Name: 6373-50-8|4-Cyclohexylaniline|97%
Brand: Ambeed
SKU: A173712
Price: 5.0 USD
Availability: InStock
Rating: 90 (29 reviews)

1
[ 1747-75-7 ]
[ 6373-50-8 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 3403 - 3407
[2]Justus Liebigs Annalen der Chemie,1929,vol. 472,p. 34
[3]Patent: DE509045,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 17,p. 442

2
[ 5458-48-0 ]
[ 6373-50-8 ]

Yield	Reaction Conditions	Operation in experiment
0.805 g	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃;	A solution of the nitration compound 1 and Pd-C (10percent) in ethanol (100 mL) was stirred under hydrogen overnight at room temperature and then filtered through Celite and concentrated in vacuo. The crude product was purified by flash chromatography (PE:EtOAc = 20:1) to afford 0.805 g (46percent) compd. 2 and 0.219 g (17percent) compd. 2? as oil.

Reference： [1]Journal of the Chemical Society,1932,p. 2646,2652
[2]Journal of the American Chemical Society,1944,vol. 66,p. 914,917
[3]Journal of the Chemical Society,1958,p. 1184,1187
[4]Journal of the Chemical Society,1929,p. 507
[5]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1901,vol. 33,p. 697
Justus Liebigs Annalen der Chemie,1901,vol. 318,p. 323
[6]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 95,105
[7]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061

3
[ 6373-50-8 ]
[ 25109-28-8 ]

Reference： [1]Journal of the American Chemical Society,1940,vol. 62,p. 1550,1552
[2]Journal of the Chemical Society,1929,p. 507

4
[ 3282-99-3 ]
[ 6373-50-8 ]

Reference： [1]Patent: CH143386,1929,
[2]Patent: DE557517,1929,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 688
[3]Patent: DE557517,1929,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 688
[4]Justus Liebigs Annalen der Chemie,1929,vol. 472,p. 34
[5]Justus Liebigs Annalen der Chemie,1929,vol. 472,p. 34
[6]Patent: DE553626,1928,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 18,p. 820

5
[ 6373-50-8 ]
[ 98-88-4 ]
4'-cyclohexylbenzanilide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 4h;	General procedure: A mixture of Compound 193C (278 mg, 1.32 mmol), benzoyl chloride (228 mg, 1.62 mmol), DMAP (36 mg, 0.294 mmol) and triethylamine (297 mg, 2.94 mmol) indichloromethane (30 mL) was stirred at room temperature for 4 hours. The mixture was washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2S04, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 20% v/v) to give compound 193D. LC-MS (ESI) m/z: 315 [M+H]+; 'H-NMR (CD3OD, 400 MHz): d (ppm) 1.73-1.83 (m, 2H), 2.03-2.06 (m, 2H), 2.83-2.89 (m, 2H), 3.71-3.75 (m, 2H), 4.03-4.07 (m, 1H), 6.96-7.01 (m, 2H), 7.20 (d, J= 8.8 Hz, 2H), 7.44-7.48 (m, 2H), 7.51-7.56 (m, 1H), 7.83 (m, J = 7.6 Hz, 2H).

Reference： [1]Il Farmaco,2002,vol. 57,p. 777 - 782
[2]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 205 - 212
[3]Patent: WO2019/133770,2019,A2 .Location in patent: Paragraph 001216; 001217; 001219; 001221; 001222; 001223

6
[ 6373-50-8 ]
[ 5736-88-9 ]
[1-(4-Butoxy-phenyl)-meth-(E)-ylidene]-(4-cyclohexyl-phenyl)-amine [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 159,p. 37 - 52

7
[ 6373-50-8 ]
1-Cyclohexyl-4-nitroso-benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1326 - 1332

8
[ 1943-83-5 ]
[ 6373-50-8 ]
[ 74746-36-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3526 - 3531
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 694 - 702
[3]European Journal of Medicinal Chemistry,1994,vol. 29,p. 963 - 966
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6063 - 6068

9
[ 6373-50-8 ]
[ 3312-60-5 ]
[ 142666-93-1 ]
<i>N</i>-(3-cyclohexylamino-propyl)-3-[(4-cyclohexyl-phenylcarbamoyl)-methyl]-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 503 - 507

10
[ 6373-50-8 ]
[ 98-86-2 ]
6-cyclohexyl-2-methyl-2,4-diphenyl-1,2-dihydro-quinoline [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 3907 - 3910

11
4-dimethylamino-5-(dimethylaminomethyleneamino)thieno[8,9-b]pyridine-6-carboxylic acid methyl ester [ No CAS ]
[ 6373-50-8 ]
3-(4-Cyclohexyl-phenyl)-9-dimethylamino-3H-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7374 - 7388

12
[ 3592-25-4 ]
[ 6373-50-8 ]
[ 267428-39-7 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 3721 - 3730

13
[ 463-71-8 ]
[ 6373-50-8 ]
[ 78290-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 1h;	To a stirring solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (10 mmol, 1.75 g) and DIEA (21 mmol, 3.65 mL) in CH2C12 (10 mL) at 0 °C was added thiophosgene (10 mmol, 700 pL) dropwise. The solution was allowed to reach ambient temperature for 1 h, and 4, 5-dichloro-1, 2- phenylenediamine (10.5 mmol, 1.86 g) was added. The reaction mixture was heated to reflux for 2 h, then concentrated in vacuo. The residue was taken up in a solution of EtOH (5 mL) and MeI (20 mmol, 1.25 mL), heated at 40 °C for 16 h, and concentrated in vacuo. Flash chromatography on silica eluting with 18-25percent EtOAc in hexanes afforded the product as a red solid. LC-MS (ESI, Method C): 3.47 min, m/z 360.2 (M+1).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 172 - 175
[2]Patent: WO2005/65680,2005,A1 .Location in patent: Page/Page column 51-52

14
[ 798538-84-8 ]
[ 6373-50-8 ]
[ 798538-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With nido-decaborane; In methanol; for 60h;	INTERMEDIATE 5; Butyl 1 -r(4-cyclohexylphenv?amino1indane-5-carboxylateA mixture of butyl l-oxoindane-5-carboxylate (2.00 g, 8.60 mmol), <strong>[6373-50-8]4-cyclohexylaniline</strong> (2.28 g, 13.00 mmol), decaborane (0.32 g, 2.60 mmol) in dry MeOH (30 mL) was stirred under nitrogen for 60 h. Yellow precipitates were collected by filtration and washed with MeOH (3 x 5 mL) to give butyl l-[(4-cyclohexylphenyl)amino]indane-5-carboxylate as a white solid. HPLC/MS: m/z = 392.6 (M+l), Rt = 4.97 min. 1H NMR (CDCl3): delta 8.00 (IH, s), 7.97(1H, d, J= 8.0 Hz), 7.48 (IH, d, J= 8.0 Hz), 7.14 (2H, d, J= 8.0 Hz), 6.74 (2H, d, J= 8.0 Hz), 5.07 (IH, t, J= 7.0 Hz), 4.39 (2H, t, J= 6.5 Hz), 3.92 (IH, br s), 3.12-3.07 (IH, m), 3.00-2.94 (IH, m), 2.72-2.66 (IH, m), 2.52-2.47 (IH, m), 2.02-1.80 (8H, m), 1.60-1.31 (7H, m), 1.08 (3H, t, J= 7.5 Hz).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592
[2]Patent: WO2006/104826,2006,A2 .Location in patent: Page/Page column 24

