 mol, 1.0 eq), ammonium formate (14.31 g, 0.227 mol, 6.0 eq) and Zn powder (6.9 g, 0.113 mol, 3.0 eq) in methanol (100 mL) was stirred under reflux. After completion of the reaction the mixture was filtered through celite and the solvent was removed by vacuum. The residue was treated with conc. HCl solution (4 mL) and water (30 mL) and then extracted with EtOAc (2 x 50 mL) to remove organic residues. The aqueous phase was alkalized with ammonia solution to and extracted with EtOAc (4 x 40 mL). The organic phase was washed with brine, dried over sodium sulphate and the solvent removed under vacuum resulted compound 3 2.75 g as 56 % yield (80.18 % by HPLC). 1H NMR (400 MHz, CDCl3); delta 7.72 (d, 1H, Ar-H), 7.24 (m, 3H, Ar-H), 5.82 (d, 1H, NH), 5.58 (d, 1H, NH), 4.90 (t, 1H, CH-NH2), 3.79 (d, 1H, Ar-CH2), 3.65 (d, 1H, Ar-CH2), 3.17 (m, 1H, CH2-CH), 2.89 (m, 1H, CH2-CH).Mass: m/z calcd. 133.09, found m/z 117.0 (M-NH2)+.

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 245 - 252
[2]Chemical Science,2020,vol. 11,p. 2973 - 2981
[3]Science,2017,vol. 358,p. 326 - 332
[4]Journal of Organic Chemistry,2019,vol. 84,p. 10962 - 10977
[5]Tetrahedron Letters,2011,vol. 52,p. 1310 - 1312
[6]Asian Journal of Chemistry,2017,vol. 29,p. 1357 - 1359
[7]Advanced Synthesis and Catalysis,2016,vol. 358,p. 358 - 363
[8]Chirality,2018,vol. 30,p. 900 - 906
[9]Green Chemistry,2017,vol. 19,p. 1134 - 1143
[10]Journal of Organic Chemistry,2010,vol. 75,p. 5265 - 5270
[11]Patent: WO2012/153349,2012,A2
[12]Organic Process Research and Development,2014,vol. 18,p. 1169 - 1174
[13]Patent: WO2015/70995,2015,A1
[14]Patent: WO2016/116607,2016,A1
[15]Journal of Organic Chemistry,2019,vol. 84,p. 4856 - 4866
[16]Angewandte Chemie - International Edition,2020,vol. 59,p. 3900 - 3904
Angew. Chem.,2020,vol. 132,p. 3928 - 3932,5

36
[ 34698-41-4 ]
[ 33263-43-3 ]
C₁₄H₁₅N₃O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2040 - 2043

37
[ 34698-41-4 ]
[ 33263-43-3 ]
[ 1297487-89-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2040 - 2043

38
[ 34698-41-4 ]
[ 161735-79-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 24 h / 55 °C 2.1: isopropyl alcohol / 1.5 h / 25 - 30 °C / Reflux 3.1: ammonia / water / pH ~ 8.5 - 9 3.2: 2 h / 25 - 30 °C
	Multi-step reaction with 4 steps 1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 2: 0.75 h / 25 - 65 °C 3: sodium hydroxide / water / 20 °C 4: acetone / 1 h / 25 - 35 °C
	Multi-step reaction with 5 steps 1.1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 2.1: 0.75 h / 25 - 65 °C 3.1: sodium hydroxide / water / 20 °C 4.1: hydrogen bromide / 0.5 h / 25 - 65 °C 5.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 5.2: 0.5 h / 40 °C

	Multi-step reaction with 4 steps 1: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 2: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 3: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux 4: isopropyl alcohol / 0.5 h / 5 - 10 °C
	Multi-step reaction with 6 steps 1: ethanol; tert-butyl methyl ether / 20 °C 2: ethanol / 2.32 h / 79 °C 3: sodium hydroxide / ethyl acetate / 0.5 h / 20 °C 4: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 5: sodium hydroxide / toluene / 29 h / 30 °C 6: isopropyl alcohol / 1 h / 55 - 80 °C

Reference： [1]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - WO2011/48612, 2011, A2
[2]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2012/153349, 2012, A2
[3]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2012/153349, 2012, A2
[4]Ma, Guozhen; Xu, Zhongqi; Zhang, Pengfei; Liu, Jinpo; Hao, Xilin; Ouyang, Jingping; Liang, Ping; You, Song; Jia, Xian [Organic Process Research and Development, 2014, vol. 18, # 10, p. 1169 - 1174]
[5]Current Patent Assignee: KRKA DD NOVO MESTO - WO2015/70995, 2015, A1

39
[ 34698-41-4 ]
[ 624-65-7 ]
[ 1875-50-9 ]
[ 92850-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 55℃; for 24h;	COMPARATIVE EXA MPLE: PREPARATION OF RACEMIC RASAGILINE prepared as in United States Patent 5 ,532.41 51 -Aminoindane ( 1 00 g, 0.75mol), propargyl chloride (56 g, 0.75mol), potassjum carbonate ( 104 g. 0.75 mol) and acetonitrile (800) were charged in a clean and dry 4 neck round bottom flask and the reaction mixture was stirred at about 55°C for about 24 hrs. Thereafter, reaction mass was cooled to about 25°C, filtered, and the residue was washed with acetonitri le (200 ml). The resultant filtrate was concentrated under reduced pressure at about 40°C to obtain I 30 grams of the racemic rasagiline base as an oily residue.Purity by HPLC : Rasagil ine base: 72.33 %, Unreacted 1 -aminoindane: 14.97%,

Reference： [1]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - WO2011/48612, 2011, A2 Location in patent: Page/Page column 22

40
[ 34698-41-4 ]
[ 136236-51-6 ]

Reference： [1]Patent: US2011/152381,2011,A1
[2]Patent: WO2012/153349,2012,A2
[3]Organic Process Research and Development,2014,vol. 18,p. 1169 - 1174
[4]Patent: WO2015/70995,2015,A1

41
[ 97-67-6 ]
[ 34698-41-4 ]
(R)-1-aminoindan hydrogen-L-(-)-malate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In methanol; at 50℃;Resolution of racemate;	lg of racemic 1-aminoindan was dissolved in 5 ml of methanol. 1.06 g of L(-)-malic acid was dissolved in 5 ml of methanol. The solution of 1-aminoindan was heated to 50C and the solution of malic acid was added under stirring. The reaction mixture was cooled to 35C, seeded and the formed suspension was held at 35C for 1 hour. Then the mixture was cooled during 2 hours to 20C and held at this temperature for 3 hours. The precipitate was filtered, washed with 2 ml of methanol and dried to obtain 0.473 g of (R)- 1-aminoindan hydrogen-L-(-)-malate (47% of the theoretical value). The optical purity was 99.75% (HPLC).

