[ CAS No. 366-84-7 ]

Name: 366-84-7|Ethyl 4-(aminomethyl)benzoate|95%
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Quality Control of [ 366-84-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 366-84-7 ]

Product Details of [ 366-84-7 ]

CAS No. :	366-84-7	MDL No. :	MFCD00748342
Formula :	C₁₀H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WCTQEHGXBKFLKG-UHFFFAOYSA-N
M.W :	179.22	Pubchem ID :	436161
Synonyms :

Calculated chemistry of [ 366-84-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.2
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	1.5
Log Po/w (WLOGP) :	1.17
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	1.67
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.97
Solubility :	1.9 mg/ml ; 0.0106 mol/l
Class :	Very soluble
Log S (Ali) :	-2.21
Solubility :	1.11 mg/ml ; 0.00622 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.92
Solubility :	0.214 mg/ml ; 0.00119 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.35

Safety of [ 366-84-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 366-84-7 ]

* 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 [ 366-84-7 ]
Downstream synthetic route of [ 366-84-7 ]

[ 366-84-7 ] Synthesis Path-Upstream 1~9

1
[ 366-84-7 ]
[ 56-91-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 80℃; for 1 h;	2) adding ethyl 4-aminomethylbenzoate to the concentrated sulfuric acid solution,The molar ratio of sulfuric acid to 4-aminomethylalkyl benzoate is 2:1,The reaction was stirred at 80 ° C for 1 h, and after completion of the reaction, it was cooled to room temperature.Add water (the amount of water is 20 times the amount of methyl 4-aminomethylbenzoate), then add ammonia water dropwise to the solution to make the solution alkaline.There is a lot of solids to precipitate, filter, wash,Drying gave a white solid aminotoluic acid.

Reference： [1] Patent: CN108623488, 2018, A, . Location in patent: Paragraph 0040; 0042; 0043; 0045; 0046; 0048; 0053

2
[ 56-91-7 ]
[ 64-17-5 ]
[ 366-84-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 20℃; for 4.5 h; Cooling with ice; Reflux	Example 1 Preparation of p-aminomethylbenzoic acid ethyl ester In 250mL neck round bottom flask was added 7.5g (50mmol) p-aminomethylbenzoic acid. Added with 100mL anhydrous ethanol. In an ice bath, was slowly added thionyl chloride 20.8g (175mmol), after the addition was complete, stirring at room temperature after 30min, was heated at reflux for 4h. After stopping the heating, removal of the ethanol under reduced pressure to give a white solid. The solid was dissolved with 150mL ethyl acetate in an ice bath was slowly added 35percent NaOH aqueous solution to pH 7-8. Still stratification, washed three times with saturated saline aqueous layer was removed, and the organic layer, each 30mL. Dried over anhydrous sodium sulfate, filtered, and concentrated to give a yellow solid, 90percent yield.

Reference： [1] Patent: CN104016942, 2016, B, . Location in patent: Paragraph 0090; 0091; 0092
[2] Journal of the American Chemical Society, 1943, vol. 65, p. 2281,2283
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6023 - 6028
[4] Journal of the American Society for Mass Spectrometry, 2018, vol. 29, # 4, p. 694 - 703

3
[ 1201-90-7 ]
[ 366-84-7 ]

Reference： [1] Patent: CN108623488, 2018, A, . Location in patent: Paragraph 0040; 0041; 0046; 0047

4
[ 26496-94-6 ]
[ 366-84-7 ]

Reference： [1] Patent: CN108623488, 2018, A, . Location in patent: Paragraph 0043; 0044

5
[ 7153-22-2 ]
[ 366-84-7 ]

Reference： [1] Inorganic Chemistry, 2018, vol. 57, # 24, p. 15069 - 15078
[2] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 257,258
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 2514

6
[ 64-17-5 ]
[ 2393-20-6 ]
[ 366-84-7 ]

Reference： [1] Patent: CN108794492, 2018, A, . Location in patent: Paragraph 0060; 0061

7
[ 56-91-7 ]
[ 366-84-7 ]