15
4-hydroxy-2-oxo-6-phenyl-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester [ No CAS ]
[ 6373-50-8 ]
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-6-phenyl-1,2-dihydropyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	In N,N-dimethyl-formamide; at 180℃; for 0.333333h;Microwave irradiation;	To a solution of 7 (30 mg, 0.12 mmol) in DMF was added 4-cyclohexy!aniline (30 mg, 0.17 mmol) and the resulting mixture was heated in a microwave synthesizer at 18G C for 10 min. After sitting at room temperature for 10 mm, the reaction mixture turned into a suspension and was filtered and rinsed with MeOH to afford the title compound as a white crystalline solid (10 mg, 22percent). MS (ES+): m/z = 389 (M+l) 1H NMR (400 MHz, DMSO-D6) 8 = 1.24 (m, I H) 1.31 - 1.42 (m, 4 H) 1.70 (d, j=12.63 Hz, 1 H) 1.78 (d, j=9.09 Hz, 4 H) 6.45 (s, 1 H) 7.24 (d, j=8.59 Hz, 2 H) 7.50 - 7.58 (in, 5 H) 7.77 - 7.84 (m, 2 H) 12.17 (s, 1 H) 12,46 (s, 1 H) 15,29 (s, ! H).

Reference： [1]Patent: WO2008/14311,2008,A2 .Location in patent: Page/Page column 169

16
[ 6373-50-8 ]
[ 115411-39-7 ]
4-hydroxy-2-oxo-6-phenyl-2H-pyran-3-carboxylic acid (4-cyclohexylphenyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	In tetrahydrofuran; at 170℃; for 0.116667h;Microwave irradiation;	To a solution of 15 ( 52.2 rag, (Urnmol) in THF (1.5 mL) was added 4-cyclohexyl aniline (35mg, 0.24 mmo3). The reaction mixture was heated at 120 C in a microwave synthesizer for 7 min. The mixture was concentrated and triturated with ether to afford the title compound as a white solid (6.6 mg, 20percent), MS (ES+): m/z = 405 (M+l) 1H NMR (400 MHz, DMSO-D6) 8 = 1.24 (m, 1 H) 1.37 (t, j=10.61 Hz,5 H) 1.70 (d, ,7-12.63 Hz, 1 H) 1.78 (d, ,7-9.09 Hz, 5 H) 2.73 (m, 2 H) 2.95 (s, 1 H) 3.06 (s, 1 H) 3.14 - 3.23 (m, 1 H) 7.19 - 7.27 (ra, 5 H) 7,31 (d, j=7.07 Hz, 2 H) 7.42 (d, i=8.08 Hz, 2 H)

Reference： [1]Patent: WO2008/14311,2008,A2 .Location in patent: Page/Page column 179

17
[ 1005188-00-0 ]
[ 6373-50-8 ]
5-benzyl-4-hydroxy-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid (4-cyclohexyl-phenyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.25%	In tetrahydrofuran; at 170℃; for 0.0833333h;Microwave irradiation;	To a solution of 22 ( 52.2 rag, (Urnmol) in THF (1.5 mL) was added 4-cyclohexyl aniline (35mg, 0.24 mmo3). The reaction mixture was heated at 120 C in a microwave synthesizer for 5 min. The mixture was concentrated and triturated with ether to afford the title compound as a white solid (6.6 mg, 8.25percent), MS (ES+): m/z = 405 (M+l) 1H NMR (400 MHz, DMSO-D6) 8 = 1.24 (m, 1 H) 1.37 (t, j=10.61 Hz,5 H) 1.70 (d, ,7-12.63 Hz, 1 H) 1.78 (d, ,7-9.09 Hz, 5 H) 2.73 (m, 2 H) 2.95 (s, 1 H) 3.06 (s, 1 H) 3.14 - 3.23 (m, 1 H) 7.19 - 7.27 (ra, 5 H) 7,31 (d, j=7.07 Hz, 2 H) 7.42 (d, i=8.08 Hz, 2 H)

Reference： [1]Patent: WO2008/14311,2008,A2 .Location in patent: Page/Page column 179-179-A

18
[ 854382-06-2 ]
[ 6373-50-8 ]
N-(4-Cyclohexylphenyl){2-[(4-pyridylmethyl)amino](3-pyridyl)}carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6003 - 6008

19
[ 827-52-1 ]
[ 6373-50-8 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 159,p. 37 - 52
[2]Journal of the Chemical Society,1958,p. 1184,1187
[3]Journal of the Chemical Society,1932,p. 2646,2652
[4]Journal of the Chemical Society,1929,p. 507
[5]Journal of the Chemical Society,1929,p. 507
[6]Journal of the Chemical Society,1929,p. 507
[7]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 95,105
[8]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061
[9]Nature Chemistry,2019,vol. 11,p. 71 - 77
[10]Patent: CN109134267,2019,A

20
tin (II) chloride dihydrate [ No CAS ]
[ 6373-50-8 ]
[ 126062-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium nitrite; In hydrogenchloride; methanol; ethanol; water;	Preparation of 4-Cyclohexylphenylhydrazine hydrochloride (Intermediate A) To a slurry a <strong>[6373-50-8]4-cyclohexylaniline</strong> (350.6 g) and ethanol (330 ml) in 30percent HCl (1470 ml) was added a solution of sodium nitrite (151.8 g) in water (735 ml), while maintaining the temperature between -8 to -2°C. The reaction was stirred for an additional four hours at -2 to 10°C. A solution of tin (II) chloride dihydrate (1353.8 g) in 30percent HCl (1470 ml) was added slowly, and the resulting white suspension was cooled overnight. The crude product was collected by vacuum filtration and washed with 1 N hydrochloric acid, and ether. Recrystallization in 6 L of methanol gave 300 g of the desired product as fine long needles, m.p. 251-254°C.

Reference： [1]Patent: EP596983,1995,B1

21
[ 6373-50-8 ]
[ 686265-49-6 ]

Yield	Reaction Conditions	Operation in experiment
31%		A solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.877 g, 5.0 mmol, 1.0 eq) in nitroethane (5 ML) was cooled to -40° C., treated dropwise with chlorosulfonyl isocyanate (0.87 g, (0.523 ML, 6.15 mmol, 1.23 eq), warmed to 0° C., treated with aluminum trichloride (0.85 g, 6.35 mmol, 1.27 eq), heated in a 110° C. oil bath for 30 minutes, cooled to ambient temperature, and poured into 200 ML of ice water.The mixture was filtered and the filter cake was rinsed with cold water, dissolved in 50percent H2SO4 (25 ML), heated to reflux for 4 hours, cooled to ambient temperature, poured into 200 ML of ice water, and carefully neutralized to PH 7 with 40percent NaOH. The reaction mixture was extracted with ethyl acetate (3*100 ML) and the combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.40 g of the desired product (31percent yield). MS (ESI+) m/z 255.0 (M+H)+, 272.1 (M+H2O)+, 277.0 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) delta 1.32 (m 4H), 1.71 (m, 6H), 2.36 (m, 1H), 5.64 (s, 2H), 6.72 (d, J=8.09 Hz, 1H), 7.11 (dd, J=8.46, 2.21 Hz, 1H), 7.16 (s, 2H), 7.38 (d, J=2.21 Hz, 1H).