Reference： [1]Patent: WO2012/116752,2012,A1 .Location in patent: Page/Page column 12

42
[ 34698-41-4 ]
[ 624-65-7 ]
[ 1875-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide at 40 - 70℃; for 7h;	8.C C) Preparation of racemic rasagiline free baseDimethyl formamide 600 mL, 100 g of racemic 1-aminoindane, 124.2 g of potassium carbonate and 9 g sodium hydroxide were taken in round bottom flask and heated to get 40°C. 67 g of propargyl chloride was added gradually while maintaining the temperature at 40°C. The reaction mixture was heated at 65°C to 70°C stirred for 7 hours. After completion of the reaction on TLC, the reaction mixture was cooled to 25°C and acidified with 15% HC1 solution to adjust the pH 4. The separated aqueous layer was basified with 20% NaOH solution to adjust the pH 9-10. The reaction mixture was extracted with ethyl acetate 400 mL. The ethyl acetate layer was distilled under vacuum at 55°C to obtain racemic Rasagiline base as residue as yellow oil.
	With potassium carbonate In butan-1-ol at 55 - 60℃; for 6h;

Reference： [1]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - WO2012/153349, 2012, A2 Location in patent: Page/Page column 30
[2]Easwaramoorthi; Rajendran, A. Jeya; Rao, K. Chennakesava; Arun; Balachandran; Perumal; Emi, Nobuhiko; Mahalingam; Duraipandiyan; Al-Dhabi [RSC Advances, 2015, vol. 5, # 127, p. 105266 - 105278]

43
[ 1189-71-5 ]
[ 34698-41-4 ]
[ 100-51-6 ]
[ 1426537-94-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine; In dichloromethane; at 0 - 20℃; for 4h;	General procedure: Benzylalcohol (0.65 g, 6.01 mmol) was added to a solution of CSI (0.61 g, 4.30 mmol) in CH2Cl2 (10 mL) at 0 C. A solution of amine 4 (0.83 g, 4.30 mmol) in CH2Cl2 (30 mL) and NEt3 (0.48 g, 4.72 mmol) were added to the solution of CSI drop wise and stirred at 0 C for 1 h. then at room temp for 3 h. The reaction mixture was cooled to 0 C and to this mixture was added a solution of 0.1 N HCl (50 mL). Organic phase was separated and H2O phase was extracted with CH2Cl2 (2 x 30 mL). Combined organic layers were dried over Na2SO4 and the solvent was evaporated. Column chromatography of the residue on silica gel (30 g) with 30% EtOAc/hexane yielded carbamate 10 (2.52 g, 59%) as white solid. Sulfamoylcarbamates 11-15 were also synthesized by this procedure with yields of 58%, 64%, 59%, 57% and 58%, respectively.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1379 - 1385

44
[ 34698-41-4 ]
[ 1432752-24-3 ]
[ 1432749-73-9 ]

Yield	Reaction Conditions	Operation in experiment
49%		135.3 2-(1-Ethyl-propyl)-6,7-dimethoxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid indan-1-ylamide A solution of 2-(1-ethyl-propyl)-6,7-dimethoxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid obtained in step 135.2 (300 mg, 0.939 mmol) in SOCl2 (5 mL) was stirred at 76 C. for 2 h. SOCl2 was removed. The obtained residue was dissolved in DCM (5 mL), <strong>[34698-41-4]2,3-dihydro-1H-inden-1-amine</strong> (188 mg, 1.409 mmol) was added dropwise and the resulting reaction was stirred at RT for 3 h. The solvent was removed and the obtained residue was washed with EtOAc to give the title compound (200 mg, 49%) as a yellow solid. LCMS (ESI+): m/z 435 (M+H)+, RT: 2.084 min 1H-NMR (400 MHz, MeOD): delta 7.61 (s, 1H), 7.49 (s, 1H), 7.43 (m, 1H), 7.28-7.22 (m, 3H), 5.67 (t, J=7.6 Hz, 1H), 3.95 (s, 3H), 3.94 (s, 3H), 3.09-3.05 (m, 1H), 2.97-2.91 (m, 1H), 2.65-2.60 (m, 1H), 2.08-2.01 (m, 1H), 1.88-1.77 (m, 4H), 1.29 (m, 1H), 0.84 (t, J=1.6 Hz, 6H).

Reference： [1]Patent: US2013/116229,2013,A1 .Location in patent: Paragraph 1007; 1008; 1009

45
[ 34698-41-4 ]
[ 113-24-6 ]
[ 338-69-2 ]
(S)-1-Aminoindane [ No CAS ]
[ 10277-74-4 ]
[ 83-33-0 ]

Yield	Reaction Conditions	Operation in experiment
80 % ee	With pyridoxal 5'-phosphate In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 24h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	2.4 Kinetic resolution of rac-1a-d General procedure: All experiments were carried out keeping the protein content constant (8 mg mL-1) if not otherwise stated. One of the substrates rac-1a-d (50 mM), sodium pyruvate (50 mM) and pyridoxal-5′-phosphate monohydrate (0.2 mg mL-1) in phosphate buffer (1 mL, 0.1 M, pH 7.5) containing IPA or DMSO as a possible cosolvent (10, v/v-%) was added to a 2 mL Eppendorf tube, containing the ω-transaminase sol-gel catalyst (25 or 50 mg). The reaction was shaken (170 rpm) at 30 °C. After 24 h the reaction was stopped by centrifuging the mixture and removing the solution by pipette. The solid catalyst was reused while conversion was monitored by taking a sample (5 μL) from the solution and diluting it with the HPLC eluent (500 μL). The sample was filtered and analyzed for conversion by HPLC. A sample (400 μL) for ee(S)-1 analysis was taken, and aqueous NaOH (2 M, 50 μL) was added followed by the extraction of the amine into ethyl acetate (400 μL). The organic phase (300 μL) was dried with Na2SO4, and after filtration the amine in the sample (200 μL) was derivatized with acetic anhydride (10 μL) to determine the enantiomeric excess of (S)-1 by GC.
18 % ee	With cell free extract of ω-transaminase from Sinirhodobacter hungdaonensis; PLP In aq. phosphate buffer at 30℃; for 20h; Enzymatic reaction; enantioselective reaction;

