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Quality Control of [ 28920-43-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 28920-43-6 ]

SDS Specification

Alternatived Products of [ 28920-43-6 ]

Product Details of [ 28920-43-6 ]

CAS No. :	28920-43-6	MDL No. :	MFCD00001138
Formula :	C₁₅H₁₁ClO₂	Boiling Point :	-
Linear Structure Formula :	C₁₃H₉CH₂OC(O)Cl	InChI Key :	IRXSLJNXXZKURP-UHFFFAOYSA-N
M.W :	258.70	Pubchem ID :	34367
Synonyms :

Calculated chemistry of [ 28920-43-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.13
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.97
TPSA :	26.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.74
Log Po/w (XLOGP3) :	4.52
Log Po/w (WLOGP) :	4.17
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	3.92
Consensus Log Po/w :	3.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.59
Solubility :	0.0067 mg/ml ; 0.0000259 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.79
Solubility :	0.00416 mg/ml ; 0.0000161 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.67
Solubility :	0.000554 mg/ml ; 0.00000214 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.83

Safety of [ 28920-43-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 28920-43-6 ]

* 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 [ 28920-43-6 ]
Downstream synthetic route of [ 28920-43-6 ]

[ 28920-43-6 ] Synthesis Path-Upstream 1~3

1
[ 53940-82-2 ]
[ 28920-43-6 ]
[ 616867-28-8 ]

Reference： [1] Helvetica Chimica Acta, 1995, vol. 78, # 3, p. 563 - 580

2
[ 1197-17-7 ]
[ 28920-43-6 ]
[ 188715-40-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: With sodium carbonate In 1,4-dioxane; water at 20℃; for 2.5 h; Stage #2: With hydrogenchloride In 1,4-dioxane; water	Step 1: Dissolve 4-Aminomethyl-cyclohexanecarboxylic acid ((39); 1.15g, 7.30mmol) in 1,4-dioxane (12.0mL) and 10percent aqu. Na2CO3 (23.2mL) and add Fmoc-Cl (2.26g, 8.76mmol). Stir the reaction mixture for 2.5h at rt. Add 1M aqu HCl (42.0mL) to the mixture and extract with EtOAc (3 times). Wash the combined organic layers with 1M aqu HCl, water and brine, extract the combined aqu layers once again with EtOAc, dry the combined organic layers with Na2SO4 and remove solvent under reduced pressure. The left crude product is washed with ice cold EtOAc and dried in oil pump vacuum to obtain (40) as a white solid (2.28g, 83percent). No further purification. [M. Nichifor; E. H. Schacht; Tetrahedron;1994; 50; 12; 3747-3760]. 1H NMR (400MHz, CDCl3): 0.87-1.02 (br.m, 2 H); 1.34-1.52 (br.m, 4 H); 1.81 (br.d, 2 H, J 6Hz); 1.90-2.11 (br.s, 1 H); 2.12-2.35 (br.m, 1 H); 3.03 (Ψt, 2 H, J = 6.2Hz); 4.19 (br.Ψt, 1 H, J = 6.5Hz); 4.42 (br.Ψd, 2 H, J = 6.5Hz); 4.74 (br.s, 1 H); 7.30 (Ψt, 2 H, J = 7.4Hz); 7.38 (Ψt, 2 H, J = 7.4Hz); 7.57 (d, 2 H, J = 7.4Hz); 7.75 (d, 2 H, J = 7.4Hz).

Reference： [1] Patent: EP1577289, 2005, A1, . Location in patent: Page/Page column 23
[2] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884

3
[ 6168-72-5 ]
[ 28920-43-6 ]
[ 851678-69-8 ]

Reference： [1] European Journal of Organic Chemistry, 2007, # 35, p. 5826 - 5833

[ 28920-43-6 ] Synthesis Path-Downstream 1~10

1
[ 2566-30-5 ]
[ 28920-43-6 ]
[ 77128-73-5 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 4615 - 4625
[2]Biochemistry,2010,vol. 49,p. 2177 - 2185

2
[ 28920-43-6 ]
[ 121148-00-3 ]
(2S,4R)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 15017 - 15030

3
[ 63-91-2 ]
[ 28920-43-6 ]
[ 74-88-4 ]
[ 77128-73-5 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 7307 - 7310