Reference： [1]Patent: US2004/87577,2004,A1 .Location in patent: Page 60

22
[ 1189-71-5 ]
[ 6373-50-8 ]
[ 686265-49-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium hydroxide; aluminium trichloride; In Nitroethane; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid;	Example 86A 2-amino-5-cyclohexylbenzenesulfonamide A solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.877 g, 5.0 mmol, 1.0 eq) in nitroethane (5 mL) was cooled to -40° C., treated dropwise with chlorosulfonyl isocyanate (0.87 g, (0.523 mL, 6.15 mmol, 1.23 eq), warmed to 0° C., treated with aluminum trichloride (0.85 g, 6.35 mmol, 1.27 eq), heated in a 110° C. oil bath for 30 minutes, cooled to ambient temperature, and poured into 200 mL of ice water. The mixture was filtered and the filter cake was rinsed with cold water, dissolved in 50percent H2SO4 (25 mL), heated to reflux for 4 hours, cooled to ambient temperature, poured into 200 mL of ice water, and carefully neutralized to pH 7 with 40percent NaOH. The reaction mixture was extracted with ethyl acetate (3*100 mL) and the combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.40 g of the desired product (31percent yield). MS (ESI+) m/z 255.0 (M+H)+, 272.1 (M+H2O)+, 277.0 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) delta 1.32 (m 4H), 1.71 (m, 6H), 2.36 (m, 1H), 5.64 (s, 2H), 6.72 (d, J=8.09 Hz, 1H), 7.11 (dd, J=8.46, 2.21 Hz, 1H), 7.16 (s, 2H), 7.38 (d, J=2.21 Hz, 1H).
31%		2-amino-5-cyclohexylbenzenesulfonamide A solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.877 g, 5.0 mmol, 1.0 eq) in nitroethane (5 ML) was cooled to -40° C., treated dropwise with chlorosulfonyl isocyanate (0.87 g, (0.523 ML, 6.15 mmol, 1.23 eq), warmed to 0° C., treated with aluminum trichloride (0.85 g, 6.35 mmol, 1.27 eq), heated in a 110° C. oil bath for 30 minutes, cooled to ambient temperature, and poured into 200 ML of ice water.The mixture was filtered and the filter cake was rinsed with cold water, dissolved in 50percent H2SO4 (25 ML), heated to reflux for 4 hours, cooled to ambient temperature, poured into 200 ML of ice water, and carefully neutralized to PH 7 with 40percent NaOH. The reaction mixture was extracted with ethyl acetate (3*100 ML) and the combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.40 g of the desired product (31percent yield). MS (ESI+) m/z 255.0 (M+H)+, 272.1 (M+H2O)+, 277.0 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) delta 1.32 (m 4H), 1.71 (m, 6H), 2.36 (m, 1H), 5.64 (s, 2H), 6.72 (d, J=8.09 Hz, 1H), 7.11 (dd, J=8.46, 2.21 Hz, 1H), 7.16 (s, 2H), 7.38 (d, J=2.21 Hz, 1H).

Reference： [1]Patent: US2004/162285,2004,A1
[2]Patent: US2004/167123,2004,A1 .Location in patent: Page/Page column 93

23
[ 6373-50-8 ]
[ 1390667-44-3 ]
[ 6639-95-8 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture OF 4-CYCLOHEXYLANILINE (10. 0G, 57.1 MMOL) and acetic anhydride (50ML) was stirred at 50°C for 1 hour. The resultant mixture was cooled in an ice-bath and a solution of potassium nitrate (10. 0G, 99. OMMOL) in CONC. sulphuric acid (25ML) was added drop-wise keeping the temperature at 15-18°C. After the addition, the mixture was poured into ice-water (400g). The precipitate was filtered off, washed with water and dried. This crude product (12g) contained a 1: 1 mixture of mono-and dinitrated product. The desired product was isolated by column chromatography on silica gel, using a mixture of petroleum ether and ethyl acetate (9: 1, v/v) as the eluent (6.5g).

Reference： [1]Patent: WO2004/87137,2004,A1 .Location in patent: Page/Page column 21

24
[ 307989-22-6 ]
[ 6373-50-8 ]
[ 307989-23-7 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a well stirred solution of 3-(4-formylbenzoylamino)propionic acid ethyl ester (13.8 g, 55.3 mmol) in ethanol (150 mL) was added a solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (9.70 g, 55.3 mmol) in ethanol (75 mL). The mixture was heated to reflux for 30 minutes, and then acetic acid (50 mL) and sodium cyanoborohydride (3.50 g, 55.5 mmol) were added. After 10 minutes of additional heating, the mixture was cooled on an ice-bath. The solid precipitate was collected by filtration, washed several times with cold water and dried in a vacuum oven overnight to afford 18.16 g (80percent) of 3-{4-[(4-cyclohexylphenylamino)methyl]benzoylamino}propionic acid ethyl ester.1H NMR (CDCl3): delta 1.28 (t, 3H); 1.35 (m, 5H); 1.78 (m, 5H); 2.38 (m, 1H); 2.64 (t, 2H); 3.74 (q, 2H); 4.18 (q, 2H); 4.36 (s, 2H); 6.53 (d, 2H); 6.81 (bt, 1H); 7.00 (d, 2H); 7.43 (d, 2H); 7.72 (d, 2H).
18.16 g (80%)	With sodium cyanoborohydride; acetic acid; In ethanol;	To a well stirred solution of 3-(4-formylbenzoylamino)propionic acid ethyl ester (13.8 g, 55.3 mmol) in ethanol (150 mL) was added a solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (9.70 g, 55.3 mmol) in ethanol (75 mL). The mixture was heated to reflux for 30 minutes, and then acetic acid (50 mL) and sodium cyanoborohydride (3.50 g, 55.5 mmol) were added. After 10 minutes of additional heating, the mixture was cooled on an ice-bath. The solid precipitate was collected by filtration, washed several times with cold water and dried in a vacuum oven overnight to afford 18.16 g (80percent) of 3-{4-[(4-cyclohexylphenylamino)methyl]benzoylamino}propionic acid ethyl ester. 1H NMR (CDCl3): delta1.28 (t, 3H); 1.35 (m, 5H); 1.78 (m, 5H); 2.38 (m, 1H); 2.64 (t, 2H); 3.74 (q, 2H); 4.18 (q, 2H); 4.36 (s, 2H); 6.53 (d, 2H); 6.81 (bt, 1H); 7.00 (d, 2H); 7.43 (d, 2H); 7.72 (d, 2H).

Reference： [1]Patent: EP1183229,2005,B1 .Location in patent: Page/Page column 135
[2]Patent: US6503949,2003,B1

25
[ 307989-39-5 ]
[ 6373-50-8 ]
[ 307989-40-8 ]

Yield	Reaction Conditions	Operation in experiment
83.5%		4-Formyl-N-(2H-tetrazol-5-yl)benzamide (8.94 g, 41.2 mmol) was dissolved in DMF (50 mL) by gentle heating. A solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (7.20 g, 41.2 mmol) in methanol (100 mL) was added and a turbid suspension was formed. The suspension was heated to 70°C for 1 hour. Acetic acid (50 mL) and sodium cyanoborohydride (2.0 g, 31.7 mmol) was then added. The turbid suspension was heated to 70°C for an additional hour, before being cooled to 0°C on an ice bath. The insoluble material was collected by filtration and washed twice with water, before being dried overnight in a vacuum oven to afford 12.94 g (83.5percent) of 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide.1H NMR (DMSO-d6): delta 1.28 (m, 5H); 1.68 (m, 5H); 2.28 (m, 1H); 4.32 (s, 2H); 6.17 (bs, 1H); 6.48 (d, 2H); 6.88 (d, 2H); 7.52 (d, 2H); 8.03 (d, 2H); 12.30 (s, 1H).
12.94 g (83.5%)	With sodium cyanoborohydride; acetic acid; In methanol; N,N-dimethyl-formamide;	4-Formyl-N-(2H-tetrazol-5-yl)benzamide (8.94 g, 41.2 mmol) was dissolved in DMF (50 mL) by gentle heating. A solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (7.20 g, 41.2 mmol) in methanol (100 mL) was added and a turbid suspension was formed. The suspension was heated to 70° C. for 1 hour. Acetic acid (50 mL) and sodium cyanoborohydride (2.0 g, 31.7 mmol) was then added. The turbid suspension was heated to 70° C. for an additional hour, before being cooled to 0° C. on an ice bath. The insoluble material was collected by filtration and washed twice with water, before being dried overnight in a vacuum oven to afford 12.94 g (83.5percent) of 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide. 1H NMR (DMSO-d6): delta1.28 (m, 5H); 1.68 (m, 5H); 2.28 (m, 1H); 4.32 (s, 2H); 6.17 (bs, 1H); 6.48 (d, 2H); 6.88 (d, 2H); 7.52 (d, 2H); 8.03 (d, 2H); 12.30 (s, 1H).