Reference： [1]Päiviö, Mari; Kanerva, Liisa T. [Process Biochemistry, 2013, vol. 48, # 10, p. 1488 - 1494]
[2]Li, Jianjiong; Wang, Yingang; Wu, Qiaqing; Yao, Peiyuan; Yu, Shanshan; Zhu, Dunming [Organic Process Research and Development, 2021]

46
[ 34698-41-4 ]
[ 113-24-6 ]
[ 338-69-2 ]
(S)-1-Aminoindane [ No CAS ]
[ 83-33-0 ]

Yield	Reaction Conditions	Operation in experiment
> 99 % ee	With pyridoxal 5'-phosphate In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 24h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	2.4 Kinetic resolution of rac-1a-d General procedure: All experiments were carried out keeping the protein content constant (8 mg mL-1) if not otherwise stated. One of the substrates rac-1a-d (50 mM), sodium pyruvate (50 mM) and pyridoxal-5′-phosphate monohydrate (0.2 mg mL-1) in phosphate buffer (1 mL, 0.1 M, pH 7.5) containing IPA or DMSO as a possible cosolvent (10, v/v-%) was added to a 2 mL Eppendorf tube, containing the ω-transaminase sol-gel catalyst (25 or 50 mg). The reaction was shaken (170 rpm) at 30 °C. After 24 h the reaction was stopped by centrifuging the mixture and removing the solution by pipette. The solid catalyst was reused while conversion was monitored by taking a sample (5 μL) from the solution and diluting it with the HPLC eluent (500 μL). The sample was filtered and analyzed for conversion by HPLC. A sample (400 μL) for ee(S)-1 analysis was taken, and aqueous NaOH (2 M, 50 μL) was added followed by the extraction of the amine into ethyl acetate (400 μL). The organic phase (300 μL) was dried with Na2SO4, and after filtration the amine in the sample (200 μL) was derivatized with acetic anhydride (10 μL) to determine the enantiomeric excess of (S)-1 by GC.

Reference： [1]Päiviö, Mari; Kanerva, Liisa T. [Process Biochemistry, 2013, vol. 48, # 10, p. 1488 - 1494]

47
[ 1188-37-0 ]
[ 34698-41-4 ]
(R)-1-aminoindan (S)-N-acetyl-L-glutaminate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; tert-butyl methyl ether; at 20℃;	Example 3b 10 g of (R, S) -1-aminoindan, 10 ml of ethanol and 40 ml of TBME were added to a reactor . To this mixture 14.2 g of <strong>[1188-37-0]N-acetyl-L-glutamic acid</strong> were added under stirring at room temperature . The ratio of (R, S) -1-aminoindan and <strong>[1188-37-0]N-acetyl-L-glutamic acid</strong> was 1:1. After a few minutes , the product started to crystallize from the solution and a thick suspension was formed to which 20 ml of TBME were added to obtain a miscible suspension, which was further stirred for 30 minutes at room temperature . After that the suspens ion was cooled to the final crystallization temperature of 5 C and left at this temperature under stirring for 2 hours . The product was filtered off us ing vacuum filtration and washed with 10 ml of TBME . Weight : 25.3 g Molar yield: 73 % Chromatographic purity: 96.1 area % Enantiomeric purity: 50.0 area % Content: 70.0 %Example 4 Optical resolution to obtain (R) -1-aminoindan N-acetyl-L- glutaminate In a reactor 70 g of (R, S) -1-aminoindan N-acetyl-L-glutaminate and 2100 ml of ethanol were added . Over the next 45 minutes the crystallization mixture was heated under stirring to a temperature of 79 C . After reaching 79 C, the mixture was stirred at this temperature for 5 minutes , then the mixture was cooled within 45 minutes to a temperature of 40 C . At this temperature the mixture was seeded with 0.7 g of crystalline (R) -1-aminoindan N-acetyl-L- glutaminate . The mixture was stirred at this temperature for 20 minutes , and then the suspens ion was cooled within 30 minutes to the final crystallization temperature of 5 C and left at this temperature under stirring overnight . The product was isolated using vacuum filtration and washed with 30 ml of cold ethanol . Weight : 29.9g Molar yield: 42.6% Chromatographic purity : 99.97% area Enantiomeric purity : 92.3"5 area

Reference： [1]Patent: WO2015/70995,2015,A1 .Location in patent: Page/Page column 18-19

48
[ 34698-41-4 ]
[ 6287-38-3 ]
(3,4-dichlorobenzyl)indan-1-yl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.2%		After 1 g (5.714 mmol) of 3,4-dichlorobenzaldehyde was dissolved in 10 mL of methanol, 0.761 g (5.714 mmol) of 1-aminoindan was added thereto and reacted at room temperature for 1 hour. 0.32 g (8.45 mmol) of sodium borohydride was slowly added thereto and stirred for 1 hour. The degree of progress of reaction was confirmed by TLC. When the reaction did not proceed further, 40 mL of water was added to the mixture, and the mixture was extracted twice with 30 mL of methylene chloride. The extracts were combined, dried with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. The resulting reaction product was separated using a silica gel-filled column with a mixed solvent of ethyl acetate and n-hexane as a mobile phase, to thereby obtain a white liquid of (3,4-dichloro-benzyl)-indan-1-yl-amine. Yield: 61.2% 1H NMR (300 MHz, CDCl3) delta 7.52 (d, J=1.8 Hz, 1H), delta 7.39 (m, 2H), delta 7.25 (m, 4H), delta 4.28 (t, J=6.5 Hz, 1H), delta 3.91 (m, 2H), delta 3.00 (m, 1H), delta 2.87 (m, 1H), delta 2.46 (m, 1H), delta 1.87 (m, 1H) .

