[ CAS No. 1711-11-1 ] {[proInfo.proName]}

Name: 1711-11-1|3-Cyanobenzoyl chloride|95%
Brand: Ambeed
SKU: A470238
Price: 17.0 USD
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Quality Control of [ 1711-11-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1711-11-1 ]

Product Details of [ 1711-11-1 ]

CAS No. :	1711-11-1	MDL No. :	MFCD00011545
Formula :	C₈H₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RPESZQVUWMFBEO-UHFFFAOYSA-N
M.W :	165.58	Pubchem ID :	308483
Synonyms :

Calculated chemistry of [ 1711-11-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.34
TPSA :	40.86 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	2.46
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	2.3
Consensus Log Po/w :	1.94

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.75
Solubility :	0.292 mg/ml ; 0.00176 mol/l
Class :	Soluble
Log S (Ali) :	-2.96
Solubility :	0.181 mg/ml ; 0.00109 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.04
Solubility :	0.151 mg/ml ; 0.000912 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 1711-11-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H302+H312+H332-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1711-11-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1711-11-1 ]
Downstream synthetic route of [ 1711-11-1 ]

[ 1711-11-1 ] Synthesis Path-Upstream 1~5

1
[ 1877-72-1 ]
[ 6068-72-0 ]
[ 1711-11-1 ]

Reference： [1] Patent: US6433211, 2002, B1,

2
[ 1877-72-1 ]
[ 1711-11-1 ]

Reference： [1] Chemische Berichte, 1938, vol. 71, p. 335,338
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1230 - 1241
[3] Journal of Medicinal Chemistry, 1982, vol. 25, # 2, p. 145 - 152
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 366 - 370
[5] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211
[6] European Journal of Medicinal Chemistry, 1994, vol. 29, # 11, p. 841 - 854
[7] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
[8] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410
[9] Journal of the Chemical Society. Perkin Transactions 2, 1997, # 8, p. 1493 - 1497
[10] Pesticide Science, 1994, vol. 41, # 2, p. 139 - 148
[11] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 16, p. 3379 - 3392
[12] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 4, p. 1305 - 1323
[13] Archiv der Pharmazie, 2006, vol. 339, # 3, p. 115 - 122
[14] Chemistry - A European Journal, 2005, vol. 11, # 19, p. 5674 - 5688
[15] Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1706 - 1714
[16] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2430 - 2433
[17] Patent: EP1195372, 2002, A1, . Location in patent: Page 52
[18] Patent: US5958944, 1999, A,
[19] Patent: US6121301, 2000, A,
[20] Patent: US6121301, 2000, A,
[21] Patent: US4853398, 1989, A,
[22] Russian Chemical Bulletin, 2007, vol. 56, # 6, p. 1216 - 1226
[23] Patent: EP1348706, 2003, A1, . Location in patent: Page/Page column 54-55
[24] Patent: WO2009/144115, 2009, A1, . Location in patent: Page/Page column 39
[25] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 6, p. 481 - 484
[26] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 231 - 243
[27] ChemMedChem, 2012, vol. 7, # 10, p. 1825 - 1839
[28] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 22, p. 6974 - 6979,6
[29] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6761 - 6774
[30] MedChemComm, 2013, vol. 4, # 11, p. 1443 - 1451
[31] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194
[32] Organic Letters, 2014, vol. 16, # 2, p. 390 - 393
[33] Journal of the American Chemical Society, 2014, vol. 136, # 41, p. 14349 - 14352
[34] Chemistry - A European Journal, 2016, vol. 22, # 4, p. 1362 - 1367
[35] Patent: US2016/46597, 2016, A1, . Location in patent: Paragraph 0184
[36] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277
[37] Tetrahedron, 2017, vol. 73, # 12, p. 1576 - 1582

3
[ 1877-72-1 ]
[ 107-06-2 ]
[ 1711-11-1 ]

Reference： [1] Patent: US6433211, 2002, B1,

4
[ 1877-72-1 ]
[ 6068-72-0 ]
[ 1711-11-1 ]

Reference： [1] Patent: US6433211, 2002, B1,

5
[ 79-37-8 ]
[ 1877-72-1 ]
[ 1711-11-1 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 24, p. 3097 - 3101

[ 1711-11-1 ] Synthesis Path-Downstream 1~65

1
[ 1877-72-1 ]
[ 1711-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In N-methyl-acetamide; dichloromethane;	(a) Thionyl chloride (10 ml) and dimethylformamide (1 drop) were added to a solution of 3-cyanobenzoic acid (10 g) in dichloromethane (100 ml), and the mixture was refluxed far 3 hours. After the reaction, the solvent was evaporated under reduced pressure to give 3-cyanobenzoyl chloride.
	With thionyl chloride; In hexane; N,N-dimethyl-formamide; toluene;	Referential Example 1 2-[N-(3-Cyanobenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole STR6 Step 1 In 10 ml of toluene, 576 mg of 3-cyanobenzoic acid were suspended, followed by the addition of 699 mg of thionyl chloride and 0.5 ml of N,N-dimethylformamide. The resulting mixture was stirred under heating at 80 C. for 5 hours. After cooling, the solvent was distilled off from the reaction mixture under reduced pressure. To the residue, n-hexane was added. The solvent was then distilled off, whereby 3-cyanobenzoyl chloride was obtained.
	With thionyl chloride; In hexane; N,N-dimethyl-formamide; toluene;	Example 1 2-[N-(3-Cyanobenzoyl)amino]-4-[(2-diisopropylaminoethyl)aminocarbonyl]-1,3-thiazolehydrochloride STR7 Step 1 In 1 liter of toluene, 200 g of 3-cyanobenzoic acid were suspended, followed by the addition of 128 ml of thionyl chloride and 1 ml of N,N-dimethylformamide. The resulting mixture was stirred under heating at 80 C. for 5 hours. After cooling of the reaction mixture, the solvent was distilled off under reduced pressure. To the residue, n-hexane was added. By distilling off the solvent under reduced pressure, 3-cyanobenzoyl chloride was obtained.

	With thionyl chloride; In dichloromethane;	A. Preparation of 3-cyanobenzoyl chloride A mixture of 50 g. of 3-cyanobenzoic acid and 100 ml. of thionyl chloride were stirred overnight in 500 ml. of methylene chloride. The solvent and excess thionyl chloride were removed in vacuo providing 55.3 g. of crude subtitle intermediate which was used without further purification. Analysis for C8 H4 ClNO: Calculated: C, 58.03; H, 2.44; N, 8.46; Found: C, 58.24; H, 2.61; N, 8.26.
	With thionyl chloride;N,N-dimethyl-formamide; In tetrahydrofuran; at 60℃; for 2h;	<strong>[1877-72-1]3-Cyanobenzoic acid</strong> (12.60 g) was dissolved in THF (200 ml) and thionyl chloride (13.0 g) and DMF (0.05 ml) were added. The mixture was stirred at 60§C for 2 hrs. The reaction mixture was concentrated under reduced pressure and re-dissolved in THF (100 ml). The solution was slowly added to 50% aqueous dimethylamine solution (80 ml) cooled to 5§C. The reaction mixture was stirred at room temperature for one hr. and extracted with ethyl acetate. The extract was dried and concentrated, and the residue was recrystallized from hexane-diisopropyl ether to give the title compound (8.00 g) as colorless powder crystals. 1H-NMR (CDCl3) delta: 2.99 (3H, s), 3.13 (3H, s), 7.55 (1H, t, J=8.1 Hz), 7.64 - 7.74 (3H, m). IR (KBr): 3054, 2228, 1613, 1580 cm-1.
	With thionyl chloride; In toluene; at 50 - 95℃; for 20.5h;Inert atmosphere;	150 g of 3-cyanobenzoic acid are first introduced into 1000 ml of dry toluene under inert gas and heated to 500C, with stirring. To the resulting white suspension there are added, dropwise, 96 ml of thionyl chloride over a period of 150 minutes, the temperature being gradually increased to 95C. Stirring is then carried out for a further 18 hours at 900C. The resulting brown solution is heated to reflux, and about 200 ml of a clear solution are distilled off under a gentle current of nitrogen. Cooling to 900C again is then carried out, and 106 g of 3- dimethylamino-1 -propylamine are then added dropwise over 75 minutes, with stirring. Stirring is subsequently carried out for a further 120 minutes whilst refluxing gently (about 100C). To the cooled reaction mixture there are added 500 ml of ethyl acetate and 500 ml of 2N sodium hydroxide solution and extraction is carried out. The aqueous phase is extracted a further three times using 300 ml of ethyl acetate each time; 60 ml of 30 % sodium hydroxide solution are added and extraction is carried out a further three times using 300 ml of ethyl acetate each time. The combined organic extracts are washed with 500 ml of saturated NaCI solution, dried over sodium sulfate and activated carbon and concentrated at 50C using a rotary evaporator. Addition of 200 ml of methylene chloride to the residue and concentration are carried out a further three times. There are obtained 212.1 g of a clear brown oil of formula 1H NMR (300 MHz, CDCI3): 9.03 (1 H, broad m, N-H); 8.04 (1 H, t, 1.4 Hz); 8.00 (1 H, dt, 7.8 and 1.4 Hz); 7.74 (1 H, dt, 7.8 and 1.4 Hz); 7.54 (1 H, t, 7.8 Hz); 3.55 (2H, dt, 6.0 and 4.7 Hz); 2.53 (2H, t, 5.8 Hz); 2.31 (6H, s); 1.77 (2H, m).
	With thionyl chloride; for 2h;Heating;	A mixture of 2-chlorobenzoic acid (1b) (0.61 g, 3.92 mmol) and thionyl chloride (1 mL) was heated for 2 h. The excess of thionyl chloride was recovered under reduced pressure and the residue so obtained was dissolved in dry dioxane (1 mL). The solution was then dropwise added to mixture of 2-amino-4,5-dimethoxybenzamide (2) (0.7 g, 3.57 mmol) and TEA (1.2 mL, 8.92 mmol) in dry dioxane (2 mL) at 10 C. The reaction mixture was stirred at rt for another 1 h and quenched into cold water (50 mL). The precipitate formed was filtered, washed with water and dried to obtain compound 3b (0.85 g, 71%): mp 213-215 C (dec.); IR (KBr,): 3406, 3305, 1658, 1645, 1612, 1525, 1253, 1078 and 1039 cm-1.
	With thionyl chloride; for 5h;Reflux;	General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C.
	With thionyl chloride; N,N-dimethyl-formamide; In N,N-dimethyl-formamide; toluene; at 95℃; for 4h;	To a solution of 3-cyanobenzoic acid (7 g, 47.61 mmol) in toluene (100 mL) was added SOCl2 (17.38 mL, 238.09 mmol) and DMF (2-3 drops, catalytic). The reaction mixture was allowed to heat at 95 C. for 4 h. The progress of reaction was monitored by TLC (30% Ethyl acetate in hexane, the reaction mass was quenched with dry methanol for TLC). After completion, reaction mixture was concentrated in vacuo to give a crude 3-cyanobenzoyl chloride (7.84 g, 99%) which is used in the next reaction without further purification.
	With thionyl chloride; In toluene; for 2h;Reflux;	General procedure: To the carboxylic acid (4.98 mmol), PhMe (25 mL) was added followed by SOCl2 (1.1 mL, 14.92 mmol). The suspension was heated to reflux for 2 h before the solvent was removed under reduced pressure. The mixture was dissolved in dry DCM (10 mL) before K2CO3 (1.5 g, 10.85 mmol) was added and morpholine amine (1.5 mL) was added drop wise at 0 C. The cooling bath was removed after 30 min and stirring was continued at rt overnight. The mixture was filtered, the solvent evaporated and the crude material was purified by column chromatography.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2h;	General procedure: One drop of dry N,N-dimethyl formamide and oxalyl chloride (0.62 g, 4.9 mmol) were addeddropwise to a solution of 4-methoxybenzoic acid (0.50 g, 3.3 mmol) in dry CH2Cl2 (20 mL). The reactionmixture was stirred at room temperature for 2 h, and then distilled in vacuo to give the crude acylchloride, which was dissolved in dry CH2Cl2 (10 mL). Dry triethylamine (0.40 g, 3.9 mmol) was addedto a solution of benzylamine (0.35 g, 3.3 mmol) in dry CH2Cl2 (20 mL). The reaction mixture wascooled to 0 C, and the acyl chloride solution was added dropwise. After stirring at 20-25 C for 4 h,the reaction mixture was distilled in vacuo, and washed with a 10% solution of NaOH and water,and dried. Silica gel column chromatography (hexane/ethyl acetate) afforded I-1 as a white powder(0.75 g, 94.8% yield).

