156866-52-3|tert-Butyl 4-formylbenzylcarbamate| Ambeed

Structure of 156866-52-3

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Quality Control of [ 156866-52-3 ] Purity: 97% SDS Specification

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Product Details of [ 156866-52-3 ]

CAS No. :	156866-52-3
Formula :	C₁₃H₁₇NO₃
M.W :	235.28
SMILES Code :	O=C(OC(C)(C)C)NCC1=CC=C(C=O)C=C1
MDL No. :	MFCD06659090
Boiling Point :	No data available
InChI Key :	HRJJBEIFHFVBRT-UHFFFAOYSA-N
Pubchem ID :	2794832

Safety of [ 156866-52-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 156866-52-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	6
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	65.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.4 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.56
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.37
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.72
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.27
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.16

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.35
Solubility	1.04 mg/ml ; 0.00442 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.68
Solubility	0.496 mg/ml ; 0.00211 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.71
Solubility	0.046 mg/ml ; 0.000195 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.39 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.72

Application In Synthesis of [ 156866-52-3 ]

* 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 [ 156866-52-3 ]

[ 156866-52-3 ] Synthesis Path-Downstream 1~35

1
[ 123986-64-1 ]
[ 156866-52-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With manganese(IV) oxide; In dichloromethane; for 3h;	4- Butoxycarbonylaminomethyl-benzaldehyde, 8.8Alcohol 7 (2.20 g, 9.2 mmol) was dissolved in DCM (100 ml) and Mn02 (8.18 g, 92 mmol, 10 eq) was added and the resulting suspension was stirred for 3 hours. The reaction mixture was then filtered through celite and evaporated to yield Error. Reference source not found, as a white solid (2.18 g, 9.2 mmol, 100%). Rr = 0.62 (DCM / Ethyl acetate, 9 : 1); vmax = cm"1; NMR (300 MHz, CDC13) delta = 10.0 (CHO), 7.85 (d, 3J(H,H) = 8.1 Hz, 2H, ArCH a to CHO), 7.45 (d, 3J(H,H) = 8.1 Hz, 2H, ArCH a to CH2NHBoc), 4.99 (bs, 1 H, NHBoc), 4.40 (d, 3J(H,H) - 5.7 Hz, 2H, CH2NHB0C), 1.47 (s, 9H, C(C¾)3); 13C NMR (75 MHz, CDCI3) 6 =191.9 (CHO), 155.9 (CO), 145.9 (ArCCH2NHBoc), 135.5 (ArCCHO), 130.1 (ArCH a to CHO), 127.6 (ArCH a to CH2NHBoc), 85.1 (C(CH3)3), 44.3 (CH2NHBoc), 28.3 (C(CH3)3); HRMS (ESI+): m/z calculated for CnHi9N03Na [M + Na]+ : 258.1 101, found 258.1094. NMR data consistent with published data.6
100%	With Dess-Martin periodane; In dichloromethane; at -78 - 20℃; for 3h;	(4-Hydroxymethyl~benzyl)-carbamic acid tert-butyl ester (480 mg, 0.71 mmol) was dissolved in DCM (3 ml_) and cooled to -78 0C (dry ice / acetone). Dess-Martin periodinane (331 mg, 0.78 mmol) was added to the reaction which was allowed to warm to r.t and stir for 3 h. A 1 :1 solution of saturated sodium bicarbonate and sodium sulfite (20 ml_) was added and the reaction mixture stirred vigorously for 15 min. The organic layer was isolated, washed with saturated sodium bicarbonate (10 ml_), dried (Na2SO4) and evaporated to dryness to afford the desired compound (480 mg, 100%). m/z 258 [M++Na]+
97%	With manganese(IV) oxide; In dichloromethane; at 20℃; for 3.5h;	Step D) FORTNCTTION of (N-Boc-4-aminomethyl)benzaldehyde; To a suspension of MiO2 (600 g) in dry DCM (3 L) was added a solution of N-BOC- (4- hydroxymethyl) benzylamine (90 g) in 500 mL of DCM at rt over 30 min and allowed to stir 3 H. THE reaction mixture was filtered and filtrate concentrated under vacuum to give the title compound (88 G, 97%).