Reference： [1] Patent: EP976722, 2000, A1,

8
[ 56-91-7 ]
[ 366-84-7 ]

Reference： [1] Patent: US5834468, 1998, A,

9
[ 7153-22-2 ]
[ 366-84-7 ]
[ 131065-88-8 ]

Reference： [1] Helvetica Chimica Acta, 1930, vol. 13, p. 457,470

[ 366-84-7 ] Synthesis Path-Downstream 1~69

1
[ 7153-22-2 ]
[ 366-84-7 ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 15069 - 15078
[2]Recueil des Travaux Chimiques des Pays-Bas,1947,vol. 66,p. 257,258
[3]Patent: DE518211,1928,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 17,p. 2514

2
[ 7153-22-2 ]
[ 366-84-7 ]
[ 131065-88-8 ]

Reference： [1]Helvetica Chimica Acta,1930,vol. 13,p. 457,470

3
[ 366-84-7 ]
4-[(<i>N</i>'-phenyl-thioureido)-methyl]-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1930,vol. 13,p. 457,470

4
[ 366-84-7 ]
[ 35008-93-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1971,vol. 7,p. 2440 - 2442
Zhurnal Organicheskoi Khimii,1971,vol. 7,p. 2350 - 2352

5
[ 40493-18-3 ]
[ 366-84-7 ]
4-[(5,6,7,8-Tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ylamino)-methyl]-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Pharmazie,1993,vol. 48,p. 585 - 587

6
[ 366-84-7 ]
[ 122283-76-5 ]
[ 122283-75-4 ]

Reference： [1]Zeitschrift fur Chemie,1990,vol. 30,p. 248 - 249

7
[ 366-84-7 ]
[ 109343-21-7 ]
[ 109343-18-2 ]

Reference： [1]Pharmazie,1990,vol. 45,p. 827 - 829

8
[ 366-84-7 ]
[ 85716-85-4 ]
[ 109315-54-0 ]

Reference： [1]Pharmazie,1990,vol. 45,p. 827 - 829

9
[ 366-84-7 ]
[ 109315-58-4 ]
[ 109315-52-8 ]

Reference： [1]Pharmazie,1990,vol. 45,p. 827 - 829

10
[ 366-84-7 ]
[ 130832-72-3 ]
[ 130832-81-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 1161 - 1166
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 1345 - 1351
[2]Pharmaceutical Chemistry Journal,1992,vol. 26,p. 430 - 432

11
[ 366-84-7 ]
[ 152438-35-2 ]
[ 152438-44-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1079 - 1090

12
[ 366-84-7 ]
[ 152438-35-2 ]
N,N-bis(Boc-Tra-Phe-CH₂)-4-ethoxycarbonylbenzylamine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1079 - 1090

13
[ 366-84-7 ]
[ 152465-45-7 ]
N,N-bis(Boc-Tra-Tyr(Z)-CH₂)-4-ethoxycarbonylbenzylamine [ No CAS ]
[ 152438-46-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1079 - 1090

14
[ 108-31-6 ]
[ 366-84-7 ]
4-[((Z)-3-Carboxy-acryloylamino)-methyl]-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1998,vol. 32,p. 581 - 583

15
[ 366-84-7 ]
H-Tra-Phe-4-ethoxycarbonylbenzylaminomethyl ketone dihydrochloride [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1079 - 1090

16
[ 366-84-7 ]
N,N-bis-(H-Tra-Phe-CH₂)-4-ethoxycarbonylbenzylamine dihydrochloride [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1079 - 1090

17
[ 366-84-7 ]
N,N-bis(H-Tra-Phe-CH₂)-4-ethoxycarbonylbenzylamine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1079 - 1090

18
[ 366-84-7 ]
[ 102212-80-6 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1099 - 1113

19
[ 366-84-7 ]
[ 109827-30-7 ]

Reference： [1]Pharmazie,1990,vol. 45,p. 827 - 829

20
[ 366-84-7 ]
[ 35009-08-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1971,vol. 7,p. 2440 - 2442
Zhurnal Organicheskoi Khimii,1971,vol. 7,p. 2350 - 2352