Reference： [1]Chemische Berichte,1938,vol. 71,p. 335,338
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 1230 - 1241
[3]Journal of Medicinal Chemistry,1982,vol. 25,p. 145 - 152
[4]Journal of Medicinal Chemistry,1981,vol. 24,p. 366 - 370
[5]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 202 - 211
[6]European Journal of Medicinal Chemistry,1994,vol. 29,p. 841 - 854
[7]Journal of Medicinal Chemistry,1995,vol. 38,p. 3094 - 3105
[8]Journal of Medicinal Chemistry,1998,vol. 41,p. 2390 - 2410
[9]Journal of the Chemical Society. Perkin Transactions 2 (2001),1997,p. 1493 - 1497
[10]Pesticide Science,1994,vol. 41,p. 139 - 148
[11]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 3379 - 3392
[12]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1305 - 1323
[13]Archiv der Pharmazie,2006,vol. 339,p. 115 - 122
[14]Chemistry - A European Journal,2005,vol. 11,p. 5674 - 5688
[15]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1706 - 1714
[16]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2430 - 2433
[17]Patent: EP1195372,2002,A1 .Location in patent: Page 52
[18]Patent: US5958944,1999,A
[19]Patent: US6121301,2000,A
[20]Patent: US6121301,2000,A
[21]Patent: US4853398,1989,A
[22]Russian Chemical Bulletin,2007,vol. 56,p. 1216 - 1226
[23]Patent: EP1348706,2003,A1 .Location in patent: Page/Page column 54-55
[24]Patent: WO2009/144115,2009,A1 .Location in patent: Page/Page column 39
[25]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 481 - 484
[26]European Journal of Medicinal Chemistry,2012,vol. 48,p. 231 - 243
[27]ChemMedChem,2012,vol. 7,p. 1825 - 1839
[28]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6974 - 6979,6
[29]Journal of Medicinal Chemistry,2013,vol. 56,p. 6761 - 6774
[30]MedChemComm,2013,vol. 4,p. 1443 - 1451
[31]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 192 - 194
[32]Organic Letters,2014,vol. 16,p. 390 - 393
[33]Journal of the American Chemical Society,2014,vol. 136,p. 14349 - 14352
[34]Chemistry - A European Journal,2016,vol. 22,p. 1362 - 1367
[35]Patent: US2016/46597,2016,A1 .Location in patent: Paragraph 0184
[36]Journal of Materials Chemistry C,2016,vol. 4,p. 4269 - 4277
[37]Tetrahedron,2017,vol. 73,p. 1576 - 1582
[38]Angewandte Chemie - International Edition,2018,vol. 57,p. 15762 - 15766
Angew. Chem.,2018,vol. 130,p. 15988 - 15992,5
[39]Molecules,2019,vol. 24
[40]Organic Letters,2019,vol. 21,p. 2645 - 2649
[41]Angewandte Chemie - International Edition,2019,vol. 58,p. 9099 - 9103
Angew. Chem.,2019,vol. 131,p. 9197 - 9201,5
[42]ChemMedChem,2019,vol. 14,p. 1662 - 1668

2
[ 62-53-3 ]
[ 1711-11-1 ]
[ 143330-38-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In dichloromethane; water; at 20℃;	General procedure: All materials, reagents and solvents were purchased fromSigma-Aldrich, Merck, and Tedia Brazil and were used as received.The classical Schotten-Baumann reaction was used for the synthesisof amides [23-25]. Typical procedure: A solution of the acylchloride (0.5 mmol) in dichloromethane (2 mL) was added dropwiseto a well-stirred mixture of the aniline (0.5 mmol) indichloromethane (2 mL) and 2 mL of aqueous sodium carbonate(10%) at room temperature. The reaction media was stirred for90 min and then the organic phase was separated and extractedwith brine (3 x 2 mL). The combined organic fractions were dried over MgSO4, filtered, and evaporated to dryness under reducedpressure to give the N-phenylbenzamides in 19-90% yields. Onehundred and seventeen compounds were synthesized followingthis procedure. Detailed physicochemical properties, 1H and 13CNMR data, FT-IR data, and yield are presented for each N-phenylbenzamidein the supplementary data.

Reference： [1]Antimicrobial Agents and Chemotherapy,2014,vol. 58,p. 4242 - 4245
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 3633 - 3640
[3]Journal of Molecular Structure,2020,vol. 1208

3
[ 617-65-2 ]
[ 1711-11-1 ]
[ 104252-73-5 ]

Yield	Reaction Conditions	Operation in experiment
81.2%	With sodium hydroxide In water at 15 - 20℃; for 4h;

Reference： [1]Makovec; Chiste; Bani; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 1, p. 9 - 20]

4
[ 20059-73-8 ]
[ 1711-11-1 ]
[ 122893-03-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 202 - 211

5
[ 1711-11-1 ]
[ 617-45-8 ]
[ 104252-74-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 9 - 20

6
[ 1711-11-1 ]
[ 486-70-4 ]
3-Cyano-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

7
[ 67-56-1 ]
[ 1711-11-1 ]
[ 13531-48-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃;	General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5°C.

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2390 - 2410
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 192 - 194

8
[ 76918-64-4 ]
[ 1711-11-1 ]
[ 840531-23-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1305 - 1323

9
[ 108719-40-0 ]
[ 1711-11-1 ]
3-cyano-N-(1,4-diphenyl-1H-pyrazol-5-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;

Reference： [1]De Paulis, Tomas; Hemstapat, Kamondanai; Chen, Yelin; Zhang, Yongqin; Saleh, Samir; Alagille, David; Baldwin, Ronald M.; Tamagnan, Gilles D.; Conn, P. Jeffrey [Journal of Medicinal Chemistry, 2006, vol. 49, # 11, p. 3332 - 3344]

10
[ 41825-73-4 ]
[ 1711-11-1 ]
N-(2-bromo-4,6-dimethyl-phenyl)-3-cyanobenzamide [ No CAS ]
N-(2-bromo-4,6-dimethylphenyl)-3-cyano-N-(3-cyanobenzoyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 61% 2: 3.4%	With triethylamine In dichloromethane at 20℃;

Reference： [1]Patil, Shivaputra; Kamath, Shantaram; Sanchez, Tino; Neamati, Nouri; Schinazi, Raymond F.; Buolamwini, John K. [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 3, p. 1212 - 1228]

11
[ 1018975-59-1 ]
[ 1711-11-1 ]
1-[5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 150℃; for 0.5h;Microwave irradiation;	Example 2781-[5-(3-Cyanophenyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-4- (trif luoromethyl)-1 H-indole-5-carbonitrile; To a solution of (1Z)-2-[5-cyano-2-propyl-4-(trifluoromethyl)-1/-/-indol-1-yl]-Lambda/- hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol) in anhydrous acetonitrile (3.0 ml_) under N2, was added <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (0.204 g, 1.23 <n="260"/>mmol) and N,N-diisopropylethylamine (0.50 ml_, 5.21 mmol). The mixture was then heated in a microwave at 15O0C for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.079 g (59% yield) of pure product: MS (ES) m/z 435 (M+).

Reference： [1]Patent: WO2008/42571,2008,A2 .Location in patent: Page/Page column 258-259

12
[ 1711-11-1 ]
[ 74-89-5 ]
[ 363186-09-8 ]

Yield	Reaction Conditions	Operation in experiment
895 mg	In tetrahydrofuran; water for 18h;
	In tetrahydrofuran; water at 5℃; for 1h;	26.i i) Production of 3-cyano-N-methylbenzamide A mixture of 40% aqueous methylamine solution (20 ml) and THF (30 ml) was cooled to 5§C, and 3-cyanobenzoyl chloride (1.89 g) was slowly added. The mixture was stirred for one hr. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried and concentrated. The residue was recrystallized from ethyl acetate to give the title compound (1.14 g) as colorless needle crystals. 1H-NMR (CDCl3) δ: 3.06 (3H, d, J= 4.8 Hz), 6.26 (1H, brs), 7.59 (1H, t, J= 7.9 Hz), 7.80 (1H, dt, J= 7.9, 2.6 Hz), 7.95-8.10 (2H, m). IR (KBr): 3293, 2232, 1636, 1559 cm-1.