Reference： [1]Patent: EP1183229,2005,B1 .Location in patent: Page/Page column 171
[2]Patent: US6503949,2003,B1

26
C₉H₆N₅O₂Pol [ No CAS ]
[ 6373-50-8 ]
C₂₁H₂₃N₆OPol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The above resin bound 4-formyl-N-(2H-tetrazol-5-yl)benzamide (50 mg) was treated with a 0.5 M solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.25 mmol, 41.25 mg) in a mixture of DMF and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 muL) for 1 hour at 25°C followed by sodium cyanoborohydride (250 mumol, 16 mg) dissolved in a mixture of DMF and methanol (1:1, 0.25 mL). Shaking at 25°C for 4 hours followed by filtration and washing with a mixture of DMF and methanol (1:1, 2x1 mL), 3 x 1 mL DMF and 2 x 1 mL dichloromethane afforded the desired product.

Reference： [1]Patent: EP1183229,2005,B1 .Location in patent: Page/Page column 154

27
[ 24851-69-2 ]
[ 6373-50-8 ]
N-4-cyclohexylphenyl-2-methyl-1,3-benzothiazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h;	iV-4-cyclohexylphenyl-2-methyl-l,3-benzothiazole-5-carboxamide. 2-Methyl-l,3-benzothiazole-5-carboxylic acid (100 mg, 0.440 mml) was dissolved in DMF (5.00 mL), and HATU (190 mg, 0.500 mmol), 4-cyclohexylaniline (88.0 mg, 0.500 mmol) and Et3N (0.100 mL) were added. The mixture was stirred for 3 hours, and the solvents were evaporated. The product was purified by flash chromatography on silica gel eluting with mixtures of hexane and EtO A.c (9: 1 to 4: 1) to yield a mostly pure product, which was recrystallized from heptanes and EtOAc to yield a pure product (15.1 mg, 0.043 mmol, 10.0%). 1H NMR (400 MHz, DMSO-D6) delta ppm 1.15 - 1.50 (m, 5 H) 1.60 - 1.83 (m, 6 H) 2.82 (s, 3 H) 7.18 (d, J=8.59 Hz, 2 H) 7.67 (d, J=8.59, 2 H) 7.94 (dd, J=8.40, 1.76 Hz, 1 H) 8.14 (d, J=8.40 Hz, 1 H) 8.48 (d, J=I.56 Hz, 1 H) 10.30 (s, 1 H); MS [M+] calcd. 350.2, found 351.0.

Reference： [1]Patent: WO2006/68592,2006,A1 .Location in patent: Page/Page column 20

28
[ 873190-02-4 ]
[ 6373-50-8 ]
5-methanesulfonyl-2-methyl-4-oxo-3,4-dihydro-thieno[3,4-d]pyrimidine-7-carboxylic acid (4-cyclohexylphenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃; for 12h;	5-Methanesulfonyl-2-methyl-4-oxo-3,4-dihydrothieno[3,4-d]pyrimidine-7-carboxylicacid (20 mg, 70u.mol) was dissolved in DMF (0.60 ml) and GDI (12.4 mg, 77 \|amol) wasadded. The reaction was shaken in a glass vial for 30 min. before 4-cyclohexylanilin (13.4mg, 77 \|amol) was added. The reaction was heated with a heat gun until the starting materialdissolved. The reaction mixture was shaken 12 h at rt before it was poured into H2O (2 ml).The precipitate was filtered off and washed with H2O (3x10 ml). The compound was dried16 h in vacua at 50°C to give 15 mg (50percent) of 5-methanesulfonyl-2-methyl-4-oxo-3,4-dihydro-thieno[3,4-d]pyrimidine-7-carboxylic acid (4-cyclohexylphenyl) amide.

Reference： [1]Patent: WO2006/3096,2006,A1 .Location in patent: Page/Page column 68

29
CH₂Cl₂-Hexane [ No CAS ]
[ 288398-37-8 ]
[ 6373-50-8 ]
[ 3375-31-3 ]
[ 288397-99-9 ]

Yield	Reaction Conditions	Operation in experiment
73.8 mg (45%)	With caesium carbonate; In toluene;	a) Methyl 4-[(4-cyclohexylphenyl)amino]-5-methylthiothiophene -2-carboxylate The same procedure as in Example 197, step (a) was followed using 122 mg (0.457 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate (as prepared in Example 241, step (a)), 9.9 mg (9.7 mol percent) of palladium (II) acetate, 42.3 mg (14.9 mol percent) of racemic-BINAP, 206 mg (0.632 mmol) of cesium carbonate, 102 mg (0.582 mmol) of <strong>[6373-50-8]4-cyclohexylaniline</strong> and 913 muL of toluene, and chromatographed as before using 20-40percent CH2Cl2-hexane to afford 73.8 mg (45percent) of the title compound as a light green resin: 1H-NMR (CDCl3, 400 MHz) delta7.74 (s, 1 H), 7.15 (d, 2 H, J=8.4 Hz), 6.98 (d, 2 H, J=8.4 Hz), 6.12 (s, 1 H), 3.88 (s, 3 H), 2.48 (m, 1 H), 2.39 (s, 3 H), 1.87 (m, 4 H), 1.76 (br d, 1 H, J=12.5 Hz), 1.41 (m, 4 H) and 1.28 (m, 1 H). Mass spectrum (ESI, m/z): Calcd. for C19H23NO2S2, 362.1 (M+H), found 362.4.
73.8 mg (45%)	With caesium carbonate; In toluene;	a) Methyl 4-[(4-cyclohexylphenyl)amino]-5-methylthiothiophene-2-carboxylate The same procedure as in Example 197, step (a) was followed using 122 mg (0.457 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate (as prepared in Example 241, step (a)), 9.9 mg (9.7 mol percent) of palladium (II) acetate, 42.3 mg (14.9 mol percent) of racemic-BINAP, 206 mg (0.632 mmol) of cesium carbonate, 102 mg (0.582 mmol) of <strong>[6373-50-8]4-cyclohexylaniline</strong> and 913 muL of toluene, and chromatographed as before using 20-40percent CH2Cl2-hexane to afford 73.8 mg (45percent) of the title compound as a light green resin: 1H-NMR (CDCl3, 400 MHz) delta 7.74 (s, 1H), 7.15 (d, 2H, J=8.4 Hz), 6.98 (d, 2H, J=8.4 Hz), 6.12 (s, 1H), 3.88 (s, 3H), 2.48 (m, 1H), 2.39 (s, 3H), 1.87 (m, 4H), 1.76 (br d, 1H, J=12.5 Hz), 1.41 (m, 4H) and 1.28 (m, 1H). Mass spectrum (ESI, m/z): Calcd. for C19H23NO2S2, 362.1 (M+H), found 362.4.