21
[ 58777-65-4 ]
[ 366-84-7 ]
[ 660399-71-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With triethylamine; In dichloromethane; at 20℃; for 17h;	To a solution of [1.] 12 g of the compound obtained in the preceding step in 10 ml of dichloromethane were added 1.06 g (2 [EQ)] of ethyl 4-(aminomethyl) benzoate and 1.04 ml of triethylamine (1.5 eq). The reaction mixture was stirred at room temperature for 17 hours. 50 ml of Water was then added and the solution was successively washed with [1.] ON HCl and a saturated aqueous solution of sodium hydrogenocarbonate. The organic layer was dried over [NA2S04] and concentrated. The residue was purified on a silica gel column with 72: 25 cyclohexane : ethyl acetate to yield 0.76 g (44%) of the desired compound. N. M. [R'H (CDC13) 8] (ppm): 8,0 (m, 2H), 7,4 (m, 4H), 6,4 (bs, 1H), 4,6 (d, 2H), 4,3 (q, 2H), 1,40 (t, 3H).
7%	With triethylamine; In dichloromethane; at 20℃; for 17h;	0.700 g (1.05 equivalents) of the product obtained in Preparation 16 and 0.77 ml of triethylamine (1.5 equivalents) are added to a solution of 0.833 g of the product obtained in the preceding Stage 1 in 15 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 17 hours. The solution is hydrolysed with water and washed with a 1.0M aqueous hydrochloric acid solution and then with a saturated sodium hydrogencarbonate solution. The organic phase is dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate: 97/3) to produce 0.1 g of the expected product. Yield: 7% 1H NMR (CDCl3) delta (ppm): 8.0 (m, 2H), 7.4 (m, 4H), 6.4 (bs, 1H), 4.6 (d, 2H), 4.3 (q, 2H), 1.40 (t, 3H)

Reference： [1]Patent: WO2004/14381,2004,A2 .Location in patent: Page/Page column 39-40
[2]Patent: US2004/72871,2004,A1 .Location in patent: Page/Page column 20

22
[ 366-84-7 ]
[ 121124-94-5 ]
ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)-aminomethyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In ethanol;	2-Benzyloxy-5-bromobenzaldehyde and <strong>[366-84-7]ethyl 4-aminomethylbenzoate</strong> were heated together at 100 C. for 1 hour. The mixture was cooled, dissolved in ethanol (100 ml) and sodium borohydride (1.3 g) was added. The mixture was stirred for 18 hours at ambient temperature, acidified with acetic acid and water (200 ml) was added. The mixture was extracted with diethyl ether (4*100 ml), the extracts washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate which was purified by chromatography on silica gel eluding with CH2 Cl2 then 5% ethyl acetate/CH2 Cl2 (yield 11.4 g).

Reference： [1]Patent: US5834468,1998,A

23
[ 56-91-7 ]
4-[N-(2-Benzyloxy-5-bromobenzyl)aminomethyl]benzoic acid [ No CAS ]
[ 366-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	A mixture of 4-aminomethylbenzoic acid (25 g) and concentrated sulphtiric acid (25 ml) in ethanol (250 ml) was heated at reflux for 18 hours. The volume of solvent was reduced to a third by evaporation. The residue poured onto ice (500 g) and basified with concentrated aqueous ammonia. The product was extracted with ethyl acetate (3*200 ml) and the extracts dried and evaporated to give ethyl 4-aminomethylbenzoate.

Reference： [1]Patent: US5834468,1998,A

24
[ 366-84-7 ]
[ 13091-23-1 ]
ethyl 4-[[(3-nitro-4-pyridyl)amino]methyl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(a) 4-(4-Ethoxycarbonylbenzylamino)-3-nitropyridine STR77 The title compound, m.p. 166-8, was prepared by the method of Preparation 16(a) using <strong>[366-84-7]ethyl 4-aminomethylbenzoate</strong> and 4-chloro-3-nitropyridine as the starting materials. Analysis %: Found: C,59.45; H,4.97; N,13.54; C15 H15 N3 O4 requires: C,59.8; H,4.98; N,13.95.