4
[ 50595-15-8 ]
[ 28920-43-6 ]
Fmoc-glycolic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 0 - 20℃; for 24h;	Tert-butyl 2-hydroxy-acetate (2.5 g) was dissolved in a mixture of pyridine (15 ml) and dichloromethane (DCM, 30 ml). Then Fmoc-chloride (5 g) in dry DCM (15ml) was added dropwise at 0 C. The reaction mixture was stirred at room temperature for 24 hours. The solvent was removed under vacuum and the residue was redissolved in DCM (40 ml), washed with 1M sodium bicarbonate solution (20 mL) twice, brine solution (20 ml) twice, dried over anhydrous magnesium sulfate and concentrated. The obtained Fmoc-glycolic acid tert-butyl ester (4 g) was dissolved in trifluoroacetic acid (TFA), triisopropylsilane (TIS) and water (95/2.5/2.5, v/v/v, 15 mL) and stirred for 120 min. The solvent was removed under vacuum and the viscous residue was redissolved in 5% sodium bicarbonate solution (150 ml), washed with diethyl ether (75 ml) 3 times. The aqueous solution was then mixed with ethyl acetate (45 mL) and acidified with 40% phosphoric acid to pH = 2 at 0 C. The organic layer was collected and dried with anhydrous magnesium sulfate. The solvent was removed under vacuum to give the final product Fmoc-glycolic acid (Fmoc-GA).
	With pyridine; In dichloromethane; at 0 - 20℃; for 24h;	Tert-butyl 2-hydroxy-acetate (2.5 g) was dissolved in a mixture of pyridine (15 ml) and dichloromethane (DCM, 30 ml). Then Fmoc-chloride (5 g) in dry DCM (15ml) was added dropwise at 0 C. The reaction mixture was stirred at room temperature for 24 hours. The solvent was removed under vacuum and the residue was redissolved in DCM (40 ml), washed with 1M sodium bicarbonate solution (20 mL) twice, brine solution (20 ml) twice, dried over anhydrous magnesium sulfate and concentrated. The obtained Fmoc-glycolic acid tert-butyl ester (4 g) was dissolved in trifluoroacetic acid (TFA), triisopropylsilane (TIS) and water (95/2.5/2.5, v/v/v, 15 mL) and stirred for 120 min. The solvent was removed under vacuum and the viscous residue was redissolved in 5% sodium bicarbonate solution (150 ml), washed with diethyl ether (75 ml) 3 times. The aqueous solution was then mixed with ethyl acetate (45 mL) and acidified with 40% phosphoric acid to pH = 2 at 0 C. The organic layer was collected and dried with anhydrous magnesium sulfate. The solvent was removed under vacuum to give the final product Fmoc-glycolic acid (Fmoc-GA).

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 4088 - 4089
[2]Tetrahedron Letters,2016,vol. 57,p. 3635 - 3638
[3]Patent: WO2019/170895,2019,A1 .Location in patent: Paragraph 25; 26
[4]Patent: WO2019/170918,2019,A1 .Location in patent: Page/Page column 24; 25

5
[ 5467-57-2 ]
[ 28920-43-6 ]
[3-(aminomethyl)phenyl]boronic acid [ No CAS ]
[ 1165800-56-5 ]

Yield	Reaction Conditions	Operation in experiment
		2-Chloroquinoline-4-carboxylic acid (0.15 g, 0.72 mmol), 4-(aminomethylphenyl)boronic acid (0.16g, 0.87 mmol, 1.2 eq.) and Pd(PPh3)4 (42 mg, 0.036 mmol, 0.05 eq.) were added to a mixture of dioxane (2 mL) and a IM aq. solution OfK2CO3 (2 mL). The reaction mixture was degassed, sealed, and heated in the microwave at 140 0C for 15 min. The reaction mixture was cooled to 0 0C and a solution of (9-fiuorenylmethyl)chloro formate (0.46 g, 1.8 mmol) in dioxane (1 mL) was added dropwise. The reaction mixture was warmed to rt and stirred for 36 h. The reaction mixture was filtered and the solid was washed with DMSO, water and MeOH to give 2-[4-([(9H-fluoren-9-ylmeth- oxy)carbonyl]amino}methyl)phenyl]-quinoline-4-carboxylic acid (0.22 g, 60percent over two steps) as a crude solid, which was used directly in the next step without further purification, m/z 501.3 (M+eta)+.The crude 2-[4-([(9H-fluoren-9-ylmethoxy)carbonyl]-amino}methyl)phenyl]quinoline-4- carboxylic acid was reacted with tert-butyl [?ralpha"5f-4-(aminomethyl)cyclohexyl]methyl}- carbamate using essentially the same procedure as described for Example 1 (Method 1) to give the crude 9H-fluoren-9-ylmethyl [4-(4-[(?ralpha"5f-4-[(?ert-butoxycarbonyl)amino]- methyl} cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzyl]carbamate, which was used in the next step with no further purification, m/z 725.4 (M+eta)+.The crude 9H-fluoren-9-ylmethyl [4-(4-[(?ralpha"5f-4-[(?ert-butoxycarbonyl)amino]methyl}- cyclohexyl)methyl]carbamoyl}quinolin-2-yl)benzyl]carbamate (0.14 g, 0.19 mmol) was dissolved in DCM (4 mL) and treated with piperidine (1 mL). The reaction mixture was stirred at rt for 5 min. The reaction mixture was concentrated in vacuo to leave a residue. The residue was dissolved in DMSO and purified by etaPLC (Standard method D) to give <n="136"/>the title compound (35 mg, 32percent). 1R NMR (400 MHz, DMSO-J6) delta 8.77 (t, IH), 8.21 (d, 2H), 8.10-8.05 (m, IH), 8.03 (s, IH), 7.77 (t, IH), 7.61-7.46 (m, 4H), 6.74 (t, IH), 3.77 (s, 2H), 3.19 (t, 2H), 2.74 (t, 2H), 1.83 (s, 2H), 1.79 (d, 2H), 1.68 (d, 2H), 1.55-1.45 (m, IH), 1.33 (s, 9H), 1.30-1.23 (m, IH), 1.00-0.76 (m, 4H); m/z 503.4 (M+H)+.