87%	With manganese(IV) oxide; In chloroform; at 20℃;	Boc2O was added in one portion at r.t. to a solution of (4-aminomethyl-phenyl)-methanol Compound 3a (21.2 mmol, 2.9 g) in CH2C12 (100 mL). The resulting solution wasstirred for 48h, then washed with a 10% citric acid solution (50 mL) followed by brine. Theorganic layer was separated, then dried over Na2SC>4 and filtered. The solvent was removed invacua to obtain <strong>[123986-64-1](4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester</strong> Compound 3b as awhite solid (5.2 g, 99% yield), which was used in the next step without further purification.MnO2 (9.6 g) was added to a solution of Compound 3b (21.2 mmol, 5.2 g) inchloroform (60 mL), forming a black suspension that was stirred at r.t. overnight then filteredthrough a pad of celite. The solvent was evaporated in vacua to obtain (4-forinyl-benzyl)-carbamic acid tert-butyl ester Compound 3c as a white solid (4.3 g, 87% yield), which was usedin the next step without purification.; NaB(OAc)3H (2.8 mmol, 0.58 g) was added to a mixture of Compound 3c (2.6 mmol,0.6 g) and tetrahydro-pyran-4-ylamine Compound 3d (2.6 mmol, 0.26 g) in CH2C12 (25 mL)and the resulting suspension was stirred at r.t. An aliquot of the reaction mixture showed theformation of product (MS m/e 321; 100%). An aqueous solution of formaldehyde (37%solution, 8.6 mmol, 0.7 mL) was added to the reaction mixture, followed by NaB(OAc)3H (2.8mmol, 0.58 g) added in one portion under ice cooling. The reaction mixture was stirred at r.t.for about 2h, then made basic with a 2N NaOH solution and extracted with CH2C12. Theorganic layer was washed with brine, then separated and dried over Na2SO4. The drying agentwas filtered and the solvent was removed in vacua to yield (4-[methyl-(tetrahydro-pyran-4-yl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester Compound 3e as a pale yellow oil.MS m/e 235 (M+H, 100%). The product was purified by column chromatography (4:1CH2Cl2:MeOH) to yield a colorless oil (0.52 g, 59% yield).; Compound 3e was dissolved in CH2Cl2, then HC1 in dioxane was added and themixture was stirred at r.t. for 12 hrs. The solvent was removed and the gummy residue wasmade basic with 2N NaOH and extracted with EtOAc. The organic layer was washed withbrine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent wasremoved in vacua to obtain (4-aminomethyl-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineCompound 3f as a pale yellow oil (0.3 g, 83% yield). MS m/e 235 (M+H, 100%).; A solution of 3-(3-trifluoromethyl-phenyl)-acryloyl chloride Compound 3g (0.3 mrnol,0.07 g) in THF (2 mL) was added dropwise to a solution of Compound 3f (0.2 mmol, 0.05 g)and Et3N (0.8 mmol, 0.14 mL) in THF (10 mL) at 0C. The resulting suspension was allowedto warm to r.t. overnight. The reaction mixture was made basic with a 2N NaOH solution andextracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2X10 mL) andthe organic layers were washed with brine, then dried over Na2SO4 and filtered. The solventwas removed in vacua to yield a yellow solid (with methane) as the product. The crude productwas purified by preparative TLC (9:1 EtOAc-.MeOH, Rf = 0.2) to yield N-(4-[methyl-(tetrahydro-pyran-4-yi)-amino]-methyl}-benzyi)-3-(3-trifluoromethyl-phenyl)-acrylamideCompound 3h (0.06 g, 49% yield). MS m/e 433 (M+H, 100%).; Mel (0.08 mL, 1.28 mmol) was added dropwise to a solution of Compound 3h (0.07mmol, 0.03 g) in a mixture of acetone:acetonitrile (2 mL). The resulting solution was stirred atr.t. for 24h to provide a residue. The residue was washed with ether (2x 1 mL) and dried undera high vacuum to provide Compound 64 (0.04 g, 93% yield) as an iodide salt. MS m/e 584(M+H, 100%).
87%	With manganese(IV) oxide; In chloroform; at 20℃;	MnO2 (9.6 g) was added to a solution of Compound 3b (21.2 mmol, 5.2 g) in chloroform (60 mL), forming a black suspension that was stirred at r.t. overnight then filtered through a pad of celite. The solvent was evaporated in vacuo to obtain (4-formyl-benzyl)-carbamic acid tert-butyl ester Compound 3c as a white solid (4.3 g, 87% yield), which was used in the next step without purification.
80%	With manganese(IV) oxide; In dichloromethane; at 20℃; for 16h;	Stage 3 - Alcohol oxidation; Stage 2 product (5.87g, 24.73mmol) was stirred in DCM (20OmL) with MnO2 (16.71g, 192.20mmol) for 16h at RT. The reaction was then filtered through celite and the solvent removed in vacuo to give the product as a yellow oil which was used in the next step without further purification (4.63g, 80%). m/z = 258 [M+Na]+.
80%	With manganese(IV) oxide; In dichloromethane; at 20℃; for 16h;	Stage 3 - Preparation of te/t-butyl (4-formylbenzyl)carbamate; Stage 2 product (5.87g, 24.73mmol) was stirred in DCM (20OmL) with MnO2 (16.71g, 192.2mmol) for 16h at RT. The reaction was then filtered through celite and the solvent removed in vacuo to give the product as a yellow oil (4.63g, 80%). m/z = 258 [M+Na]
70%	With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 25℃; for 1h;	To a solution of (4-Hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (4.5 g, 18.2 mmol) in dichloromethane (45 ml) were added PCC (4.07 g, 18.2 mmol), sodium acetate (0.26 g, 3.2 mmol) and the mixture was stirred at 25 C over a period of 60 min. The resulting mixture was diluted with ethyl acetate (200 mL) and it was stirred for 30 min. Then the reaction mixture filtered through Buchner funnel, filtrate was washed with water (2X50 mL) and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain (4-Formyl-benzyl)-carbamic acid tert-butyl ester as a pale yellow solid(3.0 g, 70 %).
70%	With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 25℃; for 1h;	To a solution of (4-Hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (4.5 g, 18.2 mmol) in dichloromethane (45 ml) were added PCC (4.07 g, 18 2 mmol), sodium acetate (0.26 g, 3.2 mmol) and the mixture was stirred at 25 C. over a period of 60 min. The resulting mixture was diluted with ethyl acetate (200 mL) and it was stirred for 30 min. Then the reaction mixture filtered through Buchner funnel, filtrate was washed with water (2*50 mL) and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain (4-Formyl-benzyl)-carbamic acid tert-butyl ester as a pale yellow solid (3.0 g, 70%).
	manganese(IV) oxide; In chloroform; at 20℃; for 15h;	The compound (18.0 g) obtained in Example 103-2 was dissolved in chloroform (540 ml) and then added with manganese dioxide (chemically processed product) (118 g), followed by stirring at room temperature for 15 hours. The reaction solution was filtrated through Celite and the filtrate was then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (17.1 g) as a white solid.
	With manganese(IV) oxide; In chloroform; for 1h;Heating / reflux;	Reference Example 64 tert-Butyl 4-formylbenzylcarbamate Manganese dioxide (1.22 g) was added to a chloroform solution (20 ml) of tert--butyl 4-hydroxymethylbenzylcarbamate (1.22 g), followed by heating under reflux for 1 hour. After celite filtration, the filtrate was concentrated, the thus obtained residue was purified by silica gel column chromatography, and the fraction obtained from the elude of n-hexane:ethyl acetate = 2:1 was concentrated under reduced pressure to obtain the title compound (965 mg) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 1.46 (9H, s), 4.39 (2H, d, J=5.6 Hz), 5.16 (1H, bs), 7.44 (2H, d, J=8.1 Hz), 7.81 (2H, d, J=8.1 Hz), 9.98 (1H, s). ESI-MS m/z: 236 (M+H)+.
	With manganese(IV) oxide; In chloroform; at 20℃;	The compound (17.6 g) obtained in Example 23-2 was dissolved in chloroform (400 ml) and then added with manganese dioxide (chemically processed product) (88.2 g) and the whole was stirred overnight at room temperature. After completion of the reaction, the resultant was filtrated through Celite. The solvent was distilled off, thereby obtaining the subject compound (20.4 g) as a colorless crystal.
	With manganese(IV) oxide; In ethyl acetate; at 20℃; for 1h;	Example 3 tert-butyl (4-formylbenzyl)carbamate To an ethyl acetate (50 mL) solution of tert-butyl [4-(hydroxymethyl)benzyl]carbamate (3.0 g), manganese dioxide (20.0 g) was added. The reaction solution was stirred at room temperature for one hour. The reaction solution was filtered through celite (trade name). The filtrate was conentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 8: 2 ? 7: 3) to obtain the title compound having the following physical properties (2.3 g). Rf 0.83 (chloroform: methanol = 9: 1); NMR (CDCl3): delta 1.47 (s, 9H), 4.40 (m, 2H), 4.95 (m, 1H), 7.45 (d, J = 7.8 Hz, 2H), 7.86 (d, J = 7.8 Hz, 2H), 10.00 (s, 1H).
	With Dess-Martin periodane; In dichloromethane; at 20℃; for 2.5h;	Dess-Martin periodinane (1.25 eq) was added to a flask with a stir bar. Diluted with DCM (0.25 M), and the resulting slurry was stirred vigorously at roomtemperature. Added a solution of alcohol (1.00 eq) in DCM (0.20 M) in dropwise fashion, and the resulting reaction mixture was stirred vigorously under Ar at room temperature. After 2.5 hrs, TLC indicated complete conversion of starting material. The reaction mixture was poured over a 1:1 mixture of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3 (55 mL per mmol alcohol). The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. A solution ofamine (1.00 eq) in DCM (0.12 M) was added to a flask with a stir bar. Added a solution of aldehyde (1.05 eq) in DCM (0.53 M), and the resulting mixture was stirred under Ar at room temperature for 5 mm. After this time, acetic acid (1.00 eq) was added, and the resulting mixture was stirred under Ar at room temperature for 15 mm. After this time, sodium triacetoxyborohydride (3.00 eq) was added, and the resulting reaction mixture was allowed to stir overnight at room temperature under Ar. In the morning, thereaction mixture was diluted with DCM and washed once with 1 M aqueous sodium hydroxide. The resulting aqueous layer was extracted 3 times with DCM. Combined organic layers were dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The cmde material was taken up in DCM (40 mL per mmol amine), filtered, and evaporated under reduced pressure.