Reference： [1]Patent: US4904671,1990,A

25
[ 24424-99-5 ]
[ 366-84-7 ]
[ 157311-42-7 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2 Synthesis of ethyl 4-[(t-butoxycarbonylamino)methyl]benzoate: The title compound was obtained from <strong>[366-84-7]ethyl 4-(aminomethyl)benzoate</strong> and di-t-butyl dicarbonate in the same manner as that of step 1 in Example 1. H-NMR (CDCl3) delta 1.45 (9H, s), 4.36 (2H, d), 4.36 (2H, q), 4.90 (1H, br), 7.35 (2H, d), 8.00 (2H, d)

Reference： [1]Patent: EP976722,2000,A1

26
[ 56-91-7 ]
[ 366-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol;	Step 1 Synthesis of ethyl 4-(aminomethyl)benzoate: 3 g (19.9 mmol) of 4-aminomethylbenzoic acid was suspended in 100 ml of ethanol. 10 ml of ethanol containing 25 % of hydrogen chloride was added to the suspension, and they were heated under reflux for 8 hours. The solvent was evaporated, and the title compound was obtained by the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant. Yield: 1.19 g (6.77 mmol) (34 %) H-NMR (CDCl3) delta 1.35 (3H, t), 4.05 (2H, brs), 4.30 (2H, q), 6.60 (2H, d), 7.85 (2H, d)

Reference： [1]Patent: EP976722,2000,A1

27
[ 366-84-7 ]
[ 1256150-75-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 4716 - 4719

28
[ 1228362-38-6 ]
[ 366-84-7 ]
[ 1228362-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In toluene; for 5h;Reflux;	Example 23Ethyl 4-(2,6-dimethyl-5-[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)benzoateA mixture of 4-chloro-2,6-dimethyl-5-[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine (5.0 g), ethyl (4-aminomethyl)benzoate (3.8 g), triethylamine (2.8 ml) and toluene (150 ml) was heated to reflux while stirring for 5 hours. The mixture thus obtained was concentrated under reduced pressure. To the resultant residue, water was added. After extraction was performed with chloroform, an organic phase was dried over anhydrous sodium sulfate and evaporated. The evaporation residue was purified by column chromatography to obtain a target substance (1 g). The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.Mass spectrum: 454.

Reference： [1]Patent: US2011/319618,2011,A1 .Location in patent: Page/Page column 24

29
[ 366-84-7 ]
[ 92289-43-5 ]
[ 1378233-17-0 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2814 - 2817

30
[ 366-84-7 ]
[ 530-62-1 ]
[ 1378233-02-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2814 - 2817

31
[ 366-84-7 ]
[ 470715-75-4 ]
[ 1378233-13-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2814 - 2817

32
[ 366-84-7 ]
[ 33876-92-5 ]
[ 1378233-18-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2814 - 2817

33
[ 366-84-7 ]
[ 6287-86-1 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 1155 - 1160

34
[ 366-84-7 ]
[ 1452303-73-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6023 - 6028

35
[ 366-84-7 ]
C₃₀H₄₃NO₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6023 - 6028

36
[ 366-84-7 ]
[ 1452303-57-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6023 - 6028

37
[ 17610-00-3 ]
[ 366-84-7 ]
[ 1452303-55-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6023 - 6028

38
[ 366-84-7 ]
[ 141-78-6 ]
[ 20686-41-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2018 - 2021

39
C₁₅H₉ClN₂O [ No CAS ]
[ 366-84-7 ]
[ 1581275-68-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2413 - 2428

40
[ 366-84-7 ]
[ 30562-34-6 ]
[ 1622011-62-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 24h;	General procedure: To geldanamycin (34 mg, 0.06 mmol, 1.0 equiv.) in dichloromethane (8 mL) was added substitutional arylmethylamine (0.12 mmol, 20.0 equiv.). The reaction mixture was stirred for 24 h at room temperature, and the color changed from yellow to purple. TLC was used to monitor the progress of the reaction. After the reaction complete, the mixture was diluted with 20 mL of dichloromethane and washed with 1.5 N HCl (2 x 20 mL) followed by brine (3 x 25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The residue was purified by flash column chromatography (silica gel, ethyl acetate/petroleum ether 1:1) to afford a purple solid.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 85,p. 359 - 370