Reference： [1]Fitzmaurice, Richard J.; Gaggini, Francesca; Srinivasan, Natarajan; Kilburn, Jeremy D. [Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1706 - 1714]
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1348706, 2003, A1 Location in patent: Page/Page column 54

13
[ 1711-11-1 ]
[ 515131-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 895 mg / H₂O; tetrahydrofuran / 18 h 2: 85 percent / hydrogen / Pd/C / methanol / 72 h

Reference： [1]Fitzmaurice, Richard J.; Gaggini, Francesca; Srinivasan, Natarajan; Kilburn, Jeremy D. [Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1706 - 1714]

14
[ 1711-11-1 ]
[ 728008-84-2 ]

Yield	Reaction Conditions	Operation in experiment
72.9%		To a suspension of magnesium chloride (1.33 g) in dichloromethane (40 mL) was added 1-tert-butyl 7-ethyl 2-acetylheptanedioate (4.0 g) at ambient temperature underN2. To this mixture was added dropwise pyridine (2.26 mL) in an ice-water bath. Then the mixture was stirred at ambient temperature for 40 minutes. To the reaction mixture was added a solution of <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (3.01 g) in dichloromethane (6 mL) dropwise over 2 minutes. The reaction mixture was stirred at ambient temperature for 2 hours. To the mixture was added 1N hydrogen chloride and ethyl acetate in an ice-water bath. The organic layer was washed with 1N hydrogen chloride, water, and brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid. The residue was purified by flash silica gel chromatography (silica gel, 300 mL) eluting with hexane-ethyl acetate= 10-1, 8-1,5-1, and 3-1 to give 1-tert-butyl 7-ethyl2-acetyl-2- (3-cyanobenzoyl) heptanedioate (4.23 g, 72.9%) as colorless oil. 1-tert-Butyl 7-ethyl2-acetyl-2- (3-cyanobenzoyl)-heptanedioate NMR(CDCl3, delta) : 1.25 (3H, t, J=8Hz), 1.28-1. 40(11H, m), 1.63-1. 75 (2H, m), 2.19- 2.28 (2H, m), 2.32 (2H, t, J=8Hz), 2.45 (3H, s), 4.11 (2H, q, J=8Hz), 7.56(1H, t, J=8Hz), 7.80 (2H, dd, J=8,lHz), 7.95 (2H, dd, J=8,lHz), 8.06(1H, br s) MS(ESI+) :m/z 416 (M+H)

Reference： [1]Patent: WO2004/63197,2004,A1 .Location in patent: Page 48-49

15
[ 325125-33-5 ]
[ 1711-11-1 ]
[ 325125-34-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In dichloromethane; at 20℃; for 4h;	1.1 g (3.8 mMol) 4-[(N-tert.Butyloxycarbonyl)-pyrrolidin-3-yloxy]-benzylamin werden in 30 ml Methylenchlorid gelst und nach Zugabe von 0.9 g (9 mMol) Triethylamin portionsweise mit 1.6 g (3.8 mMol) 3-Cyanobenzoesurechlorid versetzt. Nach 4 Stunden bei Raumtemperatur wird die Lsung mit Wasser versetzt, die organische Phase wird getrocknet und eingedampft. Ausbeute: 1.5 g (94 % der Theorie), Rf-Wert: 0.27 (Kieselgel; Methylenchlorid/Essigester = 9:1)

Reference： [1]Patent: EP1206446,2004,B1 .Location in patent: Page 18

16
[ 548769-49-9 ]
[ 1711-11-1 ]
[ 812639-54-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In acetonitrile; at 20℃; for 1h;	A solution of methyl-phenyl-carbamic acid 5-amino-pyridin-2-yl ester (122 mg, 0.5mmol), <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (91 mg, 0.55 mmol) and triethylamine (56 mg, 0.55 mmol) inacetonitrile (2 ml_) was stirred at room temperature for 1 hour. Dichloromethane (3 ml_) wasadded to get a clear solution. The product was purified by flash column chromatography(SiO2), yielding the title compound (151 mg, 81% yield) as a white solid.1H NMR (300 MHz, CDCI3): S= 3.45 (br.s, 3H), 6.80 + 6.95 (2 x br.s, 1H), 7.28 (m, 1H), 7.39(m, 4H), 7.52 (t, 1H), 7.80 (d, 1H), 7.90 (br.s, 1H), 8.18 (d, 1H), 8.28 (s, 1H), 8.32 (s, 1H),9.13 (s, 1H); HPLC-MS (Method A): m/z= 373 (M+H)+; Rt = 3.52 min.

Reference： [1]Patent: WO2004/111031,2004,A1 .Location in patent: Page 59

17
[ 100-39-0 ]
[ 1711-11-1 ]
3-(2-phenylacetyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With zinc;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 0 - 20℃; for 4.5h;	10.0 g (60.4 MMOL) 3-Cyanobenzoylchlorid, 7.7 ml (64.7 MMOL) Benzylbromid und 2.0 g (2.85 MMOL) BIS-(TRIPHENYLPHOSPHIN)-PALLADIUM-(LL)-CHLORID werden IN 300 ML Tetrahydrofuran vorgelegt und unter Eiskuehlung mit 7.5 g (114.7 MMOL) Zink portionsweise versetzt. Anschliessend wird 30 Minuten unter Eiskuehlung und 4 Stunden bei Raumtemperatur geruehrt. Das Zink wird abgesaugt und die Loesung ein- gedampft. Der Rueckstand wird an Kieselgel chromatographiert, wobei mit Toluol/ Aceton 100 : 1 eluiert wird. Ausbeute : 6.8 g (41 % der Theorie) Rf-Wert : 0.91 (Kieselgel ; DICHLORMETHAN/METHANOL = 99 : 1) C15H1iN0 (221. 26) Massenspektrum : (M-H)- = 220

Reference： [1]Patent: WO2004/80970,2004,A1 .Location in patent: Page 37

18
[ 462-94-2 ]
[ 1711-11-1 ]
[ 862252-26-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃;	To a cold solution (0 C.) of 1,5-diaminopentane (0.35 mL, 3 mmol) and triethylamine (0.49 mL, 3.5 mmol) in DMF (6 mL) was added <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (550 mg, 3.3 mmol). The mixture was stirred overnight at room temperature, and then diluted with water (40 mL). The beige solid that precipitated was collected by filtration and dried in vacuo, giving the corresponding amide, 500 mg, 1.39 mmol, 90% yield.
90%	With triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃;	To a cold solution (0 C) of 1,5-diaminopentane (0.35 mL, 3 mmol) and triethylamine (0.49 mL, 3.5 mmol) in DMF (6 mL) was added <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (550 mg, 3.3 mmol). The mixture was stirred overnight at room temperature, and then diluted with water (40 mL). The beige solid that precipitated was collected by filtration and dried in vacuo, giving the corresponding amide, 500 mg, 1.39 mmol, 90 % yield.

Reference： [1]Patent: US2005/182118,2005,A1 .Location in patent: Page/Page column 35
[2]Patent: WO2005/79780,2005,A1 .Location in patent: Page/Page column 71

19
[ 305447-46-5 ]
[ 1711-11-1 ]
[ 305447-55-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine; In tetrahydrofuran; at 20℃; for 2h;	Preparation of (3-Cyanophenyl)-N-[4-(1-hydroxy-1-methyl-2-[(methylethyl)sulfonyl]amino}ethyl)phenyl]carboxamide Scheme XII, Step A: Into a 100 mL single-neck flask, 91 mg of <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> was added dropwise to 135 mg of [2-(4-aminophenyl)-2-hydroxypropyl][(methylethyl)sulfonyl]amine (prepared in example 19) and 56 mg of triethylamine in THF (20 mL) while stirring under a nitrogen atmosphere at room temperature. The reaction was allowed to stir at this temperature for 2 h. The mixture was then poured into H2O and the desired product was extracted into ethyl acetate. The organic layer was backwashed once with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 254 mg as a solid. This material was purified via silica gel chromatography employing the Chromatotron, using a 2000 micron rotor and eluding with a solvent of ethyl acetate to yield the intermediate title compound (131 mg, 66%) as an oil. Ion spray M.S. 400.1 (M*-1). Calculated for: C20H23N3O4S:

Reference： [1]Patent: US7034045,2006,B1 .Location in patent: Page/Page column 55-56

20
[ 1711-11-1 ]
[ 3441-01-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In dichloromethane;	Preparation 79 3-Cyanobenzamide 0.88 Ammonia solution (30 ml) was slowly added to a solution of 3-cyanobenzoyl chloride (10 g, 60.3 mmol) in dichloromethane (100 ml) at 0° C. under nitrogen and the reaction was stirred for 20 minutes. The mixture was filtered and the solid was washed with water (50 ml) then diethylether (50 ml), azeotroped with toluene and dried in vacuo to provide the title compound (9 g) as a white solid. 1H NMR (400 MHz, CD3OD): delta=7.62 (m, 1H), 7.86 (m, 1H), 8.12 (m, 1H), 8.18 (s, 1H).
	With ammonia; water; In tetrahydrofuran; at 5℃; for 1h;	i) Production of 3-cyanobenzamide A mixture of 28percent aqueous ammonia (20 ml) and THF (30 ml) was cooled to 5C and 3-cyanobenzoyl chloride (1.45 g) was slowly added. The mixture was stirred for one hr. and the reaction mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was recrystallized from ethyl acetate to give the title compound (802 mg) as colorless needle crystals. 1H-NMR (CDCl3+CD3OD)delta: 7.61 (1H, t, J= 7.8 Hz), 7.82 (1H, dt, J= 7.8, 1.4 Hz), 8.13 (1H, dt, J= 7.8, 1.4 Hz), 8.21 (1H, t, J= 1.4 Hz). IR (KBr): 3420, 3160, 2232, 1705, 1397 cm-1.

Reference： [1]Patent: US2003/100554,2003,A1
[2]Patent: EP1348706,2003,A1 .Location in patent: Page/Page column 53

21
aq. NH₄Cl [ No CAS ]
[ 1711-11-1 ]
[ 215656-99-8 ]
[ 219518-89-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine; In dichloromethane;	B N-(3-cyanobenzoyl)-2-nitro-4-(dimethyl-t-butylsiloxy)aniline To a mixture of 2-nitro-4-(dimethyl-t-butylsiloxy)aniline (10.01 g, 37.30 mmol) and CH2Cl2 (400 mL) at 0 C was added pyridine (3.4 mL, 42.0 mmol) followed by the <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (8.65 g, 52.2 mmol). The reaction was allowed to warm to room temperature and stirred for 1 h. The reaction was diluted with CH2Cl2 (800 mL) and washed with sat. aq. NH4Cl (2*200 mL). The organic layer was MgSO4 dried, filtered, and concentrated. The residue was chromatographed (20% EtOAc/hexanes) to give the title compound as a solid (13.94 g, 94%); IR(CHCl3): 2932, 1689, 1508, 1289, 863 cm-1; NMR(300 MHz, CDCl3): delta0.27 (s, 6H), 1.02 (s, 9H), 7.27 (s, 1H), 7.70 (m, 2H), 7.90 (d, J=7.8, 1H), 8.16 (d, J=1.2, 1H), 8.30 (s, 1H), 8.79 (d, J=9.3, 1H), 11.15 (br s, 1H); MS(FD): 397.0. Analysis for C20H23N3O4Si: Calculated: C, 60.43; H, 5.83; N, 10.57. Found: C, 60.58; H, 5.79; N, 10.61.

Reference： [1]Patent: US6417200,2002,B1

22
[ 473547-54-5 ]
[ 62088-13-5 ]
[ 1711-11-1 ]
[ 473548-82-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example M1 {4-Chloro-2-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-5-dimethylamino-phenyl}-carbamic acid tert.-butyl ester The title compound was prepared from (2-amino-4-chloro-5-dimethylamino-phenyl)-carbamic acid tert.-butyl ester (Example J1) (0.5 mmol) and <strong>[62088-13-5]3-(3-cyano-phenyl)-3-oxo-propionic acid ethyl ester</strong> [CAS-No. 62088-13-5; prepared from 3-cyanobenzoyl chloride according to general procedure K, method a] (0.55 mmol) according to the general procedure M. Obtained as a white solid (160 mg). MS (ISP) 457 [(M+H)+]; mp 159-163 C.