Reference： [1]Patent: US2002/37915,2002,A1
[2]Patent: US6291514,2001,B1

30
[ 307989-39-5 ]
[ 6373-50-8 ]
[ 149-73-5 ]
[ 307989-40-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;	Step B: Resin Bound 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide The above resin bound 4-formyl-N-(2H-tetrazol-5-yl)benzamide (50 mg) was treated with a 0.5 M solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.25 mmol, 41.25 mg) in a mixture of DMF and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 muL) for 1 hour at 25° C. followed by sodium cyanoborohydride (250 mumol, 16 mg) dissolved in a mixture of DMF and methanol (1:1, 0.25 mL). Shaking at 25° C. for 4 hours followed by filtration and washing with a mixture of DMF and methanol (1:1, 21 mL), 31 mL DMF and 2*1 mL dichloromethane afforded the desired product.

Reference： [1]Patent: US6503949,2003,B1
[2]Patent: US6503949,2003,B1

31
[ 41118-21-2 ]
[ 6373-50-8 ]
[ 911376-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With nido-decaborane; In methanol; for 60h;	INTERMEDIATE 7; Methyl 4-[(4-cvclohexylphenyl)amino1chromane-7-carboxylate A mixture of <strong>[41118-21-2]methyl 4-oxochromane-7-carboxylate</strong> (1.50 g, 7.27 mmol), 4- cyclohexylaniline (2.55 g, 14.55 mmol), decaborane (0.27 g, 2.18 mmol) in dry MeOH (15 mL) was stirred under nitrogen for 60 h. Solvent evaporation in vacuo and chromatography (8% EtOAc in Hexane) gave methyl 4-[(4-cyclohexylphenyl)amino]chromane-7-carboxylate as a slightly yellow solid. HPLC/MS: m/z = 365.2 (M+l), Rt = 2.56 min. 1H NMR (CDCl3): delta 7.59 (IH, dd, J= 2.0 Hz, 8.0 Hz), 7.56 (IH, d, J= 2.0 Hz), 7.43 (IH, d, J= 8.0 Hz), 7.12 (2H, d, J= 8.5 Hz), 6.69 (2H, d, J= 8.5 Hz), 4.68 (IH, t, J= 4.5 Hz), 4.35-4.26 (2H, m), 3.95 (3H, s), 3.86 (IH, br s), 2.46 (IH, m), 2.20 (2H, dd, J= 4.5 Hz, 10.5 Hz), 1.92-1.87 (4H, m), 1.80-1.77 (IH, m), 1.43 (4H, m), 1.29 (IH, m).The racemic methyl 4-[(4-cyclohexylphenyl)amino]chromane-7-carboxylate was resolved on ChiralPak AD column with 15% IPA in n-Heptane to give enantiomer A (-), Rt = 14.48 min and B (+), Rt = 16.01 min

Reference： [1]Patent: WO2006/104826,2006,A2 .Location in patent: Page/Page column 25

32
[ 6373-50-8 ]
[ 144464-66-4 ]
[ 911376-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	With nido-decaborane In methanol for 4h;	6 INTERMEDIATE 6; Methyl 5-r(4-cvclohexylphenyl)amino]-5,6,7,8-tetrahvdronaphthalene-2-carboxylateA mixture of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (1.2 g, 5.9 mmol), 4-cyclohexylaniline (2.1 g, 11.8 mmol), decaborane (0.22 g, 1.8 mmol) in dry MeOH (20 mL) was stirred under nitrogen for 4 h. Solvent evaporation and chromatography (5% to 20% EtOAc in EPO Hexane) gave methyl 5-[(4-cyclohexylphenyl)amino]-5,6,7,8-tetrahydronaphthalene-2-carboxylate as a yellow solid. HPLC/MS: nVz = 364.2 (M+l), R4 = 2.83 min. 1H NMR (CDCl3): δ 7.86 (IH, s), 7.85(1H, d, J= 7.5 Hz), 7.54 (IH, d, J= 7.5 Hz), 7.11 (2H, d, J= 8.5 Hz), 6.68 (2H, d, J= 8.5 Hz), 4.66 (IH, t, J= 5.5 Hz), 3.96 (3H, s), 3.79 (IH, br s), 2.97-2.82(2H, m), 2.46 (IH, m), 2.10-1.78 (9H, m), 1.44 (4H, m), 1.30 (IH, m).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2006/104826, 2006, A2 Location in patent: Page/Page column 24-25

33
Cu₂ O [ No CAS ]
[ 6373-50-8 ]
[ 292638-85-8 ]
methyl 2-bromo-3-(4-cyclohexylphenyl)propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With aqueous HBr; sodium nitrite; In water; acetone;	REFERENCE EXAMPLE 16 In acetone (400 ml) was dissolved <strong>[6373-50-8]4-cyclohexylaniline</strong> (50 g) followed by addition of 47percent aqueous HBr (147 g). Then, a solution of NaNO2 (21.6 g) in water (30 ml) was added dropwise at 0°-5° C. and the mixture was stirred at 5° C. for an additional 30 minutes. Thereafter, the reaction mixture was warmed to 15° C. and methyl acrylate (147 g) was added. With vigorous stirring, Cu2 O (1 g) was added in small portions, whereupon an exothermic reaction took place to liberate a nitrogen gas. After the evolution of nitrogen gas had subsided, the reaction mixture was further stirred for 2 hours and, then, concentrated. The residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and the solvent was distilled off to give methyl 2-bromo-3-(4-cyclohexylphenyl)propionate as a crude oil (91 g, yield 98percent). NMR (delta ppm, CDCl3): 1.2-2.0 (10H, m), 2.5 (1H, m), 3.15 (1H, d.d, J=14 and 7 Hz), 3.43 (1H, d.d, J=14 and 7 Hz), 3.70 (3H, s), 4.37 (1H, t, J=7 Hz), 7.10 (4H, s).

Reference： [1]Patent: US5071841,1991,A

34
[ 6373-50-8 ]
[ 503832-22-2 ]

Yield	Reaction Conditions	Operation in experiment
47%	In N-(6,7-dibutoxy-4-methyl-2-quinazolinyl)guanidine;	EXAMPLE 36 N-(6-cyclohexyl-4-methyl-2-quinazolinyl)guanidine was made in the same manner as N-(6,7-dibutoxy-4-methyl-2-quinazolinyl)guanidine (see Example 1) except that <strong>[6373-50-8]4-cyclohexylaniline</strong> was used in place of 3,4-dibutoxyaniline. Name: 6-cyclohexyl-2,2,4-trimethyl-1,2-dihydroquinoline. (synthesised using Method B (47percent yield). Data: 1H NMR (CDCl3) delta 7.00 (d, 1H, J=1.8 Hz), 6.94 (dd, 1H, J=8.1, 1.8 Hz), 6.45 (3, 1H, J=8.1 Hz), 5.38 (d, 1H, J=1.2 Hz), 2.55-2.42 (m 1H), 2.09 (s, 3H), 1.97-1.91 (m, 5H), 1.83 (br d, 1H, J=12 Hz), 1.55-1.42 (m, 4H), 1.34 (s, 6H).