Reference： [1]Biotechnology and Bioprocess Engineering,2016,vol. 21,p. 463 - 476
[2]Patent: US2018/271091,2018,A1 .Location in patent: Paragraph 0213-0215

49
[ 34698-41-4 ]
[ 16523-31-2 ]
(6Z)-4-(1-indanamino)-6-(1-indaniminio)-3-oxocyclohexa-1,4-dien-1-olate [ No CAS ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 5782 - 5796

50
[ 10277-74-4 ]
[ 83-33-0 ]
[ 34698-41-4 ]

Yield	Reaction Conditions	Operation in experiment
		6.53 g of ( S ) -1-aminoindane , 30 mL of toluene, 5 g of 1-indanone and 10.46 mL of triethylamine were charged into the reactor equipped with Dean-Stark apparatus . The reaction mixture was heated to reflux (T of 110C to 115C) and stirred at this temperature for 6 hours. During the reaction the conversion rate was monitored by means of HPLC. After the conversion was completed the reaction mixture was cooled to room temperature and 2.67 g of potassium t- butoxide was added to the reaction mixture. The reaction mixture was heated to reflux and stirred for 12 hours. After that the reaction mixture was cooled to room temperature, filtered and washed with 5 mL of methylene chloride. The solid was discarded; the filtrate was used in the process of hydrogenation which is in line with the process disclosed in Example 2. The final product of the reaction is racemic 1-aminoindane .

Reference： [1]Patent: WO2016/116607,2016,A1 .Location in patent: Page/Page column 26-27

51
[ 1188-37-0 ]
[ 34698-41-4 ]
(R)-1-aminoindane N-acetyl-L-glutaminate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; tert-butyl methyl ether; at 5 - 20℃;	42.9 g of (R, S) -1-aminoindane, 42.9 mL of ethanol and 174 mL of TBME were added to the reactor . To this mixture 42.6 g of N-acetyl- L-glutamic acid was added under stirring at room temperature . The ratio of (R, S) -1-aminoindane and <strong>[1188-37-0]N-acetyl-L-glutamic acid</strong> was 1/0.7. After a few minutes , the product started to crystallize from the solution and a thick suspension was formed, to which 87 mL of TBME were added to obtain a miscible suspension, which was further stirred for 30 minutes at room temperature . After that the suspension was cooled to the final crystallization temperature of 5 C and left at this temperature under stirring for 2 hours . The product was filtered off using vacuum filtration and washed with 43 mL of TBME . Weight = 89.5 g Molar yield = 68 % Chromatographic purity = 96.5 area % Enantiomeric purity = 50.03 area % Content = 78.8 %

Reference： [1]Patent: WO2016/116607,2016,A1 .Location in patent: Page/Page column 23-25

52
[ 85-46-1 ]
[ 34698-41-4 ]
N-(2,3-dihydro-1H-inden-1-yl)-1-naphthalenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With pyridine; at 0℃; for 2h;Inert atmosphere;	General procedure: To an ice-cooled solution of the amine (20mmol) in pyridine (8mL) was slowly added the corresponding sulfonyl chloride (30mmol) in pyridine (6mL). The mixture was stirred at 0C for 2h and allowed to reach room temperature. Water was added (100mL) and the solid was collected and recrystallized from MeOH:CH2Cl2.

Reference： [1]Biochemical Pharmacology,2016,vol. 115,p. 28 - 42

53
2-(2,3-dihydro-1H-inden-1-yl)isoindoline-1,3-dione [ No CAS ]
[ 34698-41-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With hydrazine hydrate; In ethanol; dichloromethane; at 80℃; for 24h;	Phthalimide 30 (110 mg, 0.42 mmol), ethanol (1.7 mL), and dichloromethane (0.57 mL) were added to a culture tube, capped with a Teflon-lined screw cap, and heated to 40 C. After the mixture became homogenous, hydrazine hydrate (82 muL, 1.7 mmol) was added, the Teflon-lined screw cap was replaced, and the mixture was heated at 80 C with stirring. After 24 h, the mixture was cooled to rt, filtered through Celite [ethanol:dichloromethane (3:1) eluent], and acidified with 3 M aq HCl. The organic phase was removed and the organic impurities were removed by washing the aqueous phase with EtOAc (3×). The resulting aqueous mixture was basified to pH?10 with 1 M aq NaOH and extracted with dichloromethane (3×). The dichloromethane extracts were combined, dried (MgSO4), and concentrated to give 31 (37 mg, 0.28 mmol, 67%). 1H NMR (300 MHz, CDCl3): delta 7.09-7.42 (m, 4H), 4.37 (dd, J=7.4, 7.5Hz, 1H), 2.97 (ddd, J=3.5, 8.7, 15.9Hz, 1H), 2.81 (ddd, J=8.2, 8.2, 16.4Hz, 1H), 2.51 (dddd, J=3.5, 7.5, 7.5, 12.4Hz, 1H), 2.1 (br s, NH2), and 1.69 (dddd, J=8.3, 8.3, 8.3, 12.5, 1H). The 1H NMR data is in good agreement with previously reported characterization results.