References: [1]Patent: WO2012/95628,2012,A1 .Location in patent: Page/Page column 18-19.
[2]Patent: WO2006/117549,2006,A1 .Location in patent: Page/Page column 148.
[3]Patent: WO2005/12280,2005,A1 .Location in patent: Page/Page column 53.
[4]Patent: WO2006/12135,2006,A1 .Location in patent: Page/Page column 49-51.
[5]Patent: US2006/293379,2006,A1 .Location in patent: Page/Page column 63.
[6]Patent: WO2008/53131,2008,A1 .Location in patent: Page/Page column 58; 60.
[7]Patent: WO2008/40934,2008,A1 .Location in patent: Page/Page column 58-59.
[8]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.
[9]Tetrahedron Letters,2008,vol. 49,p. 6033 - 6035.
[10]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4356 - 4373.
[11]Patent: WO2011/21209,2011,A1 .Location in patent: Page/Page column 49; 50; 51.
[12]Patent: US2012/101099,2012,A1 .Location in patent: Page/Page column 18; 19.
[13]Tetrahedron,2002,vol. 58,p. 741 - 755.
[14]Patent: EP1550657,2005,A1 .Location in patent: Page/Page column 92.
[15]Patent: EP1612204,2006,A1 .Location in patent: Page/Page column 41.
[16]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 48.
[17]Journal of Medicinal Chemistry,2013,vol. 56,p. 5198 - 5202.
[18]Journal of Medicinal Chemistry,2018,vol. 61,p. 946 - 979.
[19]Patent: EP2042503,2009,A1 .Location in patent: Page/Page column 60.
[20]Patent: WO2018/156595,2018,A1 .Location in patent: Page/Page column 173; 174; 176.