Reference： [1]Patent: US2003/176314,2003,A1

35
[ 6373-50-8 ]
[ 102928-38-1 ]
[ 927672-64-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 24h;Heating / reflux;	5.55.1 3-(4-Cyclohexylphenylamino)phthalic acid dimethyl ester A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.54 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.90 g of the product at 90:10 hexanes-ethyl acetate, in 78percent yield: 1H NMR (CDCl3) delta 1.27-1.44 (m, 6H), 1.73-1.85 (m, 4H), 2.45-2.55 (m, 1H), 3.86 (s, 3H), 3.88 (s, 3H), 7.00-7.10 (m, 3H), 7.15-7.18 (m, 2H), 7.23-7.34 (m, 2H), 8.07 (br, 1H).

Reference： [1]Patent: US2007/49618,2007,A1 .Location in patent: Page/Page column 78

36
5-(2-aminoquinazolin-6-yl)-2-fluorobenzoic acid [ No CAS ]
[ 6373-50-8 ]
'5-(2-amino-6-quinazolinyl)-N-(4-cyclohexylphenyl)-2-fluorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-[bis(dimethylamino)methylen]-1-H-benzotriazolim-tetrafluoroborate-3-oxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	<strong>[6373-50-8]4-cyclohexylbenzenamine</strong> (0.034 g, 0.194 mmol) was added to 5-(2-aminoquinazolin-6-yl)-2-fluorobenzoic acid (0.050 g, 0.177 mmol) in DMF (1 ml). TBTU (0.068 g, 0.212 mmol) was added, followed by DIPEA (0.045 g, 0.353 mmol). The mixture was stirred at RT overnight and then diluted with sodium bicarbonate and extracted (3.x.50 ml) with diethyl ether. The organic layer was washed with water (3.x.50 ml), dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica, eluting with 20percent MeOH/EtOAc, to afford the title compound as a pale yellow solid. MS m/z=441 [M+H]+; Calc'd for C27H25FN4O: 440

Reference： [1]Patent: US2007/54916,2007,A1 .Location in patent: Page/Page column 186

37
[ 938433-81-9 ]
[ 6373-50-8 ]
[ 936839-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); CyJohnPhos; In toluene; at 100℃; for 0.5h;Microwave irradiation;	Preparation of 1-[3-(4-cyclohexylphenylamino)pyrido[2,3-b]pyrazin-6-yl]-3-ethylurea (Reaction According to Scheme 3) 83 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.33 mmol), 99 mg of <strong>[6373-50-8]4-cyclohexylaniline</strong> (0.55 mmol), 30 mg of sodium tert-butoxide (0.30 mmol), 29 mg of tris(dibenzylideneacetone)dipalladium(0) (0.03 mmol) and 68 mg of 2-(dicyclohexylphosphanyl)biphenyl (0.19 mmol) were initially charged in 1.5 ml of dried toluene. The reaction mixture was heated to 100° C. under nitrogen in a microwave (100 watt) for 30 minutes. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid. m.p.: 246-248° C. ESI-MS: found m/z=391.3 (M+H+); calc. 390 amu 1H NMR (d6-DMSO): delta=1.18 (t, 3H), 1.22-1.26 (m, 1H), 1.33-1.44 (m, 4H), 1.71 (d, 1H), 1.80 (d, 4H), 2.45-2.51 (m, 1H), 3.25-3.30 (m, 2H), 7.22 (d, 2H), 7.40 (d, 1H), 7.89 (d, 2H), 8.08 (d, 1H), 8.37 (s, 1H), 8.73 (bs, 1H), 9.87 (s, 1H), 10.06 (s, 1H) ppm.

Reference： [1]Patent: US2007/149484,2007,A1 .Location in patent: Page/Page column 110

38
[ 6373-50-8 ]
[ 37772-85-3 ]
[ 1005179-35-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1840 - 1844

39
[ 6373-50-8 ]
[ 6283-74-5 ]
[ 1013332-97-2 ]

Yield	Reaction Conditions	Operation in experiment
~ 100%	With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 20℃; for 3h;	216 mg of (+)-diacetyl-L-tartaric anhydride (1 mmol) and 263 mg of 4-cyclohexyl-phenylamine (1.5 mmol) and 200 mul of N-methylmorpholine were dissolved in 5 ml of DMF and the mixture was stirred for 3 h at RT. The mixture was diluted with ethyl acetate. The organic phase was washed with 1 N HCl solution and common salt solution, dried over sodium sulfate, filtered and the solvents were removed under reduced pressure. 430 mg of the title compound were obtained as an oil (Yield approximately 100percent). LC/MS (Method D) (M+H)+ 392

Reference： [1]Patent: US2009/233961,2009,A1 .Location in patent: Page/Page column 10

40
[ 6373-50-8 ]
[ 762-42-5 ]
[ 1169879-62-2 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 4572 - 4576
Angew. Chem., Int. Ed.,2009,vol. 121,p. 4642 - 4646

41
[ 1005333-37-8 ]
[ 6373-50-8 ]
[ 1005333-39-0 ]

Yield	Reaction Conditions	Operation in experiment
29%	In tetrahydrofuran; at 100℃; for 0.0833333h;Microwave irradiation;	C. tert-Butyl-3-[(N-(4-cyclohexylphenyl)amino)carbonyl]-4-hydroxy-2-oxo-1,5,7,8-tetrahydro-1,6-naphthyridine-6(2H)-carboxylate (43a2 b1) To a solution of 42a2 (144.7 mg, 0.44 mmol) in THF (2 mL) was added 4-cyclohexyl aniline (85.4 mg, 0.48 mmol). The reaction mixture was heated at 100° C. in a microwave synthesizer for 5 minutes. The suspension was filtered and the solid was rinsed with cold isopropanol to afford the title compound as a white solid (60 mg, 29percent). MS (ES+): m/z=468 (M+1) 1H NMR (600 MHz, DMSO-D6) delta=1.22 (d, J=11.62 Hz, 2H) 1.33-1.43 (m, 13H) 1.70 (d, J=11.62 Hz, 2H) 1.78 (d, J=9.09 Hz, 4H) 3.56 (d, J=12.09 Hz, 2H) 3.68 (s, 1H) 3.94 (s, 1H) 7.21 (s, 2H), 7.75 (s, 2H)

Reference： [1]Patent: US2009/325948,2009,A1 .Location in patent: Page/Page column 100

42
[ 1005333-34-5 ]
[ 6373-50-8 ]
[ 1005333-38-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	In N,N-dimethyl-formamide; at 150℃; for 0.166667h;Microwave irradiation;	B. tert-Butyl 3-[(N-(4-cyclohexylphenyl)amino)carbonyl]-4-hydroxy-2-oxo-1,5,7,8-tetrahydro-1,6-naphthyridine-6(2H)-carboxylate (43a1 b1) To a solution of 42a1 (75 mg, 0.22 mmol) in DMF (1.5 mL) was added <strong>[6373-50-8]4-cyclohexylaniline</strong> (38.5 mg, 0.22 mmol) and the resulting mixture was heated in a microwave synthesizer at 150° C. for 10 min. The suspension was filtered and the solid was rinsed with cold methanol to afford the title compound as a white solid (70 mg, 65percent). MS (ES+): m/z=468 (M+1) 1H NMR (600 MHz, DMSO-D6) delta=1.24 (m, 1H) 1.34 (m, 2H) 1.38 (m, 2H) 1.43 (s, 9H) 1.70 (d, J=12.00 Hz, 1H) 1.78 (d, J=6.00 Hz, 4H) 2.62 (s, 2H) 3.58 (s, 2H) 4.20 (s, 2H) 7.23 (d, J=7.37 Hz, 2H) 7.51 (d, J=7.55 Hz, 2H) 11.99 (s, 1H) 12.45 (s, 1H) 15.71 (s, 1H)