41
[ 366-84-7 ]
4-(3-fluorobenzoylaminomethyl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2015/7870,2015,A1
[2]Patent: EP2826769,2015,A1
[3]International Journal for Parasitology: Drugs and Drug Resistance,2018,vol. 8,p. 59 - 66

42
[ 366-84-7 ]
4-[(3-fluorophenyl)formamido]methyl}-N-hydroxybenzamide [ No CAS ]

Reference： [1]Patent: WO2015/7870,2015,A1
[2]Patent: EP2826769,2015,A1
[3]International Journal for Parasitology: Drugs and Drug Resistance,2018,vol. 8,p. 59 - 66

43
[ 366-84-7 ]
[ 1711-07-5 ]
4-(3-fluorobenzoylaminomethyl)benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 40℃;	Amine derivative la or l b (1 eq.) was dissolved in dry DCM (0.2M). Triethylamine (3 eq.) and the acid chloride or sulfonyl chloride (1 eq.) were added successively and the reaction mixture was heated at 40C. After the reaction was complete (TLC control), the reaction mixture was concentrated. The residue was taken up with EtOAc and the organic phase was washed with a solution of 1 M HC1, a saturated solution of NaHC03 and brine, dried over Na2S04, filtrated and concentrated to afford 2a-2h. The products were used such as in the next step.
	With triethylamine; In dichloromethane; at 40℃;	General procedure: Amine derivative 1a or 1b (1 eq.) was dissolved in dry DCM (0.2M). Triethylamine (3 eq.) and the acid chloride or sulfonyl chloride (1 eq.) were added successively and the reaction mixture was heated at 40C. After the reaction was complete (TLC control), the reaction mixture was concentrated. The residue was taken up with EtOAc and the organic phase was washed with a solution of 1M HCl, a saturated solution of NaHCO3 and brine, dried over Na2SO4, filtrated and concentrated to afford 2a-2h. The products were used such as in the next step.

Reference： [1]Patent: WO2015/7870,2015,A1 .Location in patent: Page/Page column 24
[2]Patent: EP2826769,2015,A1 .Location in patent: Paragraph 0063
[3]International Journal for Parasitology: Drugs and Drug Resistance,2018,vol. 8,p. 59 - 66

44
[ 40663-68-1 ]
[ 366-84-7 ]
C₂₀H₂₃NO₃ [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 42713 - 42719

45
[ 366-84-7 ]
C₂₅H₃₁NO₅ [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 42713 - 42719

46
[ 366-84-7 ]
C₃₀H₃₀N₄O₆ [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 42713 - 42719

47
[ 366-84-7 ]
(Z)-3-(2-(6-chloro-1-(4-fluorobenzyl)-1H-indol-3-yl)-1-cyanovinyl)benzoic acid [ No CAS ]
C₃₅H₂₇ClFN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃;	j00380j 3 -[(Z)-2-( 1 -benzyl-6-chloro-indol-3 -yl)-l -cyano-vinyl]benzoic acid (Intermediate B) (20 mg, 0.046 mmol) was dissolved in CH2C12 (4 mL). To the mixture was then added HATU (17 mg, 0.046 mmol), followed by <strong>[366-84-7]ethyl 4-(aminomethyl)benzoate</strong> (8 mg. 0.046 mmol) and DIEA (16 tL, 0.092 mmol). The mixture was stirred at room temperature overnight. The solvents were evaporated to dryness and the crude then purified over silica gel, 0-100% EtOAc in hexanes to afford the desired intermediate (Compound 1-1 ethyl ester). The ester was then dissolved in a mixture of THF (4mL), MeOH (2 mL) and H20 (1 mL). To the mixture was added 1 eq. of iN NaOH. The mixture was stirred at room temperature. After completion of the reaction, the mixture was evaporated to dryness to afford the title compound 1-1 as the sodium salt (20 mg, 74%) as a yellow solid. LC-MS: m/z 564 (M+1).