Reference： [1]Tetrahedron,2016,vol. 72,p. 6397 - 6408

54
[ 34698-41-4 ]
[ 1624255-71-5 ]
(R,S)-8-(2,3-dihydro-1H-inden-1-yl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino [2,1-f]purine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; at 20℃;	General procedure: 7-(2-Bromoethyl)-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (4) (100 mg, 0.32 mmol) was dissolved in dryCH2Cl2 (30 mL) and cooled to 0 C. A solution of PBr3 (90 lL,0.94 mmol) in dry CH2Cl2 (20 mL) was added dropwise. The solutionwas allowed to warm to rt and stirred for 1 h. Then it was cooled to0 C again and the excess of PBr3 was carefully hydrolyzed by slowaddition of saturated aq NaHCO3 solution (5 mL). The pH was set at8 by addition of more saturated aq NaHCO3 solution. Then, theorganic layer was separated and the aqueous layer extracted withCH2Cl2 (2 50 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. Thecrude 7-(2-bromoethyl)-8-bromo-1,3-dimethylpurine-2,4-dione (5) was dissolved in a mixture of dimethoxyethane (10 mL) anddiisopropylethylamine (DIPEA) (0.5 mL). Then, the appropriateamine (0.64 mmol)wasadded and the solutionwasstirred overnightat rt. The volatiles were removed under reduced pressure andtetrahydropyrazino[2,1-f]purinediones 6-63 precipitated uponaddition ofH2O(20 mL). For purification, thecompounds were eitherfiltered off and washed with H2O (3 5 mL) and subsequently withdiethylether (3 10 mL), or subjected to column chromatography(silica gel, gradient of CH2Cl2/MeOH 1:0 to 40:1).

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5462 - 5480

55
[ 34698-41-4 ]
[ 57-13-6 ]
[ 6520-67-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride; In water; for 2.5h;Reflux;	General procedure: Example 106A 1-[3-(Difluoromethyl)-2-methylbenzyl]urea 700 mg (4.08 mmol) of 1-[3-(difluoromethyl)-2-methylphenyl]methanamine from Example 105A and 982 mg (16.35 mmol) of urea were initially charged in 1.65 ml of water. 43 mul (0.52 mmol, purity 37%) of conc. hydrochloric acid were added dropwise, and the mixture was heated at reflux for 3 h. The cooled reaction mixture was diluted with water and stirred at RT for 30 min, the solid was filtered off with suction, washed with water and MTBE and dried under reduced pressure. This gave 719 mg (82% of theory) of the title compound. LC-MS (Method 3): Rt=0.71 min; m/z=215 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta=2.31 (s, 3H), 4.21 (d, 2H), 5.53 (s, 2H), 6.35 (t, 1H), 7.03-7.22 (m, 1H), 7.25-7.34 (m, 1H), 7.36-7.46 (m, 2H).

Reference： [1]Patent: US2016/297771,2016,A1 .Location in patent: Paragraph 0796; 0797; 0798; 0799; 0804; 0805; 0806; 0807

56
(E)-2,3-dihydro-1H-inden-1-one O-benzyloxime [ No CAS ]
[ 34698-41-4 ]

Yield	Reaction Conditions	Operation in experiment
80%Chromat.	With [Rh(OH)(cod)]2; Ureaphos-1; hydrogen; caesium carbonate; In isopropyl alcohol; at 55℃; under 97509.8 Torr; for 17h;Schlenk technique; Autoclave;	General procedure: A 50 mL Schlenk flask, equipped with a magnetic stirrer bar,was charged with [Rh(cod)(OH)]2 (2.81 mg = 6.2 lmol) and theselected chiral ligand (12.4 lmol in the case of a diphosphine).The reaction mixture was then conditioned by three vacuum/nitrogencycles and the degassed solvent (15 mL) was added followedby stirring at room temperature for 30 min before cannula transferinto a 50 mL double-walled stainless steel autoclave containing thesubstrate (1.24 mmol, 182.2 mg) and Cs2CO3 (199.8 mg,0.613 mmol). The autoclave was purged 3 times and pressurizedwith molecular hydrogen and the reaction was performed at thespecified temperature for 17 h. At the end of the reaction, the autoclavewas cooled to room temperature and slowly depressurized.The crude reaction mixture was filtered through a small pad of silicagel and analyzed by GC to determine conversions and yields.The enantiomeric excesses were determined by HPLC.

Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 268 - 273

57
[ 68253-35-0 ]
[ 34698-41-4 ]
N-(2,3-dihydro-1H-inden-1-yl)-2,3-dihydro-1H-inden-1-imine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%Chromat.	With [Rh(OH)(cod)]2; (R)-(S)-MeBophoz; hydrogen; caesium carbonate; In isopropyl alcohol; at 55℃; under 97509.8 Torr; for 17h;Schlenk technique; Autoclave;	General procedure: A 50 mL Schlenk flask, equipped with a magnetic stirrer bar,was charged with [Rh(cod)(OH)]2 (2.81 mg = 6.2 lmol) and theselected chiral ligand (12.4 lmol in the case of a diphosphine).The reaction mixture was then conditioned by three vacuum/nitrogencycles and the degassed solvent (15 mL) was added followedby stirring at room temperature for 30 min before cannula transferinto a 50 mL double-walled stainless steel autoclave containing thesubstrate (1.24 mmol, 182.2 mg) and Cs2CO3 (199.8 mg,0.613 mmol). The autoclave was purged 3 times and pressurizedwith molecular hydrogen and the reaction was performed at thespecified temperature for 17 h. At the end of the reaction, the autoclavewas cooled to room temperature and slowly depressurized.The crude reaction mixture was filtered through a small pad of silicagel and analyzed by GC to determine conversions and yields.The enantiomeric excesses were determined by HPLC.

Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 268 - 273

58
[ 34698-41-4 ]
6-bromo-4-cyclopropyl-1,3-dimethyl-3,4-dihydroquinoxalin-2(1H)-one [ No CAS ]
4-cyclopropyl-6-((2,3-dihydro-1H-inden-1-yl)amino)-1,3-dimethyl-3,4-dihydroquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 85℃;Sealed tube; Microwave irradiation; Inert atmosphere;	General procedure: To a solution of compound 93 (0.12 g, 0.41 mmol), sodium tert-butoxide (0.145 g, 1.51 mmol), phenylmethanamine (0.13 mL, 1.16 mmol) in toluene (5 mL) at room temperature were added palladium acetate (6 mg, 0.025 mmol) and tBu3P (0.017 mL, 0.07 mmol). The mixture was sealed in a microwave tube and heated to 85 C overnight. The reaction was monitored by TLC. Upon completion, the mixture was extracted with EtOAc (3 * 20 mL). The combined organic fractions were washed with brine, dried with Na2SO4, then concentrated by evaporation under reduced pressure. Purification by silica gel column chromatography (gradient elution, gradient 0-25% EtOAc/60-90 C petroleum ether) gave compound 32 as a yellow soild (0.077 g, 0.24 mmol, 59% yield).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 137,p. 176 - 195