Reference： [1]Patent: US2009/325948,2009,A1 .Location in patent: Page/Page column 100

43
6-tert-butyl 3-methyl 4-hydroxy-2-oxo-1,2,4a(R),5,7,7a(S)-hexahydro-6H-pyrrolo[3,4-b]pyridine-3,6-dicarboxylate [ No CAS ]
[ 6373-50-8 ]
tert-butyl 3-[(4-cyclohexylphenyl)aminocarbonyl]-4-hydroxy-2-oxo-1,2,4a(R),5,7,7a(S)-hexahydro-1H-pyrrolo[3,4-b]pyridine-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	In tetrahydrofuran; at 100℃; for 0.166667h;Microwave irradiation;	B. Trans-butyl-3[(N-(4-cyclohexyl-phenyl)-amino)carbonyl]-4-hydroxy-2-oxo-2,4-a,5,6,7,7a-hexahydro-1H-pyrrolo[3,4-b]pyridine-3-carboxamide (48a2b1) To a solution of 47a2 (150 mg, 0.46 mmol) in THF (2 mL) was added 4-cyclohexyl aniline (80 mg, 0.46 mmol) and the resulting mixture was heated in a microwave synthesizer at 100° C. for 10 min, then concentrated in vacuo. The crude product was purified by silica gel chromatography, eluding with 20percent EtOAc in hexane. Fractions containing the desired product were concentrated to afford the title compound as a white solid (100 mg, 46percent) MS (ES+): m/z 456 (M+1) 1H NMR (400 MHz, DMSO-D6) delta=1.18-1.27 (m, 2H) 1.30-1.39 (m, 3H) 1.40 (s, 9H) 1.70 (d, J=12.13 Hz, 2H) 1.78 (d, J=9.60 Hz, 5H) 3.08-3.13 (m, 1H) 3.45-3.73 (m, 3H) 4.12-4.26 (m, 1H) 7.19-7.24 (m, 2H) 7.39-7.45 (m, 2H)

Reference： [1]Patent: US2009/325948,2009,A1 .Location in patent: Page/Page column 103

44
[ 75-77-4 ]
[ 6373-50-8 ]
C₁₅H₂₅NSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (5 g, 28.6 mmol) in 75 ml of dry THF at -70 to -75° C. was added slowly by syringe a solution of 17.7 ml of 1.6 M n-butyllithium. When addition was complete, the resulting mixture was stirred at -70 to -75° C. for 0.5 h. To the stirred mixture was then added 3.61 ml (28.5 mmol) of chlorotrimethylsilane at -70 to -75° C. The mixture was then allowed to warm to RT and stirred at RT for 1.75 h. The mixture was then again cooled to -70 to -75° C. after which was slowly added 17.5 ml of 1.6 M n-butyllithium in hexanes. The mixture was allowed to stir at -70 to -75° C. for 0.5 h after which was added 2.45 ml (28.6 mmol) of epibromohydrin. The mixture was allowed to warm to room temperature and stirred for 2 h at room temperature. The mixture was then poured into 250 ml of cold saturated aqueous sodium bicarbonate, extracted with ethyl acetate, washed with brine, dried (sodium sulfate) and concentrated to provide an orange oil which was then purified by chromatography on silica gel, eluding with ethyl acetate/heptane to provide 3.06 g of the title compound. 1H NMR (CDCl3, 300 MHz), delta 7.04 (d, 2H), 6.60 (d, 2H), 3.76 (br s, 1H), 3.44-3.56 (m, 1H), 3.14-3.27 (m, 2H), 2.80 (m, 1H), 2.68s (m, 1H), 2.37 (br s, 1H), 1.66-1.96 (m, 5H), 1.09-1.66 (m, 5H).

Reference： [1]Patent: US2010/75994,2010,A1 .Location in patent: Page/Page column 70

45
[ 6373-50-8 ]
[ 123-54-6 ]
[ 1238700-97-4 ]

Yield	Reaction Conditions	Operation in experiment
51%		Reference Example 643-[(4-Cyclohexylphenyl)hydrazono]pentane-2,4-dione To a solution of <strong>[6373-50-8]4-cyclohexylaniline</strong> (500 mg, 2.86 mmol) in 10 mL of acetic acid and 2 mL of concentrated hydrochloride solution, sodium nitrite (237 mg, 3.43 mmol) in 4 mL of water was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (703 mg, 8.58 mmol) and acetylacetone (372 mg, 3.72 mmol) in 10 mL of ethanol and 6 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water,EtOH/H2O (1:1) and hexane, and dried to give 3-[(4-cyclohexylphenyl)hydrazono]pentane-2,4-dione (420 mg, 51percent).1H NMR (400 MHz, CDCl3): delta ppm 1.24-1.27 (m, 2H), 1.38-1.43 (m, 4H), 1.85-1.87 (m, 4H), 2.49-2.52 (m, 4H), 2.60 (s, 3H), 7.25 (d, J=8.4 Hz, 2H), 7.35 (d, J=8.8 Hz, 2H), 14.81 (s, 1H).

Reference： [1]Patent: US2010/197651,2010,A1 .Location in patent: Page/Page column 56

46
[ 6373-50-8 ]
[ 1246760-10-0 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 6174 - 6177

47
[ 6373-50-8 ]
4-(2-oxoimidazolidin-1-yl)benzene-1-sulfonyl chloride [ No CAS ]
[ 1328951-74-1 ]

Yield	Reaction Conditions	Operation in experiment
35%	With dmap; In acetonitrile; at 25℃;Inert atmosphere;	General procedure: Compound 51 (1.00 mmol) was suspended in dry acetonitrile (10 mL) under nitrogen atmosphere. Relevant aniline (1.00 mmol) and 4-dimethylaminopyridine (4.00 mmol) were successively added dropwise and the mixture was stirred at room temperature for 48 h. Ethyl acetate was added and the solution was washed with hydrochloric acid 1N, brine, dried over sodium sulfate, filtered, and evaporated to dryness under vacuum. The white solid was purified by flash chromatography on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5327 - 5342

48
[ 121032-11-9 ]
[ 6373-50-8 ]
[ 1381761-42-7 ]

Yield	Reaction Conditions	Operation in experiment
65.4%		Step 1. To a solution of triphosgene (62.8 mg, 0.21 mmol) in 10 mL of dry DCM at 0° C was stirred, a solution of <strong>[6373-50-8]4-cyclohexylbenzenamine</strong> (91 mg, 0.52 mmol) and TEA (105.0 mg, 1.0 mmol) was added dropwise. The reaction mixture was stirred for 5 min at 0° C and the resulting solution of isocyanate was added slowly to a solution N1- (((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][l,3]dioxol- 4-yl)methyl)-Nl-methylpropane-l,3-diamine (100 mg, 0.26 mmol) at room temperature and was stirred for 2h. The reaction was quenched with H20, extracted with DCM (10 mL x 3), washed with brine (10 mL), dried and concentrated to the crude. The crude was purified by SGC (DCM : MeOH =10 : 1) to obtain 184 (100 mg, Yield: 65.4percent ) LC-MS (m/z): 579.3 [M+l]+.