Reference： [1]Patent: US6544985,2003,B2

23
[ 1711-11-1 ]
[ 127942-30-7 ]
[ 206882-10-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In tetrahydrofuran; water	R.1.2 Step 2 Step 2 In 15 ml of dried tetrahydrofuran, 968 mg of 2-amino-4-ethoxycarbonyl-1,3-thiazolehydrobromide were suspended. To the suspension, 1.19 g of triethylamine were added. A solution of 3-cyanobenzoyl chloride dissolved in 3 ml of dried tetrahydrofuran was added dropwise to the resulting mixture under ice cooling, followed by stirring at room temperature for 3 hours. Water was added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (chloroform: methanol=10:1), whereby 980 mg of 2-[N-(3-cyanobenzoyl)amino]-4-ethoxycarbonyl-1,3-thiazole were obtained as white crystals. Yield: 83%. Melting point: 203.0 to 204.5° C.

Reference： [1]Current Patent Assignee: ZERIA PHARMACEUTICAL CO LTD - US6121301, 2000, A

24
[ 1711-11-1 ]
[ 75-65-0 ]
[ 383185-76-0 ]

Yield	Reaction Conditions	Operation in experiment
82.1%	With pyridine;dmap; In dichloromethane; at 0 - 20℃; for 20h;	To a mixture of tert-butanol (3.50 g, 47.22 mmol), pyridine (3.72 g, 46.78 mmol) and cat. DMAP in methylene chloride (15 mL) is added dropwise <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (6.81 g, 41.07 mmol) and pyridine (3 mL) in methylene chloride (10 mL) at 0 C. The resulting mixture is stirred at room temperature for 20 h. The solvent is evaporated, and the residue is purified by flash chromatography (1:1 methylene EPO <DP n="84"/>chloride/hexanes) to afford 3-cyano-benzoic acid tert-butyl ester (6.84 g, 82.1% yield) as white solid. 1H NMR (300 MHz, CDCl3): delta 8.24 (1H, s), 8.20 (1H, dd, J = 7.9, 1.2 Hz), 7.78 (1H, dd, J= 6.7, 1.1 Hz), 7.52 (1H, m), 1.58 (9H, s).

Reference： [1]Patent: WO2006/44505,2006,A2 .Location in patent: Page/Page column 82-83

25
[ 444289-05-8 ]
[ 1711-11-1 ]
3-cyano-N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In tetrahydrofuran; at 5 - 20℃; for 5h;	5.12 3-CYANO-N-[2-(2,6-DIOXO-PIPERIDIN-3-YL)-1-OXO-2,3-DIHYDRO-1H-ISOINDOL-4-YLMETHYL]-BENZAMIDE A suspension of 3-(4-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrochloride (0.7 g, 2.1 mmol) and <strong>[1711-11-1]m-cyanobenzoyl chloride</strong> (0.4 g, 2.5 mmol) in THF (30 mL) was cooled to 5 C. Triethylamine (0.5 g, 4.8 mmol) was added, and the mixture was stirred at room temperature for 5 hours. The mixture was concentrated, and the residue was stirred with 1N HCl (40 mL). The mixture was filtered, and the solid was slurried with warmed ethanol (20 mL) to give 3-cyano-N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-benzamide (0.8 g, 92%) as a white solid: mp 282-284 C.; 1H NMR (DMSO-d6) delta 2.01-2.06 (m, 1H), 2.34-2.65 (m, 2H), 2.86-3.00 (m, 1H), 4.41-4.62 (m, 4H, 2CH2), 5.11-5.18 (dd, J=4.8 and 13 Hz, 1H, CH), 7.48-7.74 (m, 4H, Ar), 8.01 (d, J=7.7 Ha, 1H, Ar), 8.17 (d, J=7.9 Hz, 1H, Ar), 8.31 (s, 1H, Ar), 9.28 (t, J=5.0 Hz, 1H, NH), 11.01 (s, 1H, NH); 13C NMR (DMSO-d6) delta 22.69, 31.17, 46.26, 51.60, 111.50, 118.26, 121.79, 128.35, 129.80, 130.82, 130.89, 131.65, 132.08, 134.14, 134.79, 135.00, 140.25, 164.54, 168.02, 170.98, 172.81; Anal. calcd. for C22H18N4O4: C, 65.67; H, 4.51; N, 13.92. Found: C, 65.38; H, 4.42; N, 13.77.

Reference： [1]Patent: US2007/49618,2007,A1 .Location in patent: Page/Page column 56

26
[ 1536-18-1 ]
[ 1711-11-1 ]
3-{4-[(4-trifluoromethylphenyl)phenylmethyl]piperazine-1-carbonyl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; triethylamine; In 1,2-dichloro-ethane; at 20℃;	To a 0.075 M 1,2-dicholoroethane solution of l-[phenyl-(4-trifluoromethyl-phenyl)- methyl]-piperazine-2 HCl (200 muL, 15 mumol), triethylamine (4.8 mg, 48 mumol), and DMAP (0.17 mg, 1.5 mumol) was added 144 muL of a 0.15 M solution of <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (21.6 mumol) in 1,2-dichloroethane. The mixture was stirred overnight at room temperature, then filtered on hydromatrix-filled filter pre-treated with 500 muL of 2N NaOH solution. The hydromatrix was washed with 500 muL of dichloromethane and evaporated to dryness in the Genevac. Estimated yield from combichem plates: 6.1 mg (90%). 1H NMR (500 MHz, DMSO-dbeta) delta 2.25-2.50 (m, 4H), 3.30-3.50 (m, 4H), 4.52 (s, IH), 7.22 (dd, J= 7.5, 7.5 Hz, IH), 7.32 (dd, J= 7.5, 7.5 Hz, 2H), 7.44 (d, J= 7.5 Hz, 2H), 7.63 (dd, J= 7.5, 7.5 Hz, IH), 7.65-7.68 (m, 4H), 7.69 (d, J= 7.5 Hz, IH), 7.85 (s, IH), 7.90 (d, J= 7.5 Hz, IH); +ES MS (M+l) 449.2.

Reference： [1]Patent: WO2007/18459,2007,A1 .Location in patent: Page/Page column 35

27
[ 7446-70-0 ]
[ 16766-27-1 ]
[ 1711-11-1 ]
[ 119-61-9 ]

Yield	Reaction Conditions	Operation in experiment
		4 Benzophenone-like Phosphonate NNRTI Compounds For example (Example 1), commercially available 3-cyanobenzoyl chloride is treated with trichloroaluminum followed by 3,4-dimethoxy chlorobenzene to give benzophenone 8a.
		N.4 Efavirenz Example 4 For example (Benzophenone Example 1), commercially available 3-cyanobenzoyl chloride is treated with trichloroaluminum followed by 3,4-dimethoxy chlorobenzene to give benzophenone 8a.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - US2004/121316, 2004, A1
[2]Current Patent Assignee: GILEAD SCIENCES INC - US2005/239054, 2005, A1

28
[ 1594-58-7 ]
[ 1711-11-1 ]
[ 913830-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; for 4h;Heating / reflux;	3-(3-(pyridin-3-yl)-1 ,2,4-oxadiazol-5-yl)benzonithle 3-Pyridylamideoxime (Aldrich, 5.5 g, 40 mmol) was dissolved in 60 mL of pyridine and 3-cyanobenzoyl chloride (Aldrich, 6.6 g, 40 mmol) was added. The reaction mixture was heated to reflux for 4 hours and then cooled to room temperature. The solution was poured into water (500 mL), filtered, and the solid were collected and dried under vacuum. ^ H NMR (300 MHz, methanol- d4) delta ppm 7.87 (td, J=8.0, 0.7 Hz, 1 H), 8.10 (dt, J=8.1 , 1.4 Hz, 1 H), 8.23 (ddd, J=8.1 , 5.6, 0.8 Hz, 1 H), 8.56 (ddd, J=8.0, 1.7, 1.2 Hz, 1 H), 8.64 (td, J=1 .7, 0.7 Hz, 1 H), 9.04 (dd, J=5.4, 1 .0 Hz, 1 H), 9.23 (dt, J=8.1 , 1 .7 Hz, 1 H), 9.57 (d, J=1.7 Hz, 1 H); MS (+ESI) m/z 249 (M+H)+.
	With pyridine; for 4h;Reflux;	3-Pyridylamideoxime (Aldrich, 5.5 g, 40 mmol) was dissolved in 60 mL of pyridine and 3-cyanobenzoyl chloride (Aldrich, 6.6 g, 40 mmol) was added. The reaction mixture was heated to reflux for 4 hours and then cooled to room temperature. The solution was poured into water (500 mL), filtered, and the solid were collected and dried under vacuum. 1H NMR (300 MHz, CD3OD) delta ppm 7.87 (td, J=8.0, 0.7 Hz, 1 H), 8.10 (dt, J=8.1, 1.4 Hz, 1 H), 8.23 (ddd, J=8.1, 5.6, 0.8 Hz, 1 H), 8.56 (ddd, J=8.0, 1.7, 1.2 Hz, 1 H), 8.64 (td, <n="46"/>J=1.7, 0.7 Hz, 1 H), 9.04 (dd, J=5.4, 1.0 Hz, 1 H), 9.23 (dt, J=8.1, 1.7 Hz, 1 H), 9.57 (d, J=I.7 Hz, 1 H); MS (+ESI) m/z 249 (M+H)+.

Reference： [1]Patent: WO2008/73942,2008,A2 .Location in patent: Page/Page column 35
[2]Patent: WO2009/148452,2009,A1 .Location in patent: Page/Page column 44-45

29
[ 79023-51-1 ]
[ 1711-11-1 ]
[ 394648-09-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of diisopropylamine (0.43 ml) in tetrahydrofuran (5 ml) was added n-butyl lithium (1.6M in hexane, 2.15 ml) and the mixture was stirred for 30 minute at 0 C. To the reaction mixture was added a solution of the compound prepared in reference example 2 (478 mg) in tetrahydrofuran (2 ml) dropwise at -78 C. and the mixture was stirred for 90 minutes at -78 C. To the reaction mixture was added 3-cyanobenzoyl chloride (571 mg) in tetrahydrofuran (2 ml) dropwise and then it was stirred under warming to -10 C. over a period of 90 minutes. To the reaction mixture was added water and was extracted with ether twice. The extract was washed with 1N hydrochloric acid, water and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1?10:1) to give the compound of the present invention (61 mg) having the following physical data. TLC: Rf0.49 (hexane:ethyl acetate=2:1); NMR (CDCl3): delta 11.89 (br, 1H), 8.22 (dd, J=1.5, 1.5 Hz, 1H), 8.17 (ddd, J=7.5, 1.5, 1.5 Hz, 1H), 7.83 (d, J=7.0 Hz, 1H), 7.71 (ddd, J=7.5, 1.5, 1.5 Hz, 1H), 7.55 (dd, J=7.5, 7.5 Hz, 1H), 7.47 (t, J=7.0 Hz, 1H), 7.38 (t, J=7.0 Hz, 1H), 7.24 (d, J=7.0 Hz, 1H), 6.25 (s, 1H), 2.93 (s, 2H), 1.38 (s, 6H).

