[ CAS No. 347174-05-4 ] {[proInfo.proName]}

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Quality Control of [ 347174-05-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 347174-05-4 ]

SDS Specification

Alternatived Products of [ 347174-05-4 ]

Product Details of [ 347174-05-4 ]

CAS No. :	347174-05-4	MDL No. :	MFCD08072959
Formula :	C₁₅H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJHBVMHOBZBWMX-UHFFFAOYSA-N
M.W :	262.34	Pubchem ID :	4068248
Synonyms :	Fer-1	Chemical Name :	Ethyl 3-amino-4-(cyclohexylamino)benzoate

Safety of [ 347174-05-4 ]

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 [ 347174-05-4 ]

* 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.

Downstream synthetic route of [ 347174-05-4 ]

[ 347174-05-4 ] Synthesis Path-Downstream 1~14

1
[ 1121-60-4 ]
[ 347174-05-4 ]
[ 390815-31-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With Oxone; In DMF (N,N-dimethyl-formamide); water; at 20℃; for 1h;	The diamine from above (3.20 g, 12.2 mmol) was dissolved in DMF (15 mL) and water (0.5 mL). 2-Pyridine carboxaldehyde (1.45 mL, 15 mmol) was added followed by oxone (0.65 equivalent, 8 mmol, 4.92 g). The mixture was stirred 1 h at room temperature. Water (60 mL) was added, and the pH of the reaction mixture was brought up to 9 by addition of 1 N NaOH. The brown precipitate that formed was collected by filtration, washed with water and dried. The crude benzimidazole ethyl ester was obtained in 80% yield (3.43 g).

Reference： [1]Synthesis,2003,p. 1683 - 1692
[2]Patent: US2003/236251,2003,A1 .Location in patent: Page 20

2
[ 10200-59-6 ]
[ 347174-05-4 ]
ethyl 1-cyclohexyl-1H-benzimidazole-5-carboxylate [ No CAS ]

Reference： [1]Synthesis,2003,p. 1683 - 1692

3
[ 87815-77-8 ]
[ 347174-05-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium(II) hydroxide/carbon; In methanol; under 760.051 Torr; for 72h;	The nitro derivative from above (24.28 g, 83 mmol) was hydrogenated (1 atm H2) over 20% Pd(OH)2 on carbon (200 mg) in MeOH (150 mL) for 3 days. The catalyst was removed by filtration and volatiles removed under reduced pressure to give the title diamine (21.72 g, 100% yield) as a dark purple solid.
85%	With 10% palladium hydroxide on charcoal; hydrogen; In methanol; at 20℃; for 17h;	General procedure B (hydrogenolysis) [0274] The ethyl 4-(substituted-amino)-3-nitrobenzoates (130 mg, 0.445 mmol) were dissolved in MeOH (10 mL) and hydrogenated (H2 gas) over 10% Pd(OH)2 on charcoal (90 mg) for 17 hours at room temperature. The solution was filtered through a pad of celite, and volatiles were removed under vacuum. The residue was purified by flash-column chromatography on silica gel to provide the desired Ferrostatin-1 derivatives. General procedure C (reductive amination reaction) (Abdel-Magid et al., 1996)
	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; under 1551.49 Torr; for 6h;	Step 8: 3-Amino-4-cyclohexylamino-benzoic acid ethyl ester (Compound 11); [02281 To a solution of 5.84 g (20 mmol) of Compound 10 in 50 mL ethyl acetate and 30 mL methanol, 100 mg of 10% Pd/C was added, and the mixture was hydrogenated at 30 psi for 6 h. The catalyst was removed by filtration through a pad of Celite, the solvent was evaporated to dryness resulting in a dark purple solid which was recrystallized from ether-hexane. The mother liquid was evaporated, and the resulting solid was suspended in hexane and filtered to give additional yield of Compound 11 [02291 MS: 263.18 (M+H) ; H1-NMR (CDCL3): No.(PPM) 7.57-7. 54 (dd, 1H, J=8.7 and 2.1 Hz, Ar-H6), 7. 39 (d, 1H, J=2. 1HZ, AR-H2), 6.57 (d, 1H, J=9.0 Hz, Ar- H5), 4.29 (q, 2H, J=7. 2Hz, CH2), 3.32 (M, 1H,-CH=), 2.05 (M, 2H), 1.77 (M, 2H), 1.66 (M, 2H), 1.42-1. 20 (M, 7H);

	With hydrogen; cyclohexene;palladium on activated carbon; In ethanol; at 83℃; for 3h;	Step 2: 3-Amino-4-cyclohexylaminobenzoic acid, ethyl ester In a 250 mL round bottom flask ethyl 4-(cyclohexylamino)-3-nitrobenzoate (3.01 g, 0.0103 mol) was dissolved in ethanol (40 mL) and 1 gram of 5% palladium on carbon (54.62% water) was added. Cyclohexene (7 mL, 0.07 mol) was then added and the reaction heated at 83 C. for 3 hours. The reaction mixture was filtered through celite and the filter cake washed with ethanol. The combined filtrates were concentrated to give 2.3 g title compound as a brownish tan solid. MS (ESI (+)m/z): 263.11 (M+H+).
	With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; water; at 20℃; for 17h;	General procedure: The ethyl 4-(substituted-amino)-3-nitrobenzoates and derivatives (the nitro compounds 3) (1 equiv.) were dissolved in MeOH (10 mL) and hydrogenated (H2 gas) over 10% Pd(OH)2 on charcoal for 17h at room temperature. The solution was filtered through a pad of celite and volatiles were removed under vacuum. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM:MeOH (20:1), to providethe desired AA1-AA8 derivatives (Table 1).

Reference： [1]Patent: US2003/236251,2003,A1 .Location in patent: Page 20
[2]Synthesis,2003,p. 1683 - 1692
[3]Journal of the American Chemical Society,2014,vol. 136,p. 4551 - 4556
[4]Patent: WO2015/84749,2015,A1 .Location in patent: Paragraph 0274; 0280
[5]Patent: WO2005/121132,2005,A1 .Location in patent: Page/Page column 40
[6]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1859 - 1863
[7]Patent: WO2005/12288,2005,A1 .Location in patent: Page/Page column 87; 127
[8]Patent: US2011/152260,2011,A1 .Location in patent: Page/Page column 16
[9]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5315 - 5320

4
[ 498-60-2 ]
[ 347174-05-4 ]
[ 871930-30-2 ]