Reference： [1]Patent: WO2012/82436,2012,A2 .Location in patent: Page/Page column 144-145

49
[ 6373-50-8 ]
[ 77846-07-2 ]
[ 1421739-79-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With N-ethyl-N,N-diisopropylamine; In dichloromethane;Inert atmosphere; Cooling with ice;	General procedure: 2-[(Benzyloxy)imino]acetylchloride (8) (0.89 g, 4.55 mmole) was dissolved in DCM (20 ml) and added dropwise to an ice bath cooled solution of the 2,4-dimethylaniline (0.524 g, 4.32 mmole, 0.54 ml, 0.95 eq.) in DCM (30 ml) and N,N-diisopropylethylamine (0.95ml, 5.5 mmole, 1.2 eq.). On completion of the addition, the cold bath was removed, and the reaction mixture was allowed to warm to room temperature. The crude product was partitioned between 1percent HCl and DCM. The organic phase was separated, washed with brine, dried over Na2SO4, and the solvents were evaporated. The resulting tan solid was triturated with 10percent ether in hexane, filtered, rinsed with cold solvent mixture, and dried under vacuum to yield 0.96 g (3.40 mmole, 75percent) of the title compound as an off-white solid.#10;#10;

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1008 - 1011

50
[ 924-44-7 ]
[ 600-22-6 ]
[ 6373-50-8 ]
[ 1494412-83-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With iron(III) chloride; In acetonitrile; at 20℃; for 30h;	General procedure: The reaction mixture of arylamine 1 (0.5mmol), ethyl glyoxylate 2 (0.55mmol), alpha-ketoesters 3 (0.75mmol), FeCl3 (5molpercent) and CH3CN (3mL) was stirred at room temperature or 60°C for the indicated time until complete consumption of the starting material, which was monitored by TLC analysis (30?36h). Then the solvents were removed by rotary evaporation to provide crude products. The residue was purified by flash chromatography on silica gel to give the desired product 4. Compound 4f was obtained in 71percent yield according to the general procedure (rt, 30h). TLC (n-hexane/EtOAc, 3:1 v/v): Rf=0.50; 1H NMR (600MHz, CDCl3): delta=1.27?1.33 (m, 1H), 1.42?1.46 (m, 2H), 1.48 (t, J=7.1Hz, 3H), 1.51?1.58 (m, 2H), 1.78 (d, J=12.8Hz, 1H), 1.89 (d, J=12.9Hz, 2H), 1.97 (d, J=12.0Hz, 2H), 2.74?2.78 (m, 1H), 4.06 (s, 3H), 4.56 (q, J=7.1Hz, 2H), 7.72 (dd, J=1.6, 8.8Hz, 1H), 8.27 (d, J=8.8Hz, 1H), 8.62 (s, 1H), 8.63 (s, 1H); 13C NMR (150MHz, CDCl3): delta=14.4, 26.0, 26.7, 34.1, 45.1, 52.8, 62.4, 122.1, 122.3, 126.5, 130.8, 131.1, 135.2, 146.9, 147.8, 150.7, 165.0, 166.3; HRMS calcd for C20H23NO4Na (M+Na)+, 364.1519; found, 364.1518.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10747 - 10751

51
[ 737760-32-6 ]
[ 6373-50-8 ]
C₃₉H₅₄N₆O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-(4, 6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride n-hydrate; In water; isopropyl alcohol; at 20℃; for 6h;	General procedure: To a solution of 2 (a salt oftriethylamine, 34.8 g, 45.9mmol) in 2-propanolwater (19:1, 700 ml),4-butylaniline (7.03 g, 47.1mmol) and 4-(4, 6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride n-hydrate (DMT-MM) (20.0 g, approximately70mmol) were added and the mixture was stirred for 6 h at roomtemperature. Concentration gave a residue, which was dissolved in 5percent aqueouspotassium hydrogen sulfate (800 ml). The aqueous solution was washed withEtOAc and neutralized with 10percent aqueous sodium carbonate (300 ml). Theprecipitate obtained was extracted with EtOAc. The organic solution waswashed with saturated aqueous sodium chloride, dried (Na2SO4) andconcentrated to afford 500-N-Boc protected intermediate of 4b (32.2 g, 92percentfrom caprazene) as a pale-yellow solid. This solid was used in the next reactionwithout further purification.

Reference： [1]Journal of Antibiotics,2013,vol. 66,p. 171 - 178

52
[ 58757-38-3 ]
[ 6373-50-8 ]
6-chloro-N-(4-cyclohexylphenyl)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In toluene; at 0 - 20℃; for 1h;	6-Chloronicotinoyl chloride (0.24 g) was dissolved in toluene (5 mL), and the solution was cooled to 0° C. <strong>[6373-50-8]4-Cyclohexylaniline</strong> (0.47 g) was added thereto at 0° C., and the mixture was stirred at room temperature for 1 hour. Ethyl acetate was added thereto, and the organic layer was washed with a 1 N aqueous sodium hydroxide solution and water and dried over sodium sulfate. After concentration under reduced pressure, the obtained solid was collected by filtration and washed with diethyl ether. The solid was dried under reduced pressure to obtain the title compound (0.40 g) as a white solid (yield: 95percent). [0259] 1H-NMR (500 MHz, CDC3) delta: 8.85 (1H, d, J=2 Hz), 8.17 (1H, dd, J=8 Hz, 2 Hz), 7.68 (1H, brs), 7.52 (2H, d, J=9 Hz), 7.47 (1H, d, J=8 Hz), 7.24 (2H, d, J=9 Hz), 2.56-2.46 (1H, m), 1.92-1.80 (4H, m), 1.80-1.71 (1H, m), 1.46-1.36 (4H, m), 1.33-1.20 (1H, m).

Reference： [1]Patent: US2015/11552,2015,A1 .Location in patent: Paragraph 0257-0258

53
[ 6373-50-8 ]
[ 90-02-8 ]
2-(((4-cyclohexylphenyl)amino)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Under an atmosphere of N2, 0.175 g (1 mmol) compd. 2 was dissolved in methanol, 0.11 mL (1.05 mmol) salicylaldehyde was added and stirred overnight at room temperature. When compd. 2 disappeared, NaBH4 (61 mg, 1.6 mmol) was added. After stirring for 10 min, the reaction was quenched by sat. NH4Cl solution, then extracted with CH2Cl2 (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE:EtOAc = 15:1) to afford 0.230 g (82percent) E6 as white solid: m.p. 105-106°C; IR(neat) v= 3284, 3259, 2918, 2848, 1614, 1593, 1515, 1456, 1249, 821, 750 cm-1; 1H NMR (400 MHz, CDCl3) delta 8.73 (brs, 1H), 7.22 (t, J = 8.2 Hz, 1H), 7.14 (d, J = 7.5 Hz, 1H), 7.10 (d, J = 8.4 Hz, 2H), 6.87 (m, 2H), 6.80 (d, J= 8.4 Hz, 2H), 4.41 (s, 2H), 3.86 (brs, 1H), 2.43 (s, 1H), 1.83 (s, 4H), 1.73 (d, J = 11.4 Hz, 1H), 1.36 (t, J = 9.6 Hz, 4H), 1.26 (m, 1H); 13C NMR (101 MHz, CDCl3) delta 157.04, 144.97, 141.03, 129.19, 128.63,127.67, 122.97, 119.94, 116.68, 116.17, 49.33, 43.77, 34.66, 26.94, 26.17; LRESI-MS m/z: 176.1, 282[M+H]+; HRMS (ESI) calcd. for C19H23NO [M+H]+281.1780, found 282.1859; Elemental Analysis: calcd(percent) C 81.80, H 8.24, N 4.98; found C 81.11, H 8.43, N 5.02.