Reference： [1]Patent: US2005/222138,2005,A1 .Location in patent: Page/Page column 129

30
[ 768-57-0 ]
[ 1711-11-1 ]
[ 1223726-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h;	6.1.39 6.1.39. Synthesis of Compound LII; [001225] To a stirred solution 4-(furan-2-yl)butan-2-amine (0.5 mmol) in dichloromethane (2 rnL) at room temperature, was added diisopropylethylamine (0.75 mmol) and 3-cyanobenzoyl chloride (0.5 mmol). The reaction was stirred for 5 h at room temperature and then quenched with MeOH. The reaction mixture was extracted into DCM and the organic layer was washed with water and brine. The solvent was evaporated in vacuo, and the residue was purified by reverse-phase HPLC and analyzed for purity by LCMS and 1H NMR. RP-HPLC (H2O/ACN(10- 95%) 1 ml/min, 4.5 min, 254 nM): Ret. Time = 3.06 min; ESI-MS m/z 269 [M+H]+.

Reference： [1]Current Patent Assignee: CELLADON CORP - WO2010/88450, 2010, A2 Location in patent: Page/Page column 264

31
[ 1021926-19-1 ]
[ 1711-11-1 ]
[ 1357168-36-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In 1,4-dioxane; at 20℃;Inert atmosphere;	General procedure: K2CO3 (5 mmol, 5eq) and substituted acyl chloride (1.2 mmol, 1.2 eq) were successively added to a solution of the aniline e (1.0 mmol, 1.0 eq) in 3 mL dry 1, 4 -dioxane and the mixture was stirred at room temperature overnight. 10 mL H2O and 3 mL saturated aqueous Na2CO3 was added to the mixture and it was stirred at room temperature overnight. The precipitated solid was collected by filtration and purified by silica gel column chromatography.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 432 - 444

32
[ 1772-01-6 ]
[ 1711-11-1 ]
3-(2′-pyridyl)-5-(3′-cyanophenyl)-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine; In toluene;Reflux;	General procedure: The synthesis of 1,2,4-oxadiazoles has been performed by theamidoxime route [35]. The appropriate amidoxime (0.3 g) wasdissolved in 50 mL of toluene in a 250 mL round bottomed flask.Then,1.2 eq. of the appropriate aroyl chloride and 1.2 eq. of pyridinewere added and the reaction mixture was refluxed for 6e8 hmonitoring the reaction by TLC until consumption of starting material. The solvent was removed under vacuum and water wasadded to the residue. Extraction with ethyl acetate and chromatographic separation on silica gel using mixtures of petroleum etherand ethyl acetate as eluent allowed to obtain the desired oxadiazole, further purified by crystallization.3-(2?-pyridyl)-5-(3?-cyanophenyl)-1,2,4-oxadiazole (NV1859).(0.49 g; 89% Yield). White solid, m.p. 148e149 C from petroleumether (lit. [36].148e149 C). 1H NMR (300 MHz, CDCl3): d (ppm)8.86 (dd, 1H, J1 10.0 Hz, J2 4.8 Hz), 8.60 (brs, 1H), 8.52 (1H, d,J 8.0 Hz), 8.23 (1H, d, J 8.0 Hz), 7.90 (2H, m), 7.73 (1H, t,J 7.8 Hz), 7.49 (1H, dd, J1 8.0 Hz, J2 4.8 Hz); 13C NMR (75 MHz,CDCl3): d (ppm) 174.38,169.01,150.55,145.93,137.19,135.88,132.07,131.75, 130.22, 125.82, 125.30, 123.36, 117.34, 113.88; HRMS forC14H8N4O found 249.0782 [MH] (Calcd. 249.0771).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 429 - 435
[2]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 6974 - 6979,6

33
[ 55459-60-4 ]
[ 1711-11-1 ]
[ 1427265-39-1 ]

Yield	Reaction Conditions	Operation in experiment
		According to Scheme 1 , steps 2-3: To a solution of 1 -(4-morpholin-4-yl-3,6-dihydro- 2H-pyridin-1 -yl)-ethanone (1 ) (6.35 g, 30.2 mmol) in dry dichloromethane (30 ml) at 0C was added triethylamine (3.056 g, 30.2 mmol) and after stirring the solution at 0C for 10 min, <strong>[1711-11-1]3-cyanobenzochloride</strong> (5 g, 30.2 mmol) was added. The mixture was stirred for 45 min at 0C then the mixture was allowed to warm to room temperature and stirred overnight. 5% aqueous HCI was added and the mixture was stirred for 2 h. The mixture was extracted with dichloromethane and the organic layer was washed with water, filtered over a short pad of silica gel and evaporated to dryness resulting in 8 g of 3-(1 -Acetyl-4-oxo-piperidine-3-carbonyl)-benzonitrile (2a) which was used immediately in the next step without purification.
		3-(5-Acetyl-4,5,6,7-tetrahydro-1 H-pyrazolo[4,3-c]pyridin-3-yl)-benzonitrile (3a)According to Scheme 1 , method A: steps 2-3: to a solution of 1 -(4-Morpholin-4-yl- 3,6-dihydro-2H-pyridin-1 -yl)-ethanone (1 ) (6.35 g, 30.2 mmol) in drydichloromethane (30 ml) at 0C was added triethylamine (3.056 g, 30.2 mmol) and after stirring the solution at 0C for 10 min, <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (5 g, 30.2 mmol) was added. The mixture was stirred for 45 min at 0C then the mixture was allowed to warm to room temeperature and stirred overnight. 5% aqueous HCI was added and the mixture was stirred for 2 h. The mixture was extracted with dichloromethane and the organic layer was washed with water, filtered over a short pad of silica gel and evaporated to dryness to give 8 g of 3-(1 -Acetyl-4-oxo- piperidine-3-carbonyl)-benzonitrile (2a) which was used immediately in the next step without purification.
8 g		According to Scheme 1 , method A: steps 2-3: to a solution of 1 -(4-Morpholin-4-yl- 3,6-dihydro-2H-pyridin-1 -yl)-ethanone (1 ) (6.35 g, 30.2 mmol) in drydichloromethane (30 ml) at 0C was added triethylamine (3.056 g, 30.2 mmol) and after stirring the solution at 0C for 10 min, <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (5 g, 30.2 mmol) was added. The mixture was stirred for 45 min at 0C then the mixture was allowed to warm to room temeperature and stirred overnight. 5% aqueous HCI was added and the mixture was stirred for 2 h. The mixture was extracted with dichloromethane and the organic layer was washed with water, filtered over a short pad of silica gel and evaporated to dryness to give 8 g of 3-(1 -Acetyl -4-oxo- piperidine-3-carbonyl)-benzonitrile (2a) which was used immediately in the next step without purification.

8 g		According to Scheme 1 , steps 2-3: To a solution of 1 -(4-morpholin-4-yl-3,6-dihydro- 2H-pyridin-1 -yl)-ethanone (1 ) (6.35 g, 30.2 mmol) in dry dichloromethane (30 ml) at 0C was added triethylamine (3.056 g, 30.2 mmol) and after stirring the solution at 0C for 10 min, <strong>[1711-11-1]3-cyanobenzochloride</strong> (5 g, 30.2 mmol) was added. The mixture was stirred for 45 min at 0C then the mixture was allowed to warm to room temperature and stirred overnight. 5% aqueous HCI was added and the mixture was stirred for 2 h. The mixture was extracted with dichloromethane and the organic layer was washed with water, filtered over a short pad of silica gel and evaporated to dryness resulting in 8 g of 3-(1 -Acetyl-4-oxo-piperidine-3-carbonyl)-benzonitrile (2a) which was used immediately in the next step without purification.
8 g		According to Scheme 1, method A: steps 2-3: to a solution of 1-(4-Morpholin-4-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (1) (6.35 g, 30.2 mmol) in dry dichloromethane (30 ml) at 0 C. was added triethylamine (3.056 g, 30.2 mmol) and after stirring the solution at 0 C. for 10 min, <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (5 g, 30.2 mmol) was added. The mixture was stirred for 45 min at 0 C. then the mixture was allowed to warm to room temperature and stirred overnight. 5% aqueous HCl was added and the mixture was stirred for 2 h. The mixture was extracted with dichloromethane and the organic layer was washed with water, filtered over a short pad of silica gel and evaporated to dryness to give 8 g of 3-(1-Acetyl-4-oxo-piperidine-3-carbonyl)-benzonitrile (2a) which was used immediately in the next step without purification. To a mixture of 3-(1-Acetyl-4-oxo-piperidine-3-carbonyl)-benzonitrile (2a) (8 g, 29.6 mmol) in ethanol (26 ml) at 10 C. hydrazine hydrate (4.44 g, 88.8 mmol) was added slowly within 5 min. The mixture was stirred 3 h and allowed to warm to room temperature overnight. The mixture was concentrated to 1/4 of its volume until a precipitate formed. The suspension was stirred for 2 h, cooled down and filtrated. The solid was washed with a small amount of ethanol. A second portion of product precipitated overnight from the filtrate and was pooled with the first portion of solid to give 4.02 g of 3-(5-Acetyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-benzonitrile (3a) as a solid. Rt=1.20 min (LC-method 7). Detected mass: 267.15 [M+H+]
8 g		According to Scheme 1, steps 2-3: To a solution of 1-(4-morpholin-4-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (1) (6.35 g, 30.2 mmol) in dry dichloromethane (30 ml) at 0 C. was added triethylamine (3.056 g, 30.2 mmol) and after stirring the solution at 0 C. for 10 min, <strong>[1711-11-1]3-cyanobenzochloride</strong> (5 g, 30.2 mmol) was added. The mixture was stirred for 45 min at 0 C. then the mixture was allowed to warm to room temperature and stirred overnight. 5% aqueous HCl was added and the mixture was stirred for 2 h. The mixture was extracted with dichloromethane and the organic layer was washed with water, filtered over a short pad of silica gel and evaporated to dryness resulting in 8 g of 3-(1-Acetyl-4-oxo-piperidine-3-carbonyl)-benzonitrile (2a) which was used immediately in the next step without purification.