59
[ 34698-41-4 ]
[ 32457-23-1 ]

Reference： [1]Patent: CN105061218,2017,B

60
[ 34698-41-4 ]
[ 7322-88-5 ]
N-((S)-2,3-dihydro-1H-inden-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With hydrogen; In toluene; at 55℃; under 7500.75 Torr; for 20h;Autoclave; Enzymatic reaction;	In the 1000ML autoclave,Followed by adding 500ML toluene,66.6G 1-aminoindane,115.9 g of L- (+) - O-acetylmandelic acid,4gCandida albicans lipaseAnd 6g KT-02,Sealed autoclave,The inside of the kettle is replaced with nitrogen,Then, hydrogen was introduced into the autoclave to a pressure of 1.0 MP,Open the stir,And the temperature was raised to 55 C to carry out the reaction;After 20 hours,Sampling detection,1-aminoindane is completely converted to the (S) -1-aminoindanyl acetyl compound;After the reaction,The solution was concentrated,Column chromatography,To obtain 81.9 g of an acetyl compound of pure (S) -1-aminoindan,The yield was 93.5%.

Reference： [1]Patent: CN105061218,2017,B .Location in patent: Paragraph 0007; 0008; 0009; 0014; 0015; 0016

61
[ 32315-10-9 ]
[ 13214-66-9 ]
[ 34698-41-4 ]
3-(2,3-dihydro-1H-inden-1-yl)-1-(4-phenylbutyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 8h;	General procedure: Next, the following Reaction Scheme 2 was referred to in order to prepare the compounds 3, 4, 13 to 22. First, amine (3.52 mmol) and N, N-diisopropylethylamine (DIPEA, N, N-diisopropylethylamine, 7.04 mmol) were added to a cold solution in which THF was dissolved in triphosgene The reaction mixture was stirred at room temperature for 8 hours, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with ethyl acetate Dried over sodium sulfate and concentrated under reduced pressure. The obtained crude product was separated by column chromatography to obtain compounds 3, 4, 13 to 22.

Reference： [1]Patent: KR2017/104218,2017,A .Location in patent: Paragraph 0108; 0109; 0110

62
[ 34698-41-4 ]
4-cyclopropyl-1,3-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylic acid [ No CAS ]
4-cyclopropyl-N-(2,3-dihydro-1H-inden-1-yl)-1,3-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		General procedure: To a solution of compound 65 (0.20g, 0.77mmol) in anhydrous DMF (1mL) was added HATU (0.29g, 0.77mmol), the mixture was stirred at rt for 30min, then DIPEA (0.13mL, 0.77mmol) and p-toluidine (0.083g, 0.77mmol) was added. The mixture was stirred at rt for another 12h and monitored by TLC. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc (3*20mL). The combined organic fractions were washed with brine, dried over Na2SO4, concentrated by evaporation under reduced pressure. Purification by silica gel column chromatography (gradient elution, gradient 0-25% EtOAc/60-90C petroleum ether) gave compound 7 (0.15g, 0.43mmol, 56% yield) as a white solid.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 156 - 175

63
[ 34698-41-4 ]
[ 68-12-2 ]
[ 31502-89-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With manganese(II) chloride tetrahydrate; at 150℃; for 10h;Inert atmosphere; Sealed tube;	The 1-aminoindan (26.6mg, 0.2mmol),Manganese chloride tetrahydrate (5.9 mg, 0.03 mmol),And a stirrer in the reaction tube,After replacing inert gas,Add 1 ml DMF,Seal the reaction tube.Place the reaction tube in a 150C oil bath reaction pot.Stir the reaction for 10 hours;After cooling to room temperature,Diluted with 15mL water,And extracted three times with ethyl acetate,15mL each time;Combine the extracts,Dry with anhydrous sodium sulfate and filter.The filtrate was concentrated under reduced pressure.With ethyl acetate:The crude product was purified by column chromatography with petroleum ether = 1:2 (containing 1% triethylamine) as eluent to give the pure product.Yellow solid,Melting point 109-110C,Yield 88%.
88%	With manganese(II) chloride tetrahydrate; at 150℃; for 10h;Sealed tube; Microwave irradiation; Inert atmosphere;	General procedure: A solution of amine (0.2 mmol) and MnCl2·4H2O (5.9 mg, 15 mol%) in DMF (1.0 mL) was stirred in a sealed microwave reaction tube under an atmosphere of argon at 150 C for 10 h. The mixture was cooled to r.t., and water (10 mL) was added; the mixture was extracted with EtOAc (3 × 15 mL). The combined organic layers were dried (anhyd Na2SO4), the solvent was evaporated under vacuum, and the crude product was purified by preparative TLC (silica gel, petroleum ether/EtOAc) to obtain the pure product.
80%	With cobalt(II) acetate; at 150℃; for 3h;Inert atmosphere; Sealed tube;	<strong>[34698-41-4]1-Aminoindan</strong>e (26.6 mg, 0.2 mmol), cobalt acetate tetrahydrate (7.5 mg, 0.03 mmol), and a stirrer were placed in the reaction tube. After replacing the inert gas, 1 ml of DMF was added to seal the reaction tube. .The reaction tube was placed in an oil bath at 150 C., stirred for 3 hours; cooled to room temperature, diluted with 15 mL of water, and extracted with ethyl acetate 3 times for 15 mL each; the extracts were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate:petroleum ether=1:2 (containing 1% triethylamine) as eluent to obtain a pure product. Yellow solid, yield 80%