2
[ 270563-62-7 ]
[ 156866-52-3 ]
C₁₅₇H₂₂₅N₉O₁₆ [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 741 - 755.

3
[ 141399-96-4 ]
[ 156866-52-3 ]
2-[1'-{4"-(tert-butoxycarbonylamino-methyl)-phenyl}-meth-(Z)-ylidene]-3-oxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 6033 - 6035.
[2]Organic letters,2003,vol. 5,p. 141 - 144.

4
[ 156866-52-3 ]
3-oxo-2,3-dihydro-benzo[<i>b</i>]thiophene-7-carboxylic acid methyl ester [ No CAS ]
2-[1-[4-(tert-Butoxycarbonylamino-methyl)-phenyl]-meth-(Z)-ylidene]-3-oxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid methyl ester [ No CAS ]

References: [1]Organic letters,2003,vol. 5,p. 141 - 144.

5
[ 101-02-0 ]
[ 621-84-1 ]
[ 156866-52-3 ]
[ 695171-96-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

6
[ 875582-80-2 ]
[ 156866-52-3 ]

References: [1]Synthesis,2005,p. 3297 - 3300.

7
[ 956928-36-2 ]
[ 156866-52-3 ]
[ 1018674-41-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 3h;	Stage 4 - Preparation of cyclopentyl (2S)-[(Lambda-[(tert- butoxycarbonyl)amino]methyl}benzyl)amino](cyclohexyl)acetate; Stage 3 product (650mg, 2.70mmol) was stirred in DCE (2OmL), Intermediate J1 (707mg,2.70mmol) and STAB (918mg, 4.33mmol) at RT under a nitrogen atmosphere for 3h. After this time the reaction was diluted with H2O (5OmL) and extracted with Et2O (2 x 10OmL). The combined organic extracts were dried (MgSO4) and solvent removed in vacuo to give the product as a brown oil (1.13g, 95percent). m/z = 445 [M+H]+.

References: [1]Patent: WO2008/40934,2008,A1 .Location in patent: Page/Page column 58-59.

8
[ 66739-89-7 ]
[ 156866-52-3 ]

References: [1]Synthesis,2005,p. 3297 - 3300.

9
[ 105-07-7 ]
[ 156866-52-3 ]

References: [1]Synthesis,2005,p. 3297 - 3300.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 5198 - 5202.

10
[ 104566-44-1 ]
[ 156866-52-3 ]

References: [1]Synthesis,2005,p. 3297 - 3300.

11
[ 56-91-7 ]
[ 156866-52-3 ]

12
[ 24424-99-5 ]
1.) NaH; 2.) SOCl₂ [ No CAS ]
[ 156866-52-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

13
[ 33233-67-9 ]
[ 156866-52-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.
[2]Patent: WO2011/21209,2011,A1 .
[3]Patent: US2012/101099,2012,A1 .
[4]Journal of the American Chemical Society,2012,vol. 134,p. 4465 - 4468.
[5]Patent: WO2013/106646,2013,A2 .
[6]Patent: US2014/356322,2014,A1 .
[7]Journal of Medicinal Chemistry,2018,vol. 61,p. 946 - 979.
[8]Patent: WO2006/117549,2006,A1 .
[9]Patent: WO2008/40934,2008,A1 .
[10]Patent: WO2018/156595,2018,A1 .

14
[ 156866-52-3 ]
[(4-aminomethyl-phenyl)-benzyloxycarbonylamino-methyl]-phosphonic acid diphenyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

15
[ 156866-52-3 ]
C₃₁H₃₉N₄O₇P [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

16
[ 156866-52-3 ]
C₃₄H₄₄N₅O₈P [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

17
[ 156866-52-3 ]
[ 695172-03-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

18
[ 156866-52-3 ]
[ 695172-10-2 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

19
[ 156866-52-3 ]
diphenyl N-(N-benzyloxycarbonyl-D-seryl-L-alanyl)amino-(4-guanylmethylphenyl)methanephosphonate trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

20
[ 156866-52-3 ]
[ 695172-17-9 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2411 - 2413.