Reference： [1]Patent: WO2009/82346,2009,A1 .Location in patent: Page/Page column 134-135

6
[ 1208119-54-3 ]
[ 28920-43-6 ]
[ 77128-73-5 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1386 - 1392

7
[ 28920-43-6 ]
[ 77128-73-5 ]

Reference： [1]Tetrahedron,2012,vol. 68,p. 6186 - 6192

8
[ 28920-43-6 ]
[ 183673-71-4 ]
[ 183673-66-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium carbonate; In tetrahydrofuran; at 0 - 25℃; for 12h;	4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert- butoxycarbonyl)piperidine-4-carboxylic acid (Scheme 1, compound 8) [0225] A solution of 4-amino-1 -(terf-butoxycarbonyl)piperidine-4- carboxylic acid (5 g, 20.5 mmol) in THF (300 mL) and Na2CO3 (6.45 g, 61 .5 mmol, 3.0 eq in 64.5 mL of water) was cooled to 0C before the dropwise addition of a solution of Fmoc chloride (5.3 g, 30.7 mmol, 1 .5 eq) in THF (30 mL). The resulting mixture was slowly warmed to 25C and stirred for an additional 12 hours. Upon completion, the reaction contents were carefully acidified with HCI (1 M), and the crude material was extracted with EtOAc (three times). The combined organic layers were dried (Na2SO4), concentrated, and the crude material was purified by combiflash 0 to 10% MeOH in DCM to provide 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1 -(te/t- butoxycarbonyl)piperidine-4-carboxylic acid (Scheme 1 , compound 8) (4.02 g, 42% yield). [0226] 1 H NMR (400 MHz, Ch lore-form -c/) delta 7.75 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.45-7.34 (m, 2H), 7.30 (td, J = 6.9, 6.3, 1 .4 Hz, 2H), 4.68-4.26 (m, 2H), 4.19 (t, J = 6.5 Hz, 1 H), 3.96-3.65 (m, 3H), 3.08 (s, 2H), 1 .91 -1 .77 (m, 2H), 1 .48 (s, 9H). 13C NMR (101 MHz, CDCI3) 177.19, 154.73, 143.67, 141 .32, 127.72, 127.08, 124.95, 1 19.97, 80.06, 67.90, 66.86, 57.49, 47.19, 31 .98, 28.42, 25.57. HRMS (m/z): [M+] cald for C26H30N2O6, 466.53, found 466.2

Reference： [1]Organic Syntheses,2005,vol. 81,p. 213 - 224
[2]Patent: WO2015/184349,2015,A2 .Location in patent: Paragraph 0225-0226

9
[ 28920-43-6 ]
[ 183673-71-4 ]
4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2015/184349,2015,A2

10
[ 28920-43-6 ]
4-bromo-2-chloro-3-methylbenzaldehyde [ No CAS ]
[ 192130-34-0 ]
tert-butyl 4-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)(4-bromo-2-chloro-3-methylbenzyl)amino)ethyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 59A tert-butyl 4-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)(4-bromo-2-chloro-3-methylbenzyl)amino)ethyl)piperazine-1-carboxylate To a mixture of Example 10A (3.13 g) in dichloromethane (143 mL) with <strong>[192130-34-0]tert-butyl 4-(2-aminoethyl)piperazine-1-carboxylate</strong> (3.69 g) was added acetic acid (3.84 mL), sodium cyanoborohydride (1.685 g) and methanol (35.7 mL). The mixture was stirred at ambient temperature for 30 minutes. 9-Fluorenylmethyl chloroformate (4.16 g) was added and stirring was continued for another hour. Triethylamine (15 mL) was added, and the material that formed were redissolved with methanol (50 mL). The resulting mixture was concentrated onto silica gel and purification by silica gel chromatography on a CombiFlash? Teledyne Isco system using a Teledyne Isco RediSep? Rf gold 220 g silica gel column (eluting with 0-70percent ethyl acetate/heptane) provided the title compound. LC/MS (APCI) m/z 670.1 (M+H)+.

Reference： [1]Patent: US2019/55264,2019,A1 .Location in patent: Paragraph 0741

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Technical Information

? Acyl Group Substitution ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Hydride Reductions ? Preparation of Aldehydes and Ketones ? Reactions of Amines ? Rosenmund Reduction ? Specialized Acylation Reagents-Ketenes

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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

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[ CAS No. 28920-43-6 ] {[proInfo.proName]}

Quality Control of [ 28920-43-6 ]

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Calculated chemistry of [ 28920-43-6 ] Expand+

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[ 28920-43-6 ] Synthesis Path-Upstream 1~3

[ 28920-43-6 ] Synthesis Path-Downstream 1~10

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