69%	With molybdenum (IV) sulfide; at 150℃; for 18h;	<strong>[34698-41-4]1-Aminoindan</strong> (26.6 mg, 0.2 mmol), molybdenum disulfide (4 mg, 0.025 mmol), and a stirrer were placed in a reaction tube, and after replacing the inert gas, 1 ml of DMF was added to seal the reaction tube. The reaction tube was placed in a 150 C oil bath reaction pot, and the reaction was stirred for 18 hours; after cooling to room temperature, the catalyst was removed by filtration, the filtrate was diluted with 15 mL of water, and extracted with ethyl acetate three times, each time 15 mL; The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate: petroleum ether = 1:2 (1% triethylamine). Yellow solid, yield 69%.
52%	With graphene oxide; at 150℃; for 18h;Sealed tube;	1-aminoindole (26.6 mg, 0.2 mmol), graphene oxide (8 mg),And a stirrer is placed in the reaction tube, after replacing the inert gas,Add 1 ml of DMF and seal the reaction tube. Place the reaction tube at 150CIn the oil bath, stir the reaction for 18 hours; after cooling to room temperature,The catalyst was removed by filtration and the filtrate was diluted with 15 mL of water.And extracted with ethyl acetate 3 times, each time 15mL; combined extract,Dry with anhydrous sodium sulfate and filter. The filtrate is concentrated under reduced pressure.The crude product was subjected to column chromatography with ethyl acetate:petroleum ether=1:2 containing 1% triethylamine as eluent to obtain the pure product. Yellow solid, melting point 109-110C,Yield 52%.

Reference： [1]Patent: CN107986927,2018,A .Location in patent: Paragraph 0075; 0076
[2]Synthesis,2019,vol. 51,p. 693 - 703
[3]Patent: CN107892670,2018,A .Location in patent: Paragraph 0080; 0081
[4]European Journal of Organic Chemistry,2018,vol. 2018,p. 4940 - 4948
[5]Patent: CN107827817,2018,A .Location in patent: Paragraph 0079; 0080
[6]Patent: CN107827816,2018,A .Location in patent: Paragraph 0078; 0079

64
[ 29823-18-5 ]
[ 34698-41-4 ]
ethyl 7-(N-(2,3-dihydroindan-1-yl)amino)heptanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 45℃;Inert atmosphere; Sealed tube;	(+/-)-1-aminoindan (0.45 mL, 3.5 mmol) was dissolved in anhydrous ACN (10 mL) under N2, DIPEA (1.2 mL, 7.0 mmol) was added and let stir for 1 hour. Ethyl 7- bromoheptanoate (0.45 mL, 2.33 mmol) was then added drop-wise and the vial was sealed. The reaction vessel was heated to 45 and stirred overnight. The solution was allowed to cool to room temperature and the reaction quenched with H20 (10 mL). The mixture was extracted with CH2CI2 (3 chi 20 mL), the organic layers were combined and dried over MgS04. The solution was filtered, and the solvent was removed under reduced pressure followed by purification via column chromatography (EtOAc) giving (3-SI-1). Yield: 0.41 g (60%). 1H NMR (CDCb, 500MHz, 22 ): delta 7.38-7.34 (m, 1 H), 7.28-7.21 (m, 3H), 4.26 (t, 3JHH = 6.5 Hz, 1 H), 4.26 (q, 3JHH = 7.2 Hz, 2H), 3.06-2.98 (m, 1 H), 2.88-2.80 (m, 1 H), 2.73 (t, 3JHH = 7.2 Hz, 2H), 2.46-2.38 (m, 1 H), 2.32 (t, 3JM = 7.6 Hz, 2H), 1.89-1.81 (m, 1 H), 1.65 (q, 3JHH = 7.2 Hz, 2H), 1.55 (q, 3JM = 7.0 Hz, 2H), 1.44 (br. s, 1 H), 1.42-1.32 (m, 4H), 1.55 (t, 3JHH = 7.3 Hz, 3H)

Reference： [1]Patent: WO2018/45464,2018,A1 .Location in patent: Paragraph 0072

65
[ 34698-41-4 ]
(trans)-3-(3-chlorophenoxy)cyclobutanecarboxylic acid [ No CAS ]
racemic (trans)-3-(3-chlorophenoxy)-N-(2,3-dihydro-1H-inden-1-yl)cyclobutanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		To a DMF (4 mL) solution of (frans)-3-(3-chlorophenoxy)cyclobutanecarboxylic acid (Intermediate 122) (80 mg, 0.35 mmol) was added HATU (161 mg, 0.424 mmol) and N,N- diisopropylethylamine (0.19 mL, 1 .1 mmol). After 5 minutes, 1 -aminoindane (0.05 mL, 0.4 mmol) was added, and the mixture was stirred for 12 h, poured into water, and extracted with EtOAc (3X). The combined organic layers were dried over Na2SC>4, filtered and concentrated. This residue was purified on silica gel, eluting with 0%-100% EtOAc: EtOH (3:1) in hexanes to give the title compound (70 mg, 57%). 1H NMR (400 MHz, CD3SOCD3) delta 1 .74 (dd, J = 13, 8 Hz, 1 H), 2.14-2.24 (m, 2 H), 2.24-2.36 (m, 1 H), 2.61 (tt, J = 8, 4 Hz, 2 H), 2.76-2.82 (m, 1 H), 2.83-2.92 (m, 1 H), 3.05 (t, J = 5 Hz, 1 H), 4.88-4.91 (m, 1 H), 5.21 -5.30 (m, 1 H), 6.75-6.85 (m, 2 H), 6.95-6.98 (m, 1 H), 7.1 1 -7.19 (m, 3 H), 7.20-7.30 (m, 2 H), 8.22 (d, J = 8 Hz, 1 H); LC-MS (LC-ES) M+H = 342, 344 (CI pattern).

Reference： [1]Patent: WO2018/69863,2018,A1 .Location in patent: Page/Page column 453

66
[ 34698-41-4 ]
(R)-2-(1H-indazol-5-carboxamido)butanoic acid [ No CAS ]
C₂₁H₂₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 1h;	2,3-Dihydro-1H-indol-1-amine (43.1 mg, 323 mumol), diisopropylethylamine (167 mg, 1.29 mmol) was dissolved in N,N-dimethylformamide (5.00 mL) ,Then (R)-2-(1H-carbazole-5-formylamino)butyric acid is added in sequence(80.0 mg, 324 mumol),2-(7-oxobenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (123 mg, 324 mumol),After the reaction was stirred at room temperature for 1 hour, the solvent was evaporated under reduced pressure.Purification by preparative HPLC to give N-((2R)-((2,3-dihydro-1H-indol-1-yl)amino)-1-oxobutan-2-yl)-1H-indole Azole-5-carboxamide (14.1 mg, 38.1 mumol, yield 12%).