21
[ 156866-52-3 ]
2-[1-[4-(tert-Butoxycarbonylamino-methyl)-phenyl]-meth-(E)-ylidene]-3-oxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid [ No CAS ]

References: [1]Organic letters,2003,vol. 5,p. 141 - 144.

22
[ 156866-52-3 ]
[ 875582-76-6 ]

References: [1]Organic letters,2003,vol. 5,p. 141 - 144.

23
[ 24424-99-5 ]
[ 156866-52-3 ]

References: [1]Tetrahedron,2002,vol. 58,p. 741 - 755.
[2]Patent: WO2011/21209,2011,A1 .
[3]Organic Letters,2011,vol. 13,p. 3956 - 3959.
[4]Patent: US2012/101099,2012,A1 .
[5]Journal of the American Chemical Society,2012,vol. 134,p. 4465 - 4468.
[6]Patent: WO2006/117549,2006,A1 .
[7]Patent: WO2008/40934,2008,A1 .

24
[ 39895-56-2 ]
[ 156866-52-3 ]

References: [1]Tetrahedron,2002,vol. 58,p. 741 - 755.
[2]Patent: WO2012/95628,2012,A1 .
[3]Journal of Medicinal Chemistry,2013,vol. 56,p. 5198 - 5202.
[4]Patent: WO2006/117549,2006,A1 .

25
[ 56-91-7 ]
[ 24424-99-5 ]
[ 156866-52-3 ]

Yield	Reaction Conditions	Operation in experiment
		[0261] To a solution of 5.0 g of 4-aminomethylbenzoic acid in 40 ml of dioxane-water (1:1) was added 6.0 g of NaHCO3 and a solution of 7.6 g of di-tertiary butyl dicarbonate in 20 ml of dioxane in order at room temperature, and the mixture was stirred at room temperature for 4 days. The solvent was distilled off under reduced pressure, and the residue was neutralized with aqueous hydrochloric acid. The precipitated solid was collected by filtration, and dried under reduced pressure to give 8.0 g of a carboxylic acid. The carboxylic acid (0.85 g) was dissolved in 10 ml of THF, to which was added 0.60 g of 1,1'-carbonylbis-1H-imidazole under ice-cooling, and the mixture was stirred at 50° C. for 40 minutes. To the resulting solution was added 0.43 g of N,O-dimethylhydroxylamine hydrochloride and 0.7 ml of triethylamine (Et3N) in order under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the mixture, and the mixture was extracted with ethyl acetate (EtOAc). The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 0.98 g of an amide. The amide (0.98 g) was dissolved in 10 ml of THF, to which was added 0.12 g of lithium aluminum hydride at -78° C., and the mixture was stirred at the same temperature for 40 minutes. There was added 2.0 g of Na2SO4.10H2O and the mixture was warmed up to room temperature and stirred for 3 hours. The reaction mixture was filtered and evaporated under reduced pressure to give 0.76 g of tertiary (t-)butyl 4-formylbenzylcarbamate.

References: [1]Patent: US2003/232860,2003,A1 .Location in patent: Page 13.

Yield	Reaction Conditions	Operation in experiment
99%		Step 3 Synthesis of 4-N-(1,1-dimethylethoxy-carbonyl)aminomethylbenzaldehyde (34) To a solution of 0.48 mL (5.48 mmol) of oxalyl chloride in CH2Cl2 (2 mL) was slowly added a solution of 0.63 mL (8.76 mmol) of DMSO in CH2Cl2 (2 mL) at -78° C. After 15 minutes, a solution of 520 mg (2.19 mmol) of compound 33 in CH2Cl2 (3 mL) was added slowly and the reaction mixture was stirred for 30 minutes. 2.5 mL of TEA was added slowly. The reaction mixture was warmed to room temperature. CH2Cl2 and H2O were added and organic layer was separated. The organic layer was washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by short flash column chromatography (silica, Hex:EtOAc=2:1) to give 510 mg (2.17 mmol) of compound 34 in 99percent yield. H NMR (CDCl3): 9.99 (s, 1H), 7.85 (d, J=7.9 Hz, 2H), 7.44 (d, J=7.9 Hz, 2H), 4.95 (br s, 1H), 4.40 (d, 2H), 1.47 (s, 9H); 13C NMR (CDCl3): 191.95, 156.01, 146.37, 135.24, 129.93, 127.53, 79.57, 44.13, 28.28
89%		b) 4-[N-(t-butoxycarbonyl)aminomethyl]benzaldehyde To a solution of the compound of Example 19(a) (4.0 g, 16.9 mmol) in dry dichloromethane (50 mL) was added manganese dioxide (10 g, 115 mmol). The mixture was stirred and refluxed for 16 h and filtered hot through a pad of Celite.(R). which was rinsed with dichloromethane. The filtrate was concentrated to give the title compound (3.55 g, 89percent) as a white solid. TLC Rf 0.45 (5percent methanol/chloroform); 1H NMR (CDCl3) delta1.49 (9H, s), 4.43 (2H, d, J=6 Hz), 5.15 (1H, br s), 7.51 (2H, d, J=8 Hz), 7.92 (2H, d, J=8 Hz), 10.10 (1H, s).