Reference： [1]Patent: WO2013/37736,2013,A1 .Location in patent: Page/Page column 35
[2]Patent: WO2013/37415,2013,A1 .Location in patent: Page/Page column 52-53
[3]Patent: WO2013/37914,2013,A1 .Location in patent: Page/Page column 55-56
[4]Patent: WO2013/37389,2013,A1 .Location in patent: Page/Page column 33-34
[5]Patent: US2014/330009,2014,A1 .Location in patent: Paragraph 0412-0415
[6]Patent: US2014/378686,2014,A1 .Location in patent: Paragraph 0130

34
[ 109-01-3 ]
[ 1711-11-1 ]
[ 1016743-09-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In dichloromethane; at 20℃; for 6h;	Step 1: 3-[(4-Methylpiperazin-1-yl)carbonyl]benzenecarbonitrile A solution of <strong>[1711-11-1]3-cyanobenzoic acid chloride</strong> in 100 ml of methylene chloride was added dropwise to a solution of 4.57 g (45.6 mmol) of 1-methylpiperazine and 8.5 ml (60.8 mmol) of triethylamine in 100 ml of methylene chloride at 0 C. The mixture was then stirred at RT for 6 h. 200 ml of water were then added, the phases were separated and the organic phase was washed with water. After drying over anhydrous magnesium sulfate, the mixture was filtered and the solvent was removed on a rotary evaporator. 6.9 g (99% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 7.72 (d, 1H), 7.70 (s, 1H), 7.65 (d, 1H), 7.55 (t, 1H), 3.80 (broad, 2H), 3.40 (broad, 2H), 2.50 (broad, 2H), 2.37 (broad, 2H), 2.34 (s, 3H). LC/MS (method I, ESIpos): Rt=0.21 min, m/z=230 [M+H]+. GC/MS (method L, ESIpos): Rt=7.36 min, m/z=229 [M]+.

Reference： [1]Patent: US2013/196964,2013,A1 .Location in patent: Paragraph 1132; 1133; 1134; 1135; 1136

35
[ 1711-11-1 ]
[ 203268-77-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 0 °C 2: hydrazine hydrate / methanol / 5 h / Reflux 3: potassium hydroxide / methanol / 20 °C / Reflux 4: hydrogenchloride / water / 0 - 5 °C

Reference： [1]Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194]

36
[ 109-97-7 ]
[ 1711-11-1 ]
[ 1528751-38-3 ]

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: To a freshly prepared solution of ethylmagnesium bromide (90 mmol) in diethyl ether (32 mL) was added dropwise a solution of pyrrole (6.06 mL, 5.86 g, 87.3 mmol) in diethyl ether (40 mL) under reflux. After the addition was complete, the solution was refluxed for a further 30 min. Then the reaction mixture was cooled to room temperature, and the appropriate aroyl chloride (104.9 mmol) dissolved in diethyl ether or tetrahydrofuran (100 mL) was added dropwise over a period of 1 h. The solution was stirred overnight. The reaction mixture was then poured onto a concentrated aqueous ammonium chloride solution (200 mL), extracted with dichloromethane (200 mL), the organic layer was washed with water (3×100 mL), dried over MgSO4, filtered, and evaporated. The crude material was purified by flash chromatography (Merck 107736 Silica gel 60 H, toluene), and recrystallized from the appropriate solvent (given after melting point data in parentheses).

Reference： [1]Tetrahedron,2014,vol. 70,p. 465 - 476

37
[ 1607465-43-9 ]
[ 1711-11-1 ]
[ 1607465-30-4 ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: A stirred solution of 12 (0.19mmol) in CH2Cl2 was cooled to 0C in an ice bath, and triethylamine (0.29mmol) was added. The mixture was stirred for 20min, and to it, benzoyl chloride (13a) (0.23mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 1h. The reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using MeOH/CH2Cl2 (1:20) as eluent to afford the titled compound as a light yellow solid. Yield 82%.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2724 - 2732

38
[ 106-47-8 ]
[ 1711-11-1 ]
[ 865660-61-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In dichloromethane at 0 - 20℃; for 2h;

Reference： [1]Zhu, Weixing; Haupenthal, Jörgm; Groh, Matthias; Fountain, Michelle; Hartmann, Rolf W. [Antimicrobial Agents and Chemotherapy, 2014, vol. 58, # 7, p. 4242 - 4245]

39
[ 578-66-5 ]
[ 1711-11-1 ]
3-cyano-N-(quinolin-8-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.5h;	[00430] 3-Cyanobenzoyl chloride (1.0 mmol) was dissolved in dichioromethane (2 mL) and cooled to 0 C. This solution was added dropwise to a cooled (0 C) solution of 8- aminoquinoline (144 mg, 1.0 mmol) and N,N-diisopropylethylamine (260 jiL, 1.5 mmol) in dichloromethane (5 mL). After addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hrs. The mixture was diluted with water and extracted with 2 volumes of dichloromethane. The organic layers were collected and the solvent was removed by rotary evaporation. The residue was purified by preparative reverse-phase HPLC using a water-acetonitrile gradient to afford compound B3. ESI-MS: m/z 274 [M+H]+.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.5h;	3-Cyanobenzoyl chloride (1.0 mmol) was dissolved in dichloromethane (2 mL) and cooled to 0 C. This solution was added dropwise to a cooled (0 C.) solution of 8-aminoquinoline (144 mg, 1.0 mmol) and N,N-diisopropylethylamine (260 muL, 1.5 mmol) in dichloromethane (5 mL). After addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hrs. The mixture was diluted with water and extracted with 2 volumes of dichloromethane. The organic layers were collected and the solvent was removed by rotary evaporation. The residue was purified by preparative reverse-phase HPLC using a water-acetonitrile gradient to afford compound B3. ESI-MS: m/z 274 [M+H]+.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 14349 - 14352
[2]Chemistry - A European Journal,2016,vol. 22,p. 1362 - 1367
[3]Organic Letters,2016,vol. 18,p. 1698 - 1701
[4]Patent: WO2016/32569,2016,A1 .Location in patent: Page/Page column 198
[5]Patent: US2019/151303,2019,A1 .Location in patent: Paragraph 0671

40
[ 1711-11-1 ]
[ 229343-30-0 ]
N-{4-chloro-2-[N-(5-chloro(pyridin-2-yl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With pyridine; In dichloromethane; at 20℃;	Step 2: To a solution of the compound of (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (0.71 g, 2.52 mmol) in dichloromethane (10 ml) was added 3-cyanobenzoly chloride (417 mg, 2.52 mmol) and pyridine (0.611 ml, 7.55 mmol). The mixture was stirred at r.t. overnight. The precipitate was filtered and washed with dichloromethane to give N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide as a solid (683 mg, 66%). MS found for C20H12Cl2N4O2 M+=411, (M+2)+=413.

Reference： [1]Patent: US9108922,2015,B2 .Location in patent: Page/Page column 273-274

41
[ 1711-11-1 ]
[ 280773-05-9 ]
N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methylphenyl}(4-cyanophenyl)carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With pyridine; In dichloromethane; at 20℃;	Step 3: To a solution of the compound of (2-aminophenyl)-N-(2-pyridyl)carboxamide, C, chloride, N (1.36 g, 5.2 mmol) in dichloromethane (10 ml) was added 3-cyanobenzoly chloride (860 mg, 5.2 mmol) and pyridine (1.26 ml, 15.6 mmol). The mixture was stirred at r.t. overnight. After the evaporation of the solvent, the crude residue was purified by silica gel column chromatography using solvent system 25% ethyl acetate in hexane as eluent to give N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methylphenyl}(4-cyanophenyl)carboxamide as a solid (830 mg, 41%). MS found for C21H15ClN4O2 M+=390, (M+2)+=392.

Reference： [1]Patent: US9108922,2015,B2 .Location in patent: Page/Page column 283

42
(2-amino-3,4,5-trimethoxyphenyl)-N-(5-bromo(2-pyridyl))carboxamide [ No CAS ]
[ 1711-11-1 ]
N-{6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}(4-cyanophenyl)carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine; In dichloromethane; at 20℃;	Step 3: To a solution of the compound of (2-amino-3,4,5-trimethoxyphenyl)-N-(5-bromo(2-pyridyl))carboxamide (570 mg, 1.49 mmol) in dichloromethane (5 ml) was added 3-cyanobenzoly chloride (247 mg, 1.49 mmol) and pyridine (0.362 ml, 4.48 mmol). The mixture was stirred at r.t. overnight. After the evaporation of the solvent, the crude residue was purified by silica gel column chromatography using solvent system 25% ethyl acetate in hexane as eluent to give N-{6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}(4-cyanophenyl)carboxamide as a solid (680 mg, 69%). MS found for C23H19BrN4O5 M+=511, (M+2)+=513.

Reference： [1]Patent: US9108922,2015,B2 .Location in patent: Page/Page column 286

43
tert-butyl 4-(5-amino-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate [ No CAS ]
[ 1711-11-1 ]
tert-butyl 4-(5-(3-cyanobenzamido)-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In dichloromethane; at 20℃; for 1.5h;	To an ice-cold solution of tert-butyl 4-(5-amino-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate (100 mg, 0.30 mmol) and <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (55 mg, 0.33 mmol) in DCM (5 ml) was added triethylamine (169 mul, 1.21 mmol). The temperature was allowed to room temperature and the mixture was stirred for 90 min. The solvents were evaporated and the residue was purified by flash chromatography to provide 105 mg (76%) of the title compound. LC/MS (20-100% CH3CN:0.05% HCOOH(aq) gradient over 5 min): 2.85 min. 460 M+H.

Reference： [1]Patent: US2016/46597,2016,A1 .Location in patent: Paragraph 0208

44
(4-(5-amino-1,4-dimethyl-1H-indol-3-yl)piperidin-1-yl)-(cyclopentyl)methanone [ No CAS ]
[ 1711-11-1 ]
3-cyano-N-(3-(1-(cyclopentanecarbonyl)piperidin-4-yl)-1,4-dimethyl-1H-indol-5-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine; In dichloromethane; at 20℃; for 20h;Cooling with ice;	(4-(5-amino-1,4-dimethyl-1H-indol-3-yl)piperidin-1-yl)(cyclopentyl)methanone (0.84 g, 2.5 mmol) was dissolved in DCM (50 mL), and the mixture was cooled in an ice-water bath. Triethylamine (1.14 mL, 8.16 mmol) was added over 2 min, followed by <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (0.68 g, 4.1 mmol) in one portion. The mixture was allowed to reach room temperature, and was then stirred for 20 h. Water was added and the mixture was then extracted four times with EtOAc. The combined organics were washed with brine, dried (Na2SO4), and evaporated. The crude product was purified by prep-HPLC to provide 0.73 g (62%) as an off-white foamy solid. 1H NMR (500 MHz, (CD3)CO) delta ppm 8.38 (d, 1H, J=8.3 Hz), 7.99 (d, 1H, J=8.0 Hz), 7.78 (t, 1H, J=7.7 Hz), 7.20 (d, 1H, J=8.5 Hz), 7.16 (d, 1H, J=8.5 Hz), 7.09 (s, 1H), 4.72 (d, 1H, J=12.9 Hz), 4.19 (d, 1H, J=13.2 Hz), 3.77 (s, 3H), 3.41 (m, 1H), 3.23 (m, 1H), 3.05 (m, 1H), 2.68 (m, 1H), 2.63 (s, 3H), 2.14 (m, 1H), 2.02 (m, 1H) and 1.83-1.45 (m, 10H). LCMS: m/e 469 [M+H].