Reference： [1]Patent: WO2016/144704,2016,A2 .Location in patent: Paragraph 00380

48
[ 366-84-7 ]
(Z)-3-(2-(6-chloro-1-(4-fluorobenzyl)-1H-indol-3-yl)-1-cyanovinyl)benzoic acid [ No CAS ]
(Z)-4-((3-(2-(6-chloro-1-(4-fluorobenzyl)-1H-indol-3-yl)-1-cyanovinyl)benzamido)methyl)benzoic acid sodium salt [ No CAS ]

Reference： [1]Patent: WO2016/144704,2016,A2

49
[ 366-84-7 ]
[ 100-52-7 ]
[ 68-11-1 ]
2-phenyl-3-(4-ethoxycarbonylbenzyl)-4-thiazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20℃; for 3h;	Example 2 Preparation of 2-phenyl-3-(4-ethoxycarbonylbenzyl)-4-thiazolidinone The 8.26g (50mmol) of p-aminomethylbenzoic acid (prepared as in Example 1) was dissolved in 300mLTHF. After addition of 10.61g (100mmol) benzaldehyde was placed under the ice bath and was added dropwise 7.00mL (100mmol) thioglycolic acid then was added with portionwise 12.40g (60mmol) DCC. At room temperature, the reaction is for 3h. After stopping the reaction, the reaction system was filtered off white solid (the DCU, DCC and water to the product after the reaction). Then the system was removed with THF by distillation under reduced pressure to give a white solid. After, the solid was dissolved with 300mL ethyl acetate, then the organic layer was washed successively with 5% aqueous citric acid solution, distilled water, 5% aqueous sodium bicarbonate solution and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a white solid. Finally recrystallized with anhydrous ethanol. 90% yield as a white solid, mp: 149.2-151.0 .

Reference： [1]Patent: CN104016942,2016,B .Location in patent: Paragraph 0093; 0094; 0095; 0096
[2]Journal of Biomolecular Structure and Dynamics,2019

50
[ 366-84-7 ]
C₁₃H₁₉NO₂ [ No CAS ]

Reference： [1]Patent: CN105541751,2016,A

51
[ 366-84-7 ]
benzamide, N-[5-[[5-[(4-acetyl-1-piperazinyl)carbonyl]-4-methoxy-2-methylphenyl]thio]-2-thiazolyl]-4-[[(1,2-dimethylpropyl)amino]methyl] [ No CAS ]

Reference： [1]Patent: CN105541751,2016,A

52
[ 563-80-4 ]
[ 366-84-7 ]
C₁₅H₂₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Three 100mL flask was added ethanol 50mL, Compound IV-1 (5g, 28mmol, 1eq), Compound SM-2 (7.2g, 84mmol, 3eq), acetic acid (0.08g, 1.4mmol, 0.05eq) and 4A molecular sieves (2g ), And the reaction solution was stirred at 25 to 30 C for 3 hours. NaBH4 (1.6 g, 42 mmol, 1.5 eq) was added in three batches and the reaction was carried out at 20 to 30 C for 16 hours. The reaction solution was filtered and the filtrate was concentrated to dryness. The reaction solution was dissolved in water (100 mL) and adjusted to pH 8-9 by addition of NaOH (3.0 M). The organic phase was combined, dried and concentrated to give the crude product of compound III-2 as a light yellow liquid (6.6 g) which was used directly in the next step.

Reference： [1]Patent: CN105541751,2016,A .Location in patent: Paragraph 0070; 0071; 0072

53
[ 366-84-7 ]
2-(9H-pyrido[3,4-b]indole-9-yl)acetic acid [ No CAS ]
C₂₃H₂₁N₃O₃ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1457 - 1466

54
[ 701-27-9 ]
[ 366-84-7 ]
C₁₆H₁₆FNO₄S [ No CAS ]