27
[ 141-82-2 ]
[ 156866-52-3 ]
[ 843675-70-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With piperidine; In pyridine; at 20 - 105℃; for 3h;	Step e) Formation of 4-(N-Boc aminomethyl) cinnamic acid; To a solution of (N-BOC-4-AMINOMETLIYL) BENZALDELIYDE (50 g, 0.212 mol) in pyridine (600 mL) was added malonic acid (55 g, 0. 53 mol) and piperidine (5 mL) with stirring at rt. The reaction mixture was allowed to reflux at 105°C for 3 h. The reaction mixture was cooled and concentrated under vacuum. The solid residue obtained was treated with 10percent aqueous citric acid solution. The solid was filtered, washed with cold water (2 L) and dried to give the title compound (58 G, 97percent).

References: [1]Patent: WO2005/12280,2005,A1 .Location in patent: Page/Page column 53.

28
[ 62146-62-7 ]
[ 156866-52-3 ]
[ 675138-10-0 ]

Yield	Reaction Conditions	Operation in experiment
		The compound (951.6 mg) obtained in Example 103-3 was dissolved in anhydrous methanol (38 ml) and added with (4-amino-butyl)-carbamic acid benzyl ester (898.0 mg) and trimethyl orthoformate (1.33 ml), followed by stirring at room temperature for 15.5 hours. After that, the solution was cooled with ice and added with sodium borohydride (458.5 mg), followed by stirring at room temperature for 1.5 hours. After the reaction, the solvent was distilled off and the residue was then added with water, followed by extraction with chloroform. The extract was washed with saturated saline solution and dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.1479 g) as a colorless oily substance. MS(FAB,Pos.):m/z=442[M+H]+

References: [1]Patent: EP1550657,2005,A1 .Location in patent: Page/Page column 92.

29
[ 110-91-8 ]
[ 156866-52-3 ]
[ 874888-96-7 ]

Yield	Reaction Conditions	Operation in experiment
		NaB(OAc)3H (0.82 mmol, 0.17 g) was added to a mixture of (4-formyl-benzyl)-carbamic acid tert-butyl ester Compound 3c (0.75 mmol, 0.17 g) and morpholine Compound 9a(0.75 mmol, 0.07 mL) in CH2C12 (20 mL) and the resulting suspension was stirred at roomtemperature for 6 hrs. The reaction mixture was basified with 2N NaOH solution and wasextracted with CH2C12. The organic layer was washed with brine, separated and dried overNa2SO4. The drying agent was filtered and the solvent was removed in vacua to a crudeproduct as a pale yellow oil. MS m/e 307 (M+H, 100percent), The product was purified by prepTLC (10:1 CH2Cl2/MeOH, Rf = 0.5) to yield (4-morpholin-4-ylmethyl-benzyl)-carbamic acidtert-butyl ester Compound 9b.; Compound 9b was dissolved in QHUClj and was stirred with HC1 in dioxane at r.t. for12 hrs. The solvent was removed to obtain a gummy residue, which was basified with 2NNaOH and extracted with EtOAc. The organic layer was washed with brine, separated anddried over Na2SO4. The drying agent was filtered and the solvent was removed in vacua toobtain 4-morpholin-4-ylmethyl-benzylamine Compound 9c as pale yellow oil (wt. 0.09 g, 58percentyield). MS m/e 207 (MH, 100percent).; A solution of 3-(3-trifluoromethyl-phenyl)-acryloyl chloride Compound 3g (0.3 mmol,0.07 g) in THF (2 mL) was added dropwise to a solution of Compound 9c (0.19 mmol, 0.04 g)and Et3N (0.8 mmol, 0.14 mL) in THF (10 mL) at 0°C. The resulting suspension was allowedto warm to r.t. overnight. The reaction mixture was basified with 2N NaOH solution and wasextracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2X10 mL).The organic layers were washed with brine, then dried over Na2SC>4 and filtered. The solventwas removed in vacua and the resulting yellow gummy oil was purified by preparative TLC(10:1 CH2Cl2/MeOH, Rf = 0.5) to yield N-(4-moipholin-4-ylmethyl-benzyl)-3-(3-trifluoromethyl-phenyl)-acrylamide Compound 9d as a pale yellow solid (0.06 g , 77percent). MSm/e 405 (M+H, 100percent).; Mel (1.28 mmol, 0.08 mL) was added dropwise to a solution of Compound 9d (0.07mmol, 0.03 g) in a mixture of acetone/acetonitrile (2 mL). The solution was stirred at roomtemperature for 24 hrs and concentrated. The resulting residue was washed with ether (2x1mL) and dried under high vacuum to give Compound 62 (0.03 g, 78percent). MS m/e 546 (M).
		NaB(OAc)3H (0.82 mmol, 0.17 g) was added to a mixture of (4-formyl-benzyl)-carbamic acid tert-butyl ester Compound 3c (0.75 mmol, 0.17 g) and morpholine Compound 9a (0.75 mmol, 0.07 mL) in CH2Cl2 (20 mL) and the resulting suspension was stirred at room temperature for 6 hrs. The reaction mixture was basified with 2N NaOH solution and was extracted with CH2Cl2. The organic layer was washed with brine, separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo to a crude product as a pale yellow oil. MS m/e 307 (M+H, 100percent). The product was purified by prep TLC (10:1 CH2Cl2/MeOH, Rf=0.5) to yield (4-morpholin-4-ylmethyl-benzyl)-carbamic acid tert-butyl ester Compound 9b.
		<strong>[156866-52-3](4-Formyl-benzyl)-carbamic acid tert-butyl ester</strong> Compound 15a (555 mg, 2.37 mmol, prepared as described in Far A R, Cho Y L, Rang A, Rudkewich D M, Rebek J, Tetrahedron, 2002, 58(4), 741-756) was added to a solution of morpholine (207 muL, 2.37 mmol) in MeOH (5 mL) and acetic acid (0.20 mL). The mixture was stirred for 1 hr and then 95percent NaBH3CN (198 mg, 3.0 mmol) was added. The reaction was diluted after 2 hr with saturated NaHCO3 and extracted with EtOAc to provide (4-morpholin-4-ylmethyl-benzyl)-carbamic acid tert-butyl ester Compound 15b (230 mg), isolated by flash chromatography as a white solid. MS 307 (MH+).