Reference： [1]Patent: CN108239081,2018,A .Location in patent: Paragraph 0089; 0097-0099

67
[ 34698-41-4 ]
[ 166818-85-5 ]
2-[(2,3-dihydro-1H-inden-1-yl)amino]-4-(4-methylpiperazin-1-yl)-1- nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;Inert atmosphere;	General procedure: To a rbf of l-(3-bromo-4-nitrophenyl)-4-methylpiperazine (0.045g, 0.150 mmol, 1 eq), (0760) Pd2(dba)3-CHC1 (1 mol%), rac-BINAP (2 mol%), and NaOtBu (0.017g, 0.180 mmol, 1.2 eq) was added anhydrous toluene (2.5 mL) and 1,2,3, 4-tetrahydronaphthalen- l -amine (0.045g, 0.150 mmol, 1 eq). The reaction was stirred under N2 at 100 C for 24 hours, after which the reaction was cooled, taken up in EtOAc, washed with water, dried (Na2S04), and concentrated. The crude product was purified on HPLC (5-95% MeCN:H20 with 0.1% TFA) to yield MBX 4048 (21 mg, 0.057 mmol, 38%). Yellow solid, mp 212-215 C. Rf: 0.75 (86: 13: 1 (0761) CHCl :MeOH:NH3). lH NMR (CDCb, 300 MHz, ppm) 8.67-8.65 (m, IH), 8.15-8.12 (m, IH), 7.26-7.17 (m, 4H), 6.21-6.18 (m, IH), 6.12-6.11 (m, IH), 4.79-4.77 (m, IH), 3.74-3.58 (m, 6H), 2.85 (m, 6H), 2.07- 1.96 (m, 5H). m/z: 367.2 (M+l)

Reference： [1]Patent: WO2018/106667,2018,A1 .Location in patent: Page/Page column 102; 103

68
[ 51991-94-7 ]
[ 34698-41-4 ]
N-(2,3-dihydro-1H-inden-1-yl)-5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925

69
[ 34698-41-4 ]
[ 474659-26-2 ]
N-(2,3-dihydro-1H-inden-1-yl)-7-(methyloxy)-3-quinolinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: N,N-Diisopropylethylamine (3.0-4.0 eq) was added to 8-methoxyquinoline-3-carboxylic acid (1.0 eq) in solvent (dichloromethane, tetrahydrofuran,or N,N-dimethylformamide, 0.05 to 0.2 M) at room temperature. Then, 1-((dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V)(1.0-1.5 eq) was added and the reaction mixture was stirred for five minutes. Then, amine (1.0 - 2.0 eq) was added and the reaction mixture was stirred for one to sixteen hours. 10% Aqueous citric acid was added and the reaction mixture was extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered,and concentrated. The resulting residue was purified by RP HPLC or silica gel chromatography to give the quinoline-3-carboxamide (1%-95% yield).

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1456 - 1478

70
[ 17640-21-0 ]
[ 34698-41-4 ]
N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-methoxyacetamide [ No CAS ]
(S)-1-Aminoindane [ No CAS ]
[ 1213099-69-4 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 4856 - 4866

71
[ 34698-41-4 ]
2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylacetic acid [ No CAS ]
2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-N-(2,3-dihydro-1H-inden-1-yl)-2-phenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a mixture of 2, 3-dihydro-1H-inden-1-amine (20 mg, 0.15 mmol) , 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylacetic acid (40 mg, 0.11 mmol) , DIEA (70 mg, 0.54 mmol) in DMF (2 mL) was added HATU (52 mg, 0.14 mmol) at rt and the mixture was stirred at rt for 16 hrs. 10 mL of EtOAc EA was added and the mixture was washed with brine (5 mL x 3) , dried over Na 2SO 4 and concentrated. The resulted residue was purified by prep-TLC (PE/EtOAc = 1: 1) to give the title product (33.0 mg, yield: 61%) . 1H NMR (400 MHz, DMSO-d6) delta 8.43 (t, J = 7.6 Hz, 1H) , 8.30 -8.03 (m, 3H) , 7.95 (s, 1H) , 7.47 (d, J = 7.2 Hz, 1H) , 7.44 -7.31 (m, 4H) , 7.29 -7.06 (m, 5H) , 6.81 -6.68 (m, 1H) , 6.46 (d, J = 9.6 Hz, 1H) , 5.36 (q, J = 8.0 Hz, 1H) , 2.91 -2.75 (m, 2H) , 2.43 -2.31 (m, 1H) , 1.89 -1.71 (m, 1H) . MS: M/e 491 (M+1) +.

Reference： [1]Patent: WO2019/196803,2019,A1 .Location in patent: Paragraph 0143

72
[ 70146-15-5 ]
[ 34698-41-4 ]

Reference： [1]Journal of Receptors and Signal Transduction,2020

73
[ 34698-41-4 ]
[ 15424-14-3 ]
2‐(2‐(1,3‐diphenyl‐1H‐1,2,4‐triazol‐5‐yl)phenyl)acetic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 3900 - 3904
Angew. Chem.,2020,vol. 132,p. 3928 - 3932,5

74
[ 34698-41-4 ]
[ 70146-15-5 ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 6216 - 6226

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	34698-41-4	MDL No. :	MFCD00003799
Formula :	C₉H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XJEVHMGJSYVQBQ-UHFFFAOYSA-N
M.W :	133.19	Pubchem ID :	123445
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.77
TPSA :	26.02 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.14 cm/s

Log Po/w (iLOGP) :	1.71
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	1.8
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	1.64

[ CAS No. 34698-41-4 ] {[proInfo.proName]}

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[ 34698-41-4 ] Synthesis Path-Upstream 1~1

[ 34698-41-4 ] Synthesis Path-Downstream 1~74

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[ 34698-41-4 ]

Aryls

Amines

Precautionary Statements-General

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Disposal

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.97
Solubility :	1.42 mg/ml ; 0.0106 mol/l
Class :	Very soluble
Log S (Ali) :	-1.52
Solubility :	4.03 mg/ml ; 0.0303 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.6
Solubility :	0.332 mg/ml ; 0.00249 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling