[ CAS No. 1643-16-9 ] {[proInfo.proName]}

Name: 1643-16-9|2-(4-Isopropylphenoxy)acetic acid|98%
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Quality Control of [ 1643-16-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1643-16-9 ]

Product Details of [ 1643-16-9 ]

CAS No. :	1643-16-9	MDL No. :	MFCD00014364
Formula :	C₁₁H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FPVCSFOUVDLTDG-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	137131
Synonyms :

Calculated chemistry of [ 1643-16-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.09
TPSA :	46.53 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) :	-5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.69
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	1.96
Log Po/w (SILICOS-IT) :	2.11
Consensus Log Po/w :	2.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.79
Solubility :	0.314 mg/ml ; 0.00161 mol/l
Class :	Soluble
Log S (Ali) :	-3.32
Solubility :	0.093 mg/ml ; 0.000479 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.74
Solubility :	0.351 mg/ml ; 0.00181 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.51

Safety of [ 1643-16-9 ]

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

Application In Synthesis of [ 1643-16-9 ]

* 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 [ 1643-16-9 ]
Downstream synthetic route of [ 1643-16-9 ]

[ 1643-16-9 ] Synthesis Path-Upstream 1~6

1
[ 14062-21-6 ]
[ 1643-16-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: With sodium hydroxide; water In methanol at 20℃; for 3 h; Stage #2: With hydrogenchloride In methanol; water	To a solution of 4-isopropylphenol (1. 007g, 7.39 mmol) in 15 mL DIMETHYLFORMAMIDE was added potassium carbonate (2.04g, 14.79 mmol) and ethyl bromoacetate (1.23 mL, 11.09 MMOL). The reaction was stirred for 48 h at ambient temperature. The mixture was diluted with 500 mL water and extracted with diethyl ether (2 x 200 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 10percent ethyl acetate/hexanes to yield 1. 61G (98percent) of ETHYL- (4-ISOPROPYLPHENOXY) acetate as a clear oil. MS (APCI) 223.3 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.14 (d, 2H), 6.84 (d, 2H), 4.59 (s, 2H), 4.27 (q, 2H), 2.86 (m, 1H), 1.30 (t, 3H), 1.21 (d, 6H). A mixture of ETHYL- (4-ISOPROPYLPHENOXY) acetate (1.61g, 7.24 mmol) and 2N NaOH (aq) (10.9 mL) in 20 mL of methanol was stirred at ambient temperature for 3 h and concentrated under reduced pressure. The resulting residue was taken up in water (100 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2 x 100 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 1. 32G (94percent) of 4-isopropylphenoxyacetic acid as a white solid. MS (APCI) 195.3 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.17 (d, 2H), 6.86 (d, 2H), 4.66 (s, 2H), 2.87 (m), 1 H), 1.22 (d, 6H). To a solution of 2-METHYL-2- (3-PIPERIDIN-3-YL-PHENOXY)-PROPIONIC acid benzyl ester (Preparation 2, Method C; 30 mg, 0.085 mmol) in 1 mL methylene chloride was added 4-isopropylphenoxyacetic acid (33mg, 0.17 mmol) and 1- (3- DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE HYDROCHLORIDE (33mg, 0.17 mmol) and allowed to stir 18 h at ambient temperature. The reaction was concentrated under reduced pressure and the resultant oil flash chromatographed with 30percent ethyl acetate/hexanes to yield 35mg (78percent) OF 2- (3- {1- [ (4-ISOPROPYL-PHENOXY)-ACETYL]- PIPERIDIN-3-YL}-PHENOXY)-2-METHYL-PROPIONIC acid benzyl ester as a clear oil. LC-MS 530.6 (M + H) +. 'H NMR (400 MHz, CDCI3) S 7.24 (m, 5H), 7.14 (m, 3H), 6.89 (m, 2H), 6.83 (m, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 5.19 (s, 2H), 4.64 (m, 3H), 4.07 (d, 1H), 3.04 (t, 1 H), 2.97 (m, 1 H), 2.89 (m, 1 H), 2.47 (m, 2H), 1.95 (m, 1 H), 1.82 (m, 1 H), 1.61, (s, 6H), 1.21 (d, 6H). 10percent Palladium on carbon (4 mg, 10 wtpercent) was added to a solution of 2- (3- {1- [ (4-ISOPROPYL-PHENOXY)-ACETYL]-PIPERIDIN-3-YLL-PHENOXY)-2-METHYL-PROPIONIC ACID BENZYI ester (35 mg, 0.066 mmol) in methanol (2 mL) and the resulting mixture hydrogenated at atmospheric pressure for 3 h. The reaction mixture was filtered through a plug of celite and the celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure to provide 29 mg (99percent) of 2-(3-{1-[(4-Isopropyl-phenoxy)-acetyl]-piperidin-3-yl]-phenoxy)-2-methyl- propionic acid as a clear oil. LC-MS 440.5 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.19 (t, 1H), 7.14 (t, 2H), 6.87 (m, 3H), 6.81 (m, 2H), 4.66 (m, 3H), 4.04 (dd, 1 H), 3.05 (m, 1H), 2.85 (m, 1 H), 2.65 (m, 2H), 2.02 (t, 1H), 1.82 (t, 1H), 1.65 (m, 1H), 1.59, (s, 6H), 1.21 (d, 6H).

Reference： [1] Patent: WO2004/48334, 2004, A1, . Location in patent: Page 128-130

2
[ 184878-99-7 ]
[ 1643-16-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 24, p. 4783 - 4803
[2] Patent: WO2007/120012, 2007, A1, . Location in patent: Page/Page column 88-89

3
[ 1401223-60-6 ]
[ 1643-16-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3154 - 3156

4
[ 99-89-8 ]
[ 305-53-3 ]
[ 1643-16-9 ]

Reference： [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2017, vol. 32, # 1, p. 513 - 521

5
[ 99-89-8 ]
[ 1643-16-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3154 - 3156
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805

6
[ 99-89-8 ]
[ 79-11-8 ]
[ 1643-16-9 ]

Reference： [1] Gazzetta Chimica Italiana, 1880, vol. 10, p. 248[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1880, p. 663

[ 1643-16-9 ] Synthesis Path-Downstream 1~69

1
[ 99-89-8 ]
[ 79-11-8 ]
[ 1643-16-9 ]

Reference： [1]Gazzetta Chimica Italiana,1880,vol. 10,p. 248
Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1880,p. 663

2
[ 1643-16-9 ]
[ 94410-57-8 ]
5-(Dichloro-methanesulfonyl)-2-(4-isopropyl-phenoxymethyl)-1H-benzoimidazole [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1983,vol. 57,p. 1037 - 1043

3
[ 1643-16-9 ]
[ 530-62-1 ]
[ 173978-79-5 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 9277 - 9280

4
[ 1643-16-9 ]
[ 124-68-5 ]
[ 184879-00-3 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

5
[ 1643-16-9 ]
[ 620-20-2 ]
3-(3-Chloro-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

6
[ 184878-99-7 ]
[ 1643-16-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 22: N-(3-Fluoro-4-methanesuIfonylaminobenzyl)-2-(4- isopropylphenoxy)acetamideStep 1 : Synthesis of 4-isopropylphenoxyacetic acid; To a solution of 4-isopropylphenol (0.38 g, 2.79 mmol) in acetonitrile (10 mL) were added cesium carbonate (1.37 g, 4.2 mmol) and ethyl bromoacetate (0.34 mL, 3.01 mmol). The resulting mixture was stirred for 1.5 hours at room temperature, concentrated under reduced pressure, and diluted with EtOAc and water. The organic layer was washed with brine and concentrated under reduced pressure. The crude residue was diluted with THF (7 mL) and 1 N LiOH (5 mL), and then stirred for 1 hour at room temperature. The mixture was acidified with 6 N HCI, concentrated under reduced pressure, and diluted with EtOAc and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was then purified by recrystallization from EtOAc/hexane to afford 0.35 g (64.6%) as a white solid. 1H NMR (300 MHz, CDCI3): delta 7.17 (d, 2 H, J = 8.7 Hz), 6.86 (d, 2 H, J = 8.7 Hz), <n="90"/>4.66 (s, 2 H), 2.87 (sept, 1 H1 J = 7.2 Hz), 1.22 (d, Q H1 J = 7.2 Hz)

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803
[2]Patent: WO2007/120012,2007,A1 .Location in patent: Page/Page column 88-89

Yield	Reaction Conditions	Operation in experiment
		The high activity of these compounds, especially on bindweed, was by no means foreseeable and was all the more surprising insofar as related compounds such as 3,4-dimethylphenoxy acetic acid 4-isopropylphenoxy acetic acid 4-ethylphenoxy acetic acid 2-chloro-4-isopropylphenoxy acetic acid

8
[ 1643-16-9 ]
4-CH₃C₆H₄CH₂X X=Br or Cl [ No CAS ]
2-(4-Isopropyl-phenoxy)-3-p-tolyl-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

9
[ 1643-16-9 ]
4-ClC₆H₄CH₂X X=Br or Cl [ No CAS ]
3-(4-Chloro-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

10
[ 1643-16-9 ]
4-BrC₆H₄CH₂X X=Br or Cl [ No CAS ]
3-(4-Bromo-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

11
[ 1643-16-9 ]
4-CH₃OC₆H₄CH₂X X=Br or Cl [ No CAS ]
2-(4-Isopropyl-phenoxy)-3-(4-methoxy-phenyl)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

12
[ 1643-16-9 ]
2,4-Cl₂C₆H₃CH₂X X=Br or Cl [ No CAS ]
3-(2,4-Dichloro-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

13
[ 1643-16-9 ]
β-naphthyl-CH2X X=Br or Cl [ No CAS ]
2-(4-Isopropyl-phenoxy)-3-naphthalen-2-yl-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

14
[ 1643-16-9 ]
3,4-Cl₂C₆H₃CH₂X X=Br or Cl [ No CAS ]
3-(3,4-Dichloro-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

15
[ 1643-16-9 ]
[ 713517-90-9 ]
5-(2,6-dichloro-benzyl)-1-(4-isopropyl-phenoxy)-9b-phenyl-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2776 - 2795

16
[ 1643-16-9 ]
[ 478165-02-5 ]
N-{4-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-ylmethyl]-5-nitro-6-oxo-1,6-dihydro-pyrimidin-2-yl}-2-(4-isopropyl-phenoxy)-acetamide [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2002,vol. 15,p. 1460 - 1465

17
[ 1643-16-9 ]
[ 833480-26-5 ]
[ 833480-27-6 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 141 - 149

18
[ 1643-16-9 ]
[ 223128-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; for 2h;	To a Stem'reaction tube containing (4-isopropylphenoxy) acetic acid (58.3 mg, 0.3 MMOL) in THF (0.5 mL) was added oxalyl chloride (25 muL, 0.3 MMOL) and a drop of DMF. The reaction mixture was flushed with nitrogen, capped and shaken for 2 hours. SOLID N- (3-AMINO-2-ETHYL- imidazo [1, 2-a] PYRAZIN-6-YL)-2, 2, 2-trifluoroacetamide (55 mg, 0.2 MMOL) and a solution of diisopropylethylamine (70 pL, 0.4 MMOL) in THF (0.5 mL) was added to the acid chloride solution and the reaction again flushed with nitrogen and capped. After heating to 60 OC for 16 hours, the tubes were uncapped and a solution of sodium hydroxide (40 mg, 1 MMOL) in H20 (0. 5 mL) added to the reaction mixture which was heated for a further 4 hours. The tubes were allowed cool and the contents diluted with DMSO (0.5 mL), filtered and purified by reverse-phase preparative HPLC to yield the desired amide (30) as a pale yellow solid (30.4 mg, 43%). HPLC 100% ; MS (ES) 356 [M+H] +.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 C. The solution was stirred for another 2 hrs at 25 C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3783 - 3805
[2]Organic Letters,2002,vol. 4,p. 4205 - 4208
[3]Patent: WO2004/85409,2004,A2 .Location in patent: Page 87-88
[4]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6666 - 6672
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3931 - 3938

19
[ 1643-16-9 ]
4-ClC₆H₄CH₂X X=Br or Cl [ No CAS ]
rac-(SR)-[(5SR)-1-(2,6-dichlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-(4-isopropylphenoxy)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2776 - 2795

20
[ 1643-16-9 ]
[ 479408-38-3 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 4205 - 4208

21
[ 1643-16-9 ]
[ 479408-42-9 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 4205 - 4208

22
[ 1643-16-9 ]
[ 479408-36-1 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 4205 - 4208

23
[ 99-89-8 ]
platinum [ No CAS ]
[ 1643-16-9 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

24
[ 1643-16-9 ]
[ 1026600-60-1 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

25
[ 1643-16-9 ]
2-(4-Isopropyl-phenoxy)-3-(4-trifluoromethyl-phenyl)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

26
[ 1643-16-9 ]
2-[1-(4-Isopropyl-phenoxy)-2-(4-trifluoromethyl-phenyl)-ethyl]-4,4-dimethyl-4,5-dihydro-oxazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

27
[ 1643-16-9 ]
[ 184879-01-4 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

28
[ 1643-16-9 ]
3-(3-Fluoro-phenyl)-2-(4-isopropyl-phenoxy)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

29
[ 1643-16-9 ]
2-(4-Isopropyl-phenoxy)-3-(2-trifluoromethyl-phenyl)-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4783 - 4803

30
[ 1643-16-9 ]
N-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-2-(4-isopropyl-phenoxy)-acetamide [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 9277 - 9280

31
[ 1643-16-9 ]
N-[9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-2-(4-isopropyl-phenoxy)-acetamide [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 9277 - 9280

32
[ 1643-16-9 ]
N-[9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-9H-purin-6-yl]-2-(4-isopropyl-phenoxy)-acetamide [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 9277 - 9280

33
[ 1643-16-9 ]
[ 7689-03-4 ]
[ 401478-54-4 ]

Yield	Reaction Conditions	Operation in experiment
80.0%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 20h;	The mixture of camptothecin (10 mg, 0.029 mmol), <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> (8 mg, 0.42 mmol), EDCI (28 mg, 0.15 mmol), DMAP (2 mg, 0.02 mmol) and dichloromethane (3 ml) was stirred in the room temperature for 20 h, then dichloromethane (20 ml) was added to the solution. Organic layer was washed with water (20 ml), saturated NaHCO3 aqueous solution (10 ml) and brine (20 ml), and then dried over MgSO4. After the solvent was removed under reduced pressure, the resulting solid was separated by column chromatography (eluent: CHCl3:CH3OH 9:1) to afford 12 mg camptothecin-20-O-4-isopropylphenoxyacetate, yield: 80.0%, mp 208-210 C. The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz): delta 8.42 (s, 1H, Ar-H), 8.23 (d, 1H, Ar-H), 7.98 (d, 1H, Ar-H), 7.85 (t, 1H, Ar-H), 7.69 (t, 1H, Ar-H), 7.10 (s, 2H, Ar-H), 6.84 (d, 2H, Ar-H), 5.63 (d, 1H, H17), 5.63 (d, 1H, H17), 5.25 (q, 2H, H5), 4.84 (q, 2H, OCH2CO), 2.72 (m, 1H, CHMe2), 2.21 (dm, 2H, CH2), 1.00 (m, 9H, CH3).

Reference： [1]Patent: US6350756,2002,B1 .Location in patent: Page column 36

34
[ 702679-58-1 ]
[ 1643-16-9 ]
2-(3-{1-[(4-isopropylphenoxy)acetyl]piperidin-3-yl}phenoxy)-2-methylpropionic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	To a solution of 4-isopropylphenol (1. 007g, 7.39 mmol) in 15 mL DIMETHYLFORMAMIDE was added potassium carbonate (2.04g, 14.79 mmol) and ethyl bromoacetate (1.23 mL, 11.09 MMOL). The reaction was stirred for 48 h at ambient temperature. The mixture was diluted with 500 mL water and extracted with diethyl ether (2 x 200 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 10% ethyl acetate/hexanes to yield 1. 61G (98%) of ETHYL- (4-ISOPROPYLPHENOXY) acetate as a clear oil. MS (APCI) 223.3 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.14 (d, 2H), 6.84 (d, 2H), 4.59 (s, 2H), 4.27 (q, 2H), 2.86 (m, 1H), 1.30 (t, 3H), 1.21 (d, 6H). A mixture of ETHYL- (4-ISOPROPYLPHENOXY) acetate (1.61g, 7.24 mmol) and 2N NaOH (aq) (10.9 mL) in 20 mL of methanol was stirred at ambient temperature for 3 h and concentrated under reduced pressure. The resulting residue was taken up in water (100 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2 x 100 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 1. 32G (94%) of <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> as a white solid. MS (APCI) 195.3 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.17 (d, 2H), 6.86 (d, 2H), 4.66 (s, 2H), 2.87 (m), 1 H), 1.22 (d, 6H). To a solution of 2-METHYL-2- (3-PIPERIDIN-3-YL-PHENOXY)-PROPIONIC acid benzyl ester (Preparation 2, Method C; 30 mg, 0.085 mmol) in 1 mL methylene chloride was added <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> (33mg, 0.17 mmol) and 1- (3- DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE HYDROCHLORIDE (33mg, 0.17 mmol) and allowed to stir 18 h at ambient temperature. The reaction was concentrated under reduced pressure and the resultant oil flash chromatographed with 30% ethyl acetate/hexanes to yield 35mg (78%) OF 2- (3- {1- [ (4-ISOPROPYL-PHENOXY)-ACETYL]- PIPERIDIN-3-YL}-PHENOXY)-2-METHYL-PROPIONIC acid benzyl ester as a clear oil. LC-MS 530.6 (M + H) +. 'H NMR (400 MHz, CDCI3) S 7.24 (m, 5H), 7.14 (m, 3H), 6.89 (m, 2H), 6.83 (m, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 5.19 (s, 2H), 4.64 (m, 3H), 4.07 (d, 1H), 3.04 (t, 1 H), 2.97 (m, 1 H), 2.89 (m, 1 H), 2.47 (m, 2H), 1.95 (m, 1 H), 1.82 (m, 1 H), 1.61, (s, 6H), 1.21 (d, 6H). 10% Palladium on carbon (4 mg, 10 wt%) was added to a solution of 2- (3- {1- [ (4-ISOPROPYL-PHENOXY)-ACETYL]-PIPERIDIN-3-YLL-PHENOXY)-2-METHYL-PROPIONIC ACID BENZYI ester (35 mg, 0.066 mmol) in methanol (2 mL) and the resulting mixture hydrogenated at atmospheric pressure for 3 h. The reaction mixture was filtered through a plug of celite and the celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure to provide 29 mg (99%) of 2-(3-{1-[(4-Isopropyl-phenoxy)-acetyl]-piperidin-3-yl]-phenoxy)-2-methyl- propionic acid as a clear oil. LC-MS 440.5 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.19 (t, 1H), 7.14 (t, 2H), 6.87 (m, 3H), 6.81 (m, 2H), 4.66 (m, 3H), 4.04 (dd, 1 H), 3.05 (m, 1H), 2.85 (m, 1 H), 2.65 (m, 2H), 2.02 (t, 1H), 1.82 (t, 1H), 1.65 (m, 1H), 1.59, (s, 6H), 1.21 (d, 6H).

Reference： [1]Patent: WO2004/48334,2004,A1 .Location in patent: Page 128-130

35
[ 14062-21-6 ]
[ 1643-16-9 ]

Yield	Reaction Conditions	Operation in experiment
94%		To a solution of 4-isopropylphenol (1. 007g, 7.39 mmol) in 15 mL DIMETHYLFORMAMIDE was added potassium carbonate (2.04g, 14.79 mmol) and ethyl bromoacetate (1.23 mL, 11.09 MMOL). The reaction was stirred for 48 h at ambient temperature. The mixture was diluted with 500 mL water and extracted with diethyl ether (2 x 200 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 10% ethyl acetate/hexanes to yield 1. 61G (98%) of ETHYL- (4-ISOPROPYLPHENOXY) acetate as a clear oil. MS (APCI) 223.3 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.14 (d, 2H), 6.84 (d, 2H), 4.59 (s, 2H), 4.27 (q, 2H), 2.86 (m, 1H), 1.30 (t, 3H), 1.21 (d, 6H). A mixture of ETHYL- (4-ISOPROPYLPHENOXY) acetate (1.61g, 7.24 mmol) and 2N NaOH (aq) (10.9 mL) in 20 mL of methanol was stirred at ambient temperature for 3 h and concentrated under reduced pressure. The resulting residue was taken up in water (100 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2 x 100 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 1. 32G (94%) of 4-isopropylphenoxyacetic acid as a white solid. MS (APCI) 195.3 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.17 (d, 2H), 6.86 (d, 2H), 4.66 (s, 2H), 2.87 (m), 1 H), 1.22 (d, 6H). To a solution of 2-METHYL-2- (3-PIPERIDIN-3-YL-PHENOXY)-PROPIONIC acid benzyl ester (Preparation 2, Method C; 30 mg, 0.085 mmol) in 1 mL methylene chloride was added 4-isopropylphenoxyacetic acid (33mg, 0.17 mmol) and 1- (3- DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE HYDROCHLORIDE (33mg, 0.17 mmol) and allowed to stir 18 h at ambient temperature. The reaction was concentrated under reduced pressure and the resultant oil flash chromatographed with 30% ethyl acetate/hexanes to yield 35mg (78%) OF 2- (3- {1- [ (4-ISOPROPYL-PHENOXY)-ACETYL]- PIPERIDIN-3-YL}-PHENOXY)-2-METHYL-PROPIONIC acid benzyl ester as a clear oil. LC-MS 530.6 (M + H) +. 'H NMR (400 MHz, CDCI3) S 7.24 (m, 5H), 7.14 (m, 3H), 6.89 (m, 2H), 6.83 (m, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 5.19 (s, 2H), 4.64 (m, 3H), 4.07 (d, 1H), 3.04 (t, 1 H), 2.97 (m, 1 H), 2.89 (m, 1 H), 2.47 (m, 2H), 1.95 (m, 1 H), 1.82 (m, 1 H), 1.61, (s, 6H), 1.21 (d, 6H). 10% Palladium on carbon (4 mg, 10 wt%) was added to a solution of 2- (3- {1- [ (4-ISOPROPYL-PHENOXY)-ACETYL]-PIPERIDIN-3-YLL-PHENOXY)-2-METHYL-PROPIONIC ACID BENZYI ester (35 mg, 0.066 mmol) in methanol (2 mL) and the resulting mixture hydrogenated at atmospheric pressure for 3 h. The reaction mixture was filtered through a plug of celite and the celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure to provide 29 mg (99%) of 2-(3-{1-[(4-Isopropyl-phenoxy)-acetyl]-piperidin-3-yl]-phenoxy)-2-methyl- propionic acid as a clear oil. LC-MS 440.5 (M + H) +. 'H NMR (400 MHz, CDCI3) 8 7.19 (t, 1H), 7.14 (t, 2H), 6.87 (m, 3H), 6.81 (m, 2H), 4.66 (m, 3H), 4.04 (dd, 1 H), 3.05 (m, 1H), 2.85 (m, 1 H), 2.65 (m, 2H), 2.02 (t, 1H), 1.82 (t, 1H), 1.65 (m, 1H), 1.59, (s, 6H), 1.21 (d, 6H).

Reference： [1]Patent: WO2004/48334,2004,A1 .Location in patent: Page 128-130

36
[ 1643-16-9 ]
N-[2-(3-chlorophenyl)ethyl]-2-([(([4-(1-methylethyl)phenyl]oxy)acetyl)amino]methyl)-1,3-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		Example 55; [0266] 2-[2-(4-Isopropyl-phenoxy)-acetylamino]-methyl)-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide: 2-Aminomethyl-thiazole-4-carboxylic acid [2-(3- chloro-phenyl)-ethyl]-amide (50 mg, 0.17 mmol) was dissolved in DMF (1 mL). EDC (38 mg, 0.2 mmol) and HOBt (27 mg, 0.2 mmol) where added and the mixture was stirred at ambient temperature for 10 minutes. (4-Isopropyl-phenoxy)-acetic acid (33 mg, 0.17 mmol) was added. The reaction mixture was stirred at ambient temperature for 18 hours. DI water was added and the mixture was extracted with ethyl acetate x3. The combined organic layers were washed with 1 N hydrochloric acid x2,2 N sodium hydroxide x2,1 N sodium bicarbonate x2, DI water x2 and brine xl, dried over sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography using silica (1:1 Ethyl acetate: Hexanes) to give the title compound as a semi-solid (16.8mg, 21%). 'H NMR (400 MHz, d6-DMSO): 9.02 (t, 1H), 8.41 (t, 1H), 8.11 (s, 1H), 7.27 (m, 3H), 7.16 (m, 3H), 6.88 (d, 2H), 4.61 (d, 2H), 4.56 (s, 2H), 3.48 (q, 2H), 2.83 (m, 3H), 1.17 (d, 6H) ; MS (ESI-LCMS) for C24H27ClN303S: 472 (MH+).

Reference： [1]Patent: WO2005/97765,2005,A1 .Location in patent: Page/Page column 292

37
[ 79-37-8 ]
[ 1643-16-9 ]
[ 90719-32-7 ]
[ 223127-28-4 ]
[ 223128-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;	(a) (S)-4-benzyl-3-[(4-isopropylphenoxy)acetyl]oxazolidine-2-one Oxalyl chloride (16.8 ml) and N,N-dimethylformamide (three drops) were added to a solution of <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> (15.0 g) in dichloromethane (75 ml) at ambient temperature. The reaction mixture was stirred for 1.5 hours. The reaction mixture was concentrated at reduced pressure and residual reagents were azeotropically evaporated off with toluene. The residue was dried under reduced pressure. A solution of n-butyl lithium in hexane (1.61N, 48.0 ml) was added dropwise to a solution of (S)-4-benzyloxazolidine-2-one (12.4 g) in tetrahydrofuran (150 ml) at -78 C. and the mixture was stirred at the same temperature for 30 minutes. To this solution a solution of 4-isopropylphenoxyacetyl chloride, which had been obtained above, in tetrahydrofuran (100 ml) was added at -78 C. The mixture was stirred at 0 C. for 1 hour. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with aqueous hydrogen chloride solution (1N), saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a mixture of hexane/ethyl acetate=6/1 to afford the desired compound (20.9 g) as colorless crystals. mp 104.5-105 C. 1H-NMR (270 MHz, CDCl3): delta ppm 1.23 (6H, d, J=7.0 Hz), 2.79-2.92 (2H, m), 3.36 (1H, dd, J=3.0, 13.5 Hz), 4.24-4.37 (2H, m), 4.68-4.78 (1H, m), 5.22 (2H, s), 6.91 (2H, d, J=8.5 Hz), 7.13-7.38 (7H, m).

Reference： [1]Patent: US6528525,2003,B1

38
[ 79-37-8 ]
[ 1643-16-9 ]
[ 40217-17-2 ]
[ 223127-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In hexane;	(a) (R)-4-benzyl-3-[(4-isopropylphenoxy)acetyl]oxazolidine-2-one In a similar manner to that described in Refernce example 29(a), a reaction was carried out using <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> (14.1 g), oxalyl chloride (15.8 ml), (R)-4-benzyloxazolidine-2-one (11.7 g) and a solution of n-butyl lithium in hexane (1.61N, 45.0 ml) and the reaction mixture was treated to afford the desired compound (18.6 g) as colorless crystals. mp 104.5-105.5C. 1H-NMR (400 MHz, CDCl3): delta ppm 1.23 (6H, d, J=7.0 Hz), 2.80-2.91 (2H, m), 3.36 (1H, dd, J=3.0, 13.5 Hz), 4.28 (1H, dd, J=3.0, 9.0 Hz), 4.33 (1H, dd, J=8.0, 9.0 Hz), 4.68-4.78 (1H, m), 5.22 (2H, s), 6.91 (2H, d, J=8.5 Hz), 7.14-7.38 (7H, m).

Reference： [1]Patent: US6528525,2003,B1

39
[ 13382-43-9 ]
[ 1643-16-9 ]
2-(4-isopropylphenoxy)-N-(2-methylbenzo[d]thiazol-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris(dimethylamino)chlorophosphonium perchlorate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20℃;	A mixture of <strong>[1643-16-9]4-isopropylphenoxyacetic acid</strong> (6 rag, 0.03 mmol), N,N- diisopropylethylamine (21 muL, 0.12 mmol) and tris(dimethylamino)chlorophosphonium perchlorate (31 mg, 0.09 mmol) was dissolved in N-methylpyrrolidone (200 muL) followed by the addition of the solution of 2-methyl-benzothiazol-6-ylamine (5 mg, 0.03 mmol) in N- methylpyrrolidone (150 muL). The reaction mixture was maintained at room temperature overnight. The resulting solution was subjected to HPLC purification (Phenomenex Synergi 4 mum Max-RP column (10 mm x 50 mm); flow rate = 6 mL/min; injection volume = 200 muL; mobile phase A: 100% water containing 0.1 % trifluoroacetic acid (TFA); mobile phase B: 100% acetonitrile containing 0.1% trifluoroacetic acid (TFA); gradient elution from 10% B to 100% B over 8 min) to provide the title compound (5.8 mg) as a colorless film. LC/MS (ESI) m/z 341.1 [M+H]. HPLC retention time (Method A) = 3.47 min.

Reference： [1]Patent: WO2007/67757,2007,A2 .Location in patent: Page/Page column 42

40
[ 1144523-78-3 ]
[ 1643-16-9 ]
[ 1144523-79-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	Intermediate 49; <n="52"/>Methyl 3-{2-r({f4-(1 -methylethyl)phenv?oxy)acetyl)amino1ethyl)-1 -phenyl-1 H-indole- 5-carboxylate; To a solution of methyl 3-(2-aminoethyl)-1 -phenyl-1 H-indole-5-carboxylate hydrochloride (Intermediate 48) (200 mg, 0.6 mmol) in 20 ml of DMF was added, HOBT (107 mg, 0.79 mmol), EDCI (152 mg, 0.79 mmol), [4-(1-methylethyl)phenyl]oxy}acetic acid (153.4 mg, 0.79 mmol), and triethylamine (335 mul, 2.42 mmol), then the reaction mixture was stirred 16H at room temperature. Water (200 ml) and ethyl acetate (30 ml) were added. The aqueous phase was extracted with ethyl acetate and the organic phase was dried over Na2SO4, filtered and concentrated to give the title compound (305 mg, quantitative yield). LC/MS : m/z 471 (M+H)+, Rt: 4.09

Reference： [1]Patent: WO2009/47240,2009,A1 .Location in patent: Page/Page column 50-51

41
[ 1643-16-9 ]
[ 51468-14-5 ]
[ 1221899-01-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2224 - 2228

42
[ 1643-16-9 ]
(3-fluoro-4-(methylsulfonamido)phenyl)methanaminium chloride [ No CAS ]
N-(3-fluoro-4-methanesulfonylaminobenzyl)-2-(4-isopropylphenoxy)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.0%		Step 2: Synthesis of N-(3-fluoro-4-methanesulfonylaminobenzyl)-2-(4- isopropylphenoxy)acetamide; To a suspension of 3-fluoro-4-methanesulfonylaminobenzylamine hydrochloride (100 mg, 0.39 mmol) in THF (5 mi_) was added triethyiamine (82 mul_, 0.59 mmol). The mixture was stirred for 5 min, to which were added 4- isopropylphenoxyacetic acid (81 mg, 0.42 mmol) and 4-(4,6- dimethoxy[1 ,3,5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMTMM1 120 mg, 0.43 mmol). The mixture was stirred overnight at room temperature and was concentrated under reduced pressure. The residue was diluted with EtOAc and water. The organic layer was washed with 3N HCI, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by recrystallization from EtOAc/hexane to afford 110 mg (71.0%) as a white solid.Melting point: 118 - 119.50C;1H NMR (300 MHz, CDCI3): delta 7.52 (t, 1 H, J = 8.1 Hz), 7.18 (d, 2 H, J = 8.4 Hz), 7.10 ~ 7.05 (m, 2 H), 6.97 (br, 1 H), 6.85 (d, 2 H, J = 8.7 Hz), 6.48 (br s, 1 H), 4.55 (s, 2 H), 4.52 (d, 2 H, J = 6 Hz), 3.02 (s, 3 H), 2.88 (sept, 1 H1 J = 7.2 Hz), 1.23 (d, 6 H, J = 7.2 Hz)

Reference： [1]Patent: WO2007/120012,2007,A1 .Location in patent: Page/Page column 89

43
[ 4928-46-5 ]
[ 1643-16-9 ]
[ 1435933-37-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3154 - 3156

44
[ 99-89-8 ]
[ 1643-16-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3154 - 3156
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 3783 - 3805

45
[ 1401223-60-6 ]
[ 1643-16-9 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3783 - 3805
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3154 - 3156

46
[ 1643-16-9 ]
[ 1401223-27-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3783 - 3805

47
[ 1643-16-9 ]
[ 186668-40-6 ]
[ 631090-46-5 ]

Yield	Reaction Conditions	Operation in experiment
84.1%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	General procedure: Taking compound 6 for example, a mixture of hCPT (15mg, 0.041mmol); 2,3,4,5,6-pentafluorophenoxyacetic acid (30 mg, 0.124mmol); EDCI (30mg, 0.157mmol); 4-DMAP(12mg, 0.098mmol); and dichloromethane(5 ml) was stirred at room temperature for 8-12 h. The reaction was monitored by thin layer chromatographyuntil the end. Then, chloroform (40 ml) was added, and organic phase was washed with water (35ml), saturated sodium bicarbonate aqueous solution (35 ml) and brine (35 ml),and then dried over magnesium sulfate. After the solvent was removed under reduced pressure, the residue was taken upin chloroform and chromatographed (eluent:CHCl3-CH3OH 98:2) on silica gel to give 14 mg of compound 6 as a pale yellowsolid.

Reference： [1]Journal of Asian Natural Products Research,2013,vol. 15,p. 1179 - 1188

48
[ 517-89-5 ]
[ 1643-16-9 ]
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 2-(4-isopropylphenoxy)acetate [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 35588 - 35596

49
[ 1643-16-9 ]
C₂₀H₂₂FNO₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6666 - 6672

50
[ 1643-16-9 ]
2-(2-fluoro-4-(2-(4-isopropylphenoxy)acetamido)phenoxy)acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6666 - 6672

51
[ 1643-16-9 ]
[ 41220-34-2 ]
C₂₄H₃₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	Preparation Example 1 Synthesis of Compound 1 (0191) (0192) A vial was charged with a carboxylic acid (330 mg, 1.1 equiv.), a solvent (1 mL of a solution of 200 g N-oxybenzotriazole in 1 L of DMF), and an amine (316 mg, 1 equiv.). To the stirred reaction mixture, EDC was added (290 mg, 1.21 equiv.). Incase the reaction mixture became highly viscous, some more DMF was added. In case the reaction mixture was a homogeneous solution, it was kept at room temperature for 72 hrs. Otherwise the reaction mixture was sonicated at room temperature for 5 days. The reaction mixture was diluted with 1% aqueous sodium phosphate solution until the vial was full. Then the vial was sonicated. In case a crystalline precipitate was formed, the vial was subjected to the filtration. In case an oily product was formed, the product was dissolved in methanol and precipitated by an addition of 4% hydrochloric acid. Alternatively 2-propanol (1 mL) was mixed with the crude product and the mixture was sonicated. Then the solution was diluted with 5% aqueous sodium hydrogen carbonate solution (the procedure repeated 2-3 times if necessary). The crude product was purified by chromatography (silica gel, chloroform:2-propanol=4:1). The yield was 425 mg (72%).

Reference： [1]Patent: US2016/214967,2016,A1 .Location in patent: Paragraph 0191; 0192

52
[ 1643-16-9 ]
[ 68304-97-2 ]
C₂₄H₃₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	Preparation Example 2 Synthesis of Compound 2 (0193) (0194) A vial was charged with a carboxylic acid (339 mg, 1.1 equiv.), a solvent (1 mL of a solution of 200 g N-oxybenzotriazole in 1 L of DMF), and an amine (324 mg, 1 equiv.). To the stirred reaction mixture, EDC was added (298 mg, 1.21 equiv.). Incase the reaction mixture became highly viscous, some more DMF was added. In case the reaction mixture was a homogeneous solution, it was kept at room temperature for 72 hrs. Otherwise the reaction mixture was sonicated at room temperature for 5 days. The reaction mixture was diluted with 1% aqueous sodium phosphate solution until the vial was full. Then the vial was sonicated. Incase a crystalline precipitate was formed, the vial was subjected to the filtration. In case an oily product was formed, the product was dissolved in methanol and precipitated by an addition of 4% hydrochloric acid. Alternatively 2-propanol (1 mL) was mixed with the crude product and the mixture was sonicated. Then the solution was diluted with 5% aqueous sodium hydrogen carbonate solution (the procedure repeated 2-3 times if necessary). The crude product was purified by chromatography (silica gel, chloroform:2-propanol=4:1). The yield was 590 mg (98%).

Reference： [1]Patent: US2016/214967,2016,A1 .Location in patent: Paragraph 0193; 0194

53
[ 58255-25-7 ]
[ 1643-16-9 ]
C₁₈H₂₃NO₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3931 - 3938

54
[ 1643-16-9 ]
C₁₈H₂₃NO₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3931 - 3938

55
[ 52333-90-1 ]
[ 1643-16-9 ]
2-(4-isopropylphenoxy)-N-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)acetamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2017,vol. 32,p. 513 - 521

56
[ 99-89-8 ]
[ 305-53-3 ]
[ 1643-16-9 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2017,vol. 32,p. 513 - 521

57
[ 1108137-69-4 ]
[ 1643-16-9 ]
1-(4-isopropylphenoxyacetyl)lycorine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.8%		10-a: Place 2-TBS-lycoline (1.0 mmol), 4-isopropyl-phenoxyacetic acid (1.2 mmol), EDCI (1.2 mmol), DMAP (0.12 mmol), 15 ml of dichloromethane, place in In a 50ml reaction flask, stir at room temperature until no raw materials remain. Transfer to a separatory funnel, add 50 ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and concentrate for later use.10-b: Put the above product, TBAF (2.0 mmol), 15 ml of THF, into a 50 ml reaction flask, and stir at room temperature until no raw materials remain. Transfer to a separatory funnel, add 50 ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography to obtain a white solid (59.8% ).

Reference： [1]Patent: CN110759927,2020,A .Location in patent: Paragraph 0146-0149

58
[ 184878-97-5 ]
[ 1643-16-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide In methanol; water at 20℃; for 1.5h;

Reference： [1]Suigo, Lorenzo; Chojnacki, Michaelle; Zanotto, Carlo; Sebastián-Pérez, Victor; Morghen, Carlo De Giuli; Casiraghi, Andrea; Dunman, Paul M.; Valoti, Ermanno; Straniero, Valentina [Antibiotics, 2021, vol. 10, # 4]

59
[ 1643-16-9 ]
3,5-dichloro-N-((2-(4-isopropylphenoxy)acetamido)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: hydrogenchloride / methanol; water / 0.5 h / Reflux 4: triethylamine / dichloromethane / 20 °C

60
[ 1643-16-9 ]
3,5-dichloro-N-((2-(4-i-propylphenoxy)acetamido)ethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 1 h / 20 °C

61
[ 1643-16-9 ]
4-(3,5-dichlorobenzoylamino)-1-(4-isopropylphenoxyacetyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 4: triethylamine / dichloromethane / 3 h / 0 - 20 °C

62
[ 1643-16-9 ]
4-(3,5-dichlorobenzoyl)-1-(4-i-propylphenoxyacetyl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 4: triethylamine / dichloromethane / 3 h / 0 - 20 °C

63
[ 1643-16-9 ]
N-(t-butoxycarbonylaminomethyl)-4-i-propylphenoxyacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C

64
[ 1643-16-9 ]
N-(aminomethyl)-2-(4-i-propylphenoxy)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: hydrogenchloride / methanol; water / 0.5 h / Reflux

65
[ 1643-16-9 ]
4-t-butoxycarbonylamino-1-(4-i-propylphenoxyacetyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C

66
[ 1643-16-9 ]
4-t-butoxycarbonyl-1-(4-i-propylphenoxyacetyl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C

67
[ 1643-16-9 ]
4-amino-1-(4-isopropylphenoxyacetyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C

68
[ 1643-16-9 ]
1-(4-isopropylphenoxyacetyl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C

69
[ 1108137-69-4 ]
[ 1643-16-9 ]
C₃₃H₄₃NO₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	10.10-a 10-a: 2-TBS-lycorine (1.0 mmol), 4-isopropyl-phenoxyacetic acid (1.2 mmol), EDCI (1.2 mmol), DMAP (0.12 mmol), and dichloromethane (15 ml) were fed to a 50 ml reaction flask, and stirred at room temperature until no raw materials remained. The reaction solution was transferred to a separatory funnel, and dichloromethane (50 ml) was added. The organic phase was washed respectively with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated for use.

Reference： [1]Current Patent Assignee: BEIJING DYNE HIGH TECH PEDIATRIC PHARMACEUTICAL R AND D INSTITUTE; SHANDONG DYNE MARINE BIOPHARMACEUTICAL - US2021/206777, 2021, A1 Location in patent: Paragraph 0066-0067

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 1643-16-9 ] {[proInfo.proName]}

Quality Control of [ 1643-16-9 ]

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Product Details of [ 1643-16-9 ]

Calculated chemistry of [ 1643-16-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1643-16-9 ]

Application In Synthesis of [ 1643-16-9 ]

[ 1643-16-9 ] Synthesis Path-Upstream 1~6

[ 1643-16-9 ] Synthesis Path-Downstream 1~69

Related Functional Groups of [ 1643-16-9 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1643-16-9 ]