References: [1]Patent: WO2006/12135,2006,A1 .Location in patent: Page/Page column 63-64.
[2]Patent: US2006/293379,2006,A1 .Location in patent: Page/Page column 73.
[3]Patent: US2006/58341,2006,A1 .Location in patent: Page/Page column 38.

30
(4-methylsulfonyl)aniline hydrochloride [ No CAS ]
[ 156866-52-3 ]
C₂₀H₂₆N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[156866-52-3]tert-butyl N-(4-formylbenzyl)carbamate</strong> (45 mg, 0.2 mmol) and 4-methanesulfonylaniline hydrochloride (41 mg, 0.2 mmol) in 1 mL of methanol was stirred at room temperature for 30 min, then 0.15 mL of acetic acid was added, followed by 16 mg (0.24 mmol) of sodium cyanoborohydride. The reaction was complete in 5 h. The mixture was treated with saturated sodium bicarbonate solution until pH=8, then extracted with ethyl acetate twice. The combined organics were dried over MgSO4, filtered, and concentrated. The solid was dissolved in 1 mL of methylene chloride, followed by the addition of 0.1 mL of trifluoroacetic acid. The mixture was stirred at room temperature overnight, then concentrated to afford the titled compound as an oil.

References: [1]Patent: US2006/173050,2006,A1 .Location in patent: Page/Page column 71.