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 10415 - 10439
[2]Patent: US2016/46597,2016,A1 .Location in patent: Paragraph 0291

45
2-(4-phenylthiazol-2-yl)ethylamine hydrobromide [ No CAS ]
[ 1711-11-1 ]
2-[2-(3-cyanobenzamido)]ethyl-4-phenylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In tetrahydrofuran; at 0 - 20℃;	General procedure: A suspension of 4-phenylthiazol-2-ethylamine hydrobromide(89a, 1-1.1 mmol, 1 equiv) and the appropriate acyl halide (minimum of 1.2 equiv) in THF (10 mL) was chilled to 0 C. Triethylamine(minimum of 3 equiv) was added and the mixture was allowed to warm to room temperature and stirred overnight. Thereaction mixture was diluted with water and extracted into EtOAc(3), and the crude product obtained was recrystallized from anappropriate solvent, unless stated otherwise.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2451 - 2465

46
4-(2-fluorophenyl)thiazol-2-ethylamine hydrobromide [ No CAS ]
[ 1711-11-1 ]
2-[2-(3-cyanobenzamido)]ethyl-4-(2-fluorophenyl)-thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In tetrahydrofuran; at 20℃;	General procedure: A suspension of one of the 4-arylthiazol-2-ethylamine hydrobromides89a-f (1 mmol) in THF (10 mL) was treated with triethylamine(minimum of 2.5 equiv). The appropriate sulfonyl, acyl, orcarbamoyl chloride was added (minimum of 1.1 equiv), and themixture was stirred overnight at room temperature before beingdiluted with water and extracted into EtOAc (3. The productswere recrystallized from EtOAc/hexane unless stated otherwise.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2451 - 2465

47
4-(3-fluorophenyl)thiazol-2-ethylamine hydrobromide [ No CAS ]
[ 1711-11-1 ]
2-[2-(3-cyanobenzamido)]ethyl-4-(3-fluorophenyl)thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In tetrahydrofuran; at 20℃;	General procedure: A suspension of one of the 4-arylthiazol-2-ethylamine hydrobromides89a-f (1 mmol) in THF (10 mL) was treated with triethylamine(minimum of 2.5 equiv). The appropriate sulfonyl, acyl, orcarbamoyl chloride was added (minimum of 1.1 equiv), and themixture was stirred overnight at room temperature before beingdiluted with water and extracted into EtOAc (3. The productswere recrystallized from EtOAc/hexane unless stated otherwise.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2451 - 2465

48
[ 1711-11-1 ]
2-(4-aminophenyl)-5,6,7-trimethoxy-4H-chromen-4-one [ No CAS ]
3-cyano-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate; In acetone; at 20℃;	General procedure: Potassium carbonate (211 mg, 1.53 mmol) was added to a stirred solution of compounds 1a or 1b(0.31 mmol) in acetone (5 mL) at room temperature then further stirred for 5 minutes. Theappropriate benzoyl chloride derivative (0.37 mmol, 1.2 equivalents) was added and stirring wascontinued at ambient temperature until consumption of the starting material. The reaction mixture was diluted with water then extracted with dichloromethane, washed (brine), dried (anhydroussodium sulfate) and evaporated in vacuo. Recrystallization of the crude product afforded the titledcompounds.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4170 - 4173
[2]European Journal of Medicinal Chemistry,2020,vol. 187

49
[ 1467668-53-6 ]
[ 1711-11-1 ]
3-cyano-N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In acetone; at 20℃;	General procedure: Potassium carbonate (211 mg, 1.53 mmol) was added to a stirred solution of compounds 1a or 1b(0.31 mmol) in acetone (5 mL) at room temperature then further stirred for 5 minutes. Theappropriate benzoyl chloride derivative (0.37 mmol, 1.2 equivalents) was added and stirring wascontinued at ambient temperature until consumption of the starting material. The reaction mixture was diluted with water then extracted with dichloromethane, washed (brine), dried (anhydroussodium sulfate) and evaporated in vacuo. Recrystallization of the crude product afforded the titledcompounds.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4170 - 4173
[2]European Journal of Medicinal Chemistry,2020,vol. 187

50
tert-butyl (R)-4-(5-amino-4-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2-dimethylpiperidine-1-carboxylate [ No CAS ]
[ 1711-11-1 ]
tert-butyl (R)-4-(5-(3-cyanobenzamido)-4-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2-dimethylpiperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25℃; for 1h;	To the stirred solution of tert-butyl (R)-4-(5- amino-4-methoxy-1 -methyl-1 H-pyrrolo[2,3-b]pyridin-3-yl)-2,2-dimethylpiperidine-1-carboxylate (240 mg, 0.618 mmol) in DCM (20 mL) was added <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (150 mg, 0.906 mmol) and DIPEA (0.5 mL) at 25 C. The solution was allowed to stir for 1 h, then quenched with water (5 mL) and extracted with DCM (15 mL x 2). The combined organic layers were separated, dried, concentrated and purified by column chromatography (EtOAc:PE 30:70 70%) to give product (260 mg, 81 %) as a light yellow oil. LCMS [M+H] = 518.1 ; 1H NMR (400 MHz, CDCI3) delta 8.93 (s, 1 H), 8.26-8.19 (m, 2 H), 8.07 (s, 1 H), 7.88-7.86 (m, 1 H), 7.69-7.66 (m, 1 H), 6.91 (s, 1 H), 4.05-4.01 (m, 1 H), 3.98 (s, 3 H), 3.85 (s, 3 H), 3.23-3.17 (m, 2 H), 2.21-2.13 (m, 1 H), 1.96-1.88 (m, 1 H), 1.63-1.50 (m, 8 H), 1.49 (s, 9 H).

Reference： [1]Patent: WO2016/120849,2016,A1 .Location in patent: Page/Page column 76

51
[ 1267986-38-8 ]
[ 1711-11-1 ]
[ 1267989-19-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	4-chlorodeacetyl colchicine (50 mg, 0.128 mmol) was dissolved in dichloromethane (2 mL) under argon atmosphere, and cooled at 0 degree C. Triethylamine (19 mul, 0.128 x 1.1 mmol) and 3-cyanobenzoylchloride (21 mg, 0.128 x 1 mmol) were added, and stirred at room temperature for 2 hours. Water was added and reaction mixture was quenched, saturated sodium bicarbonate solution was added, and extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The obtained residue was purified by Silica gel chromatography (Biotage Isolera One and SNAP 10 g, methanol/chloroform) to obtain title compound (a light yellow solid, 44 mg, 0.084 mmol, 66%).

Reference： [1]Patent: JP5829520,2015,B2 .Location in patent: Paragraph 0253

52
4-iododeacetyl colchicine [ No CAS ]
[ 1711-11-1 ]
N-(3-cyanobenzoyl)-4-iododeacetyl colchicine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1.16h;Inert atmosphere;	4-iododeacetyl colchicine (50 mg,0.103 mmol) was dissolved in dichloromethane (2 mL) under argon atmosphere, and cooled at 0 degree C. Triethylamine (16 mul, 0.103 x 1.1 mmol) and 3-cyanobenzoylchloride (17 mg,0.103 x 1 mmol) were added, and stirred at 0 degree C for 10 minutes, and room temperature for 1hour. Water was added and reaction mixture was quenched, and 0.1N hydrochloric acid was added, and extracted with chloroform. The chloroform layer was washed with Saturated sodium bicarbonate solution and a saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The obtained residue was purified by Silica gel column chromatography(Biotage Isolera One, SNAP 10 g, methanol/chloroform) to obtain title compound (a yellow solid, 44 mg, 0.072 mmol, 70%).

Reference： [1]Patent: JP5829520,2015,B2 .Location in patent: Paragraph 0427

53
[ 1711-11-1 ]
3-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With trimethylsilylazide; at 100℃;Sealed tube;	Preparation of 1-(3-cyanophenyl)-1,4-dihydro-5H-tetrazol-5-one 6m A stirred mixture of azidotrimethylsilane (2.4 mL, 18 mmol) and <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (497 mg, 3.0 mmol) was heated from room temperature to 100 C. (block temperature) in a sealed vial with pressure-release cap. The mixture was then stirred at 100 C. overnight (Note: pressure developed during heating). After cooling, the mixture was concentrated under vacuum and the residue partitioned between EtOAc (10 mL) and a saturated aqueous solution of NaHCO3 (10 mL). The organic layer was extracted with a further quantity of saturated aqueous NaHCO3 (110 mL) [note: organic layer was assessed by TLC to ascertain if tetrazolone product was completely removed. If tetrazolone was still present in organic layer, then further extractions with saturated NaHCO3 were used]. EtOAc (20 mL) was added to the combined NaHCO3 layers, and the pH was adjusted to <3 using 6N HCl with efficient stirring. The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (210 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent removed under vacuum to afford the product (505 mg, 90%) as a solid. A sample was recrystallized from EtOAc. 1H NMR (DMSO-d6, 300 MHz): delta 8.26 (m, 1H), 8.16 (ddd, J=8.7, 2.4, 1.2 Hz, 1H), 7.87 (dt, J=7.8, 2.7 Hz, 1H), 7.48 (dt, J=8.3, 0.6 Hz, 1H), -1.1 (br. s, 1H) 13C NMR (DMSO-d6, 75 MHz): delta 150.1, 134.9, 131.1, 131.0, 123.7, 122.1, 117.9, 112.4 m/z=188.30 [M+H]+ and 186.42 [M-H]+ HRMS (EI): [M-H]+ calc'd for C8H5N5O m/z 186.0486. found 186.0427.

Reference： [1]Patent: US2016/213648,2016,A1 .Location in patent: Paragraph 0323; 0324; 0325; 0326; 0327; 0328

54
[ 38291-82-6 ]
[ 1711-11-1 ]
C₁₃H₁₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In tetrahydrofuran; at 20℃; for 1h;	At first, m-cyano benzoic acid chloride (1.4 g) was added with THF (20 mL), was added with a mixture of THF (15 mL), triethyl amine (1.3 mL) and butyric acid hydrazide (1.0 g), which was prepared according to the method described in J. Med. Chem. 2001, 44, 1268, and was stirred at the room temperature for an hour. The mixture was added with 200 mL of ethyl acetate, was washed with dilute hydrochloric acid, saturated sodium bicarbonate water and saturated salt solution, was dried, and was condensed to give 1.7 g (81% yield constant) of a hydrazine derivative.

Reference： [1]Patent: US9481658,2016,B2 .Location in patent: Paragraph 98; 99

55
[ 1711-11-1 ]
[ 71-36-3 ]
C₁₂H₁₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In tetrahydrofuran; at 20℃; for 2h;	At first, m-cyano benzoic acid chloride (2 g) was added with THF (20 mL), was added with a mixture of THF (15 mL), triethyl amine (2.6 mL) and n-butanol (1.7 mL), and was stirred at the room temperature for two hours. The mixture was added with 200 mL of ethyl acetate, was washed with dilute hydrochloric acid, saturated sodium bicarbonate water and saturated salt solution, was dried, and was condensed to give 2.4 g (96% yield constant) of a butyl ester derivative.

Reference： [1]Patent: US9481658,2016,B2 .Location in patent: Paragraph 99; 100

56
[ 110-63-4 ]
[ 1711-11-1 ]
4-hydroxybutyl 3-cyanobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine; In dichloromethane; at 0 - 25℃; for 1.16667h;	A solution of <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (660 mg, 4 mmol) in DCM (5 mL) was added dropwise during 10 mm to a stirred solution of butane-1,4-diol (450 mg, 5 mmol ) and Et3N (505 mg, 5 mmol) in DCM (5 mL) at 0 C. The reaction was allowed to warm up gradually and stirred at 0 - 25 C for over 1 h. After that, the reaction mixture was diluted with H20 (5 mL) and stirred for 5 mm. The aqueous phase was separated and extracted with DCM (5 mL). The combined organic phase was washed with saturated brine (5 mL), dried over anhydrous Na2SO4 and evaporated. The residue was purified by a silica gel flash column with Hex/EA = 10:1-5:1 to yield the titled compound (450 mg, 51%) as a colorless oil. ?H NMR was performed at 400IVIHz with CDC13 as solvent to characterize the titled compound, results are as follows: = 8.31 (s, 1 H), 8.26 (d, J = 8.0 Hz, 1 H), 7.83 (d, J = 7.6 Hz, 1 H), 7.58 (t, J = 8.0 Hz, 1 H), 4.39 (t, J = 6.4 Hz, 2 H), 3.73 (t, J = 6.4 Hz, 2 H), 1.92 - 1.85 (m, 2 H), 1.76 - 1.69 (m, 2 H).

Reference： [1]Patent: WO2017/49470,2017,A1 .Location in patent: Paragraph 00141; 00142

57
[ 442-16-0 ]
[ 1711-11-1 ]
N-(9-amino-2-ethoxyacridin-6-yl)-3-cyanobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	4 Typical procedure for 3-amide derivatives: Synthesis of N-(9-amino-2-ethoxyacridin-6-yl)benzamide (7) General procedure: Benzoyl chloride (50.0μL, 0.594mmol) was added to a mixture of 26a (100mg, 0.396mmol) and pyridine (3 drops) in DMF (4mL) under an Ar atmosphere. The mixture was stirred at room temperature overnight, and then poured into water (20mL). The resulting yellow precipitate was collected by filtration, washed with hot water and ethyl acetate, and dried in vacuo to yield 7 (62.2mg, 42%) as a yellow powder, which was purified by recrystallization from DMSO/methylene chloride. Mp 279°C (dec); 1H NMR (400MHz, DMSO-d6) δ 10.5 (1 H, s), 8.37 (1 H, s), 8.33 (1 H, d, J=9.3Hz), 8.01 (2 H, m), 7.73 (1 H, d, J=9.3Hz), 7.68-7.55 (7 H, m), 7.35 (1 H, 9.2Hz), 4.18 (2 H, q, J=7.0Hz), 1.43 (3H, t, J=7.0Hz); 13C NMR (125MHz, DMSO-d6) δ 166.0, 153.4, 148.5, 147.5, 144.8, 139.8, 135.0, 131.7, 129.4, 128.5, 127.8, 124.0, 123.4, 117.3, 115.5, 112.9, 109.6, 101.3, 63.6, 14.7; HRMS (ESI+) calcd for C22H20N3O2 (M+H)+ 358.1550. found 358.1552.

Reference： [1]Ishigami-Yuasa, Mari; Watanabe, Yuko; Mori, Takayasu; Masuno, Hiroyuki; Fujii, Shinya; Kikuchi, Eriko; Uchida, Shinichi; Kagechika, Hiroyuki [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3845 - 3852]

58
⁴^{-(7-methylbenzo[d]oxazol-2-yl)aniline} [ No CAS ]
[ 1711-11-1 ]
3-cyano-N-[4-(7-methyl-2-benzoxazolyl)phenyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		7-Methyl-2- (4-aminophenyl) benzoxazole (19.9 mg, 0.0888 mmol) was dissolved in anhydrous tetrahydrofuran (500 muL) 60% sodium hydride (14.2 mg, 0.339 mmol) was added under an argon atmosphere, and after stirring at room temperature for 5 minutes, <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (14.7 mg, 0.0888 mmol) was added and the mixture was stirred at room temperature for 12 hours. After completion of the reaction was confirmed by TLC, a saturated ammonium chloride aqueous solution (5 mL) was poured into the reaction suspension, and shaking extraction with ethyl acetate (10 × 2 mL) was performed. Further, the ethyl acetate layer was washed with water (10 mL), saturated aqueous sodium chloride solution (10 mL), dried over anhydrous sodium sulfate, dried and filtered, and then the solvent was distilled off.The precipitated solid was resuspended in ethyl acetate: hexane = 1: 4 solution (5 mL), collected by filtration, washed with the same solvent (10 mL) After rinsing with water (10 mL), the residue was dried under reduced pressure to obtain 23.9 mg (0.0677 mmol, yield 76%) of the title compound as white crystals.

Reference： [1]Patent: JP2018/87173,2018,A .Location in patent: Paragraph 0158-0159

59
[ 20934-81-0 ]
[ 1711-11-1 ]
3-cyano-N-[4-(2-benzoxazolyl)phenyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		2- (4-aminophenyl) benzoxazole (50 mg, 0.238 mmol) was dissolved in anhydrous tetrahydrofuran (5 mL)60% sodium hydride (19.2 mg, 0.476 mmol) was added under an argon atmosphere and stirred at room temperature for 10 minutes, then <strong>[1711-11-1]3-cyanobenzoyl chloride</strong> (39.7 mg, 0.238 mmol) was added dropwise, For 30 minutes.After the reaction, a saturated ammonium chloride aqueous solution (5 mL) was poured into the reaction suspension, and shaking extraction with ethyl acetate (5 × 2 mL) was performed. Further, the ethyl acetate layer was washed with water (10 mL), saturated aqueous sodium chloride solution (10 mL), dried over anhydrous sodium sulfate, dried and filtered, and then the solvent was distilled off. The precipitated solid was resuspended in a 1: 4 ethyl acetate: hexane solution (5 mL), collected by filtration, washed with the same solvent (10 mL) and then dried under reduced pressure to give the title compound as pale yellow crystals 63.1 mg (0.186 mmol, yield 77%) was obtained.

Reference： [1]Patent: JP2018/87173,2018,A .Location in patent: Paragraph 0179-0180

60
[ 4414-89-5 ]
[ 1711-11-1 ]
1-(3-cyanobenzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With triethylamine; In dichloromethane; at 0 - 20℃; for 4h;	General procedure: To a cooled (0 C) suspension of 1a-h20-26 (0.56 mmol) in anhydrousCH2Cl2 (2 mL), 0.72 mmol Et3N and 1.67 mmol of the appropriatechloride were added. The mixture was stirred at 0 C for 2 h and then atroom temperature for an additional 2 h. The solvent was evaporated,cold water was added, and the mixture was neutralized with 0.5 NNaOH. The reaction mixture was extracted with CH2Cl2 (3×15 mL),the solvent was dried over sodium sulfate, evaporated in vacuo, and thefinal compounds were purified by crystallization from ethanol (2a-i,3a,b,e, and 4b) or by column chromatography using cyclohexane/ethylacetate in different ratios: 1:1 (3d), 2:1 (3c and 4a), 3:1 (2l, 4b, 5a and5e), 5:1 (5c), or 6:1 (5b and 5d) as eluents

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5583 - 5595

61
[ 103907-17-1 ]
[ 1711-11-1 ]
3-cyano-N-(5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		General procedure: The appropriate acyl chloride (2.5 equiv) was added dropwise to a solution of triazolo[1,5-a]pyrimidin-2-amine 11 or 12 or triazolo[1,5-a]pyridin-2-amine 16 (1 equiv) in pyridine at 0 C. The reaction mixture was allowed to warm up to r.t. and stirred for 1-2 h. EtOAc was added, and the organic layer was washed with HCl 1N (2 X), followed by water or brine. After solvent evaporation, the resultant residue was treated with 7 N methanolic ammonia solution and stirred at r.t. overnight to hydrolyze any potential bis-acylated product formed. The product was then purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 - 10%) in DCM or MeOH (0 - 5%) in DCM, washed with MeOH and dried in vacuum to afford the desired compound (adapted from 1).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 257 - 261

62
[ 1711-11-1 ]
[ 52568-28-2 ]
3-cyano-N-(2-(pyridin-2-yl)propan-2-yl)benzamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 2645 - 2649

63
[ 3250-74-6 ]
[ 1711-11-1 ]
[ 1022089-84-4 ]

Reference： [1]Acta Crystallographica Section C: Structural Chemistry,2019,vol. 75,p. 1327 - 1335

64
[ 599-61-1 ]
[ 1711-11-1 ]
C₂₈H₁₈N₄O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In dichloromethane; water; at 20℃;	General procedure: All materials, reagents and solvents were purchased fromSigma-Aldrich, Merck, and Tedia Brazil and were used as received.The classical Schotten-Baumann reaction was used for the synthesisof amides [23-25]. Typical procedure: A solution of the acylchloride (0.5 mmol) in dichloromethane (2 mL) was added dropwiseto a well-stirred mixture of the aniline (0.5 mmol) indichloromethane (2 mL) and 2 mL of aqueous sodium carbonate(10%) at room temperature. The reaction media was stirred for90 min and then the organic phase was separated and extractedwith brine (3 x 2 mL). The combined organic fractions were dried over MgSO4, filtered, and evaporated to dryness under reducedpressure to give the N-phenylbenzamides in 19-90% yields. Onehundred and seventeen compounds were synthesized followingthis procedure. Detailed physicochemical properties, 1H and 13CNMR data, FT-IR data, and yield are presented for each N-phenylbenzamidein the supplementary data.

Reference： [1]Journal of Molecular Structure,2020,vol. 1208

65
[ 593-51-1 ]
[ 1711-11-1 ]
[ 363186-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; for 8h;

Reference： [1]Ackermann, Lutz; Struwe, Julia; Zhang, Yan [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 15076 - 15080][Angew. Chem.]

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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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1711-11-1 ] {[proInfo.proName]}

Quality Control of [ 1711-11-1 ]

Related Doc. of [ 1711-11-1 ]

Product Details of [ 1711-11-1 ]

Calculated chemistry of [ 1711-11-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1711-11-1 ]

Application In Synthesis of [ 1711-11-1 ]

[ 1711-11-1 ] Synthesis Path-Upstream 1~5

[ 1711-11-1 ] Synthesis Path-Downstream 1~65

Related Functional Groups of [ 1711-11-1 ]

Aryls

Chlorides

Acyl Chlorides

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 1711-11-1 ]