31
[ 38041-19-9 ]
[ 156866-52-3 ]
[ 874888-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃;	Boc2O was added in one portion at r.t. to a solution of (4-aminomethyl-phenyl)-methanol Compound 3a (21.2 mmol, 2.9 g) in CH2C12 (100 mL). The resulting solution wasstirred for 48h, then washed with a 10percent citric acid solution (50 mL) followed by brine. Theorganic layer was separated, then dried over Na2SC>4 and filtered. The solvent was removed invacua to obtain (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester Compound 3b as awhite solid (5.2 g, 99percent yield), which was used in the next step without further purification.MnO2 (9.6 g) was added to a solution of Compound 3b (21.2 mmol, 5.2 g) inchloroform (60 mL), forming a black suspension that was stirred at r.t. overnight then filteredthrough a pad of celite. The solvent was evaporated in vacua to obtain (4-forinyl-benzyl)-carbamic acid tert-butyl ester Compound 3c as a white solid (4.3 g, 87percent yield), which was usedin the next step without purification.; NaB(OAc)3H (2.8 mmol, 0.58 g) was added to a mixture of Compound 3c (2.6 mmol,0.6 g) and tetrahydro-pyran-4-ylamine Compound 3d (2.6 mmol, 0.26 g) in CH2C12 (25 mL)and the resulting suspension was stirred at r.t. An aliquot of the reaction mixture showed theformation of product (MS m/e 321; 100percent). An aqueous solution of formaldehyde (37percentsolution, 8.6 mmol, 0.7 mL) was added to the reaction mixture, followed by NaB(OAc)3H (2.8mmol, 0.58 g) added in one portion under ice cooling. The reaction mixture was stirred at r.t.for about 2h, then made basic with a 2N NaOH solution and extracted with CH2C12. Theorganic layer was washed with brine, then separated and dried over Na2SO4. The drying agentwas filtered and the solvent was removed in vacua to yield (4-[methyl-(tetrahydro-pyran-4-yl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester Compound 3e as a pale yellow oil.MS m/e 235 (M+H, 100percent). The product was purified by column chromatography (4:1CH2Cl2:MeOH) to yield a colorless oil (0.52 g, 59percent yield).; Compound 3e was dissolved in CH2Cl2, then HC1 in dioxane was added and themixture was stirred at r.t. for 12 hrs. The solvent was removed and the gummy residue wasmade basic with 2N NaOH and extracted with EtOAc. The organic layer was washed withbrine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent wasremoved in vacua to obtain (4-aminomethyl-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineCompound 3f as a pale yellow oil (0.3 g, 83percent yield). MS m/e 235 (M+H, 100percent).; A solution of 3-(3-trifluoromethyl-phenyl)-acryloyl chloride Compound 3g (0.3 mrnol,0.07 g) in THF (2 mL) was added dropwise to a solution of Compound 3f (0.2 mmol, 0.05 g)and Et3N (0.8 mmol, 0.14 mL) in THF (10 mL) at 0°C. The resulting suspension was allowedto warm to r.t. overnight. The reaction mixture was made basic with a 2N NaOH solution andextracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2X10 mL) andthe organic layers were washed with brine, then dried over Na2SO4 and filtered. The solventwas removed in vacua to yield a yellow solid (with methane) as the product. The crude productwas purified by preparative TLC (9:1 EtOAc-.MeOH, Rf = 0.2) to yield N-(4-[methyl-(tetrahydro-pyran-4-yi)-amino]-methyl}-benzyi)-3-(3-trifluoromethyl-phenyl)-acrylamideCompound 3h (0.06 g, 49percent yield). MS m/e 433 (M+H, 100percent).; Mel (0.08 mL, 1.28 mmol) was added dropwise to a solution of Compound 3h (0.07mmol, 0.03 g) in a mixture of acetone:acetonitrile (2 mL). The resulting solution was stirred atr.t. for 24h to provide a residue. The residue was washed with ether (2x 1 mL) and dried undera high vacuum to provide Compound 64 (0.04 g, 93percent yield) as an iodide salt. MS m/e 584(M+H, 100percent).
	With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃;	NaB(OAc)3H (2.8 mmol, 0.58 g) was added to a mixture of Compound 3c (2.6 mmol, 0.6 g) and tetrahydro-pyran-4-ylamine Compound 3d (2.6 mmol, 0.26 g) in CH2Cl2 (25 mL) and the resulting suspension was stirred at r.t. An aliquot of the reaction mixture showed the formation of product (MS m/e 321; 100percent). An aqueous solution of formaldehyde (37percent solution, 8.6 mmol, 0.7 mL) was added to the reaction mixture, followed by NaB(OAc)3H (2.8 mmol, 0.58 g) added in one portion under ice cooling. The reaction mixture was stirred at r.t. for about 2 h, then made basic with a 2N NaOH solution and extracted with CH2Cl2. The organic layer was washed with brine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo to yield (4-[methyl-(tetrahydro-pyran-4-yl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester Compound 3e as a pale yellow oil. MS m/e 235 (M+H, 100percent). The product was purified by column chromatography (4:1 CH2Cl2:MeOH) to yield a colorless oil (0.52 g, 59percent yield).

References: [1]Patent: WO2006/12135,2006,A1 .Location in patent: Page/Page column 49-51.
[2]Patent: US2006/293379,2006,A1 .Location in patent: Page/Page column 63.

32
[ 738570-45-1 ]
[ 156866-52-3 ]
tert-butyl 4-[4-(oxazol-5-yl)phenylhydrazonomethyl]benzylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;Heating / reflux;	Example 60 tert-Butyl 4-[4-(oxazol-5-yl)phenylhydrazonomethyl]benzylcarbamate tert-Butyl 4-formylbenzylcarbamate (1.35 g) was added to an ethanol solution (30 ml) of 4-(oxazol-5-yl)phenylhydrazine (920 mg), followed by heating overnight under reflux. The solvent was evaporated and the thus obtained residue was washed with diethyl ether to obtain the title compound (1.50 g) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) delta: 1.47 (9H, s), 4.32 (2H, br s), 4.85 (1H, br s), 7.16 (2H, d, J=8.5 Hz), 7.21 (1H, s), 7.30 (2H, d, J=8.1 Hz), 7.57 (2H, d, J=8.5 Hz), 7.61 (2H, d, J=8.1 Hz), 7.71 (1H, s), 7.75 (1H, s), 7.86 (1H, s). ESI-MS m/z: 393 (M+H)+.

References: [1]Patent: EP1612204,2006,A1 .Location in patent: Page/Page column 112.

33
[ 133091-81-3 ]
[ 156866-52-3 ]
[ 405058-77-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium borohydrid; In methanol;	Preparation of {4-[(5,6,7,8-Tetrahydro-quinolin-7-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl ester: Using general procedure B: Reaction of <strong>[156866-52-3](4-Formyl-benzyl)-carbamic acid tert-butyl ester</strong> (356 mg, 1.51 mmol), 5,6,7,8-Tetrahydro-quinolin-7-ylamine (224 mg, 1.51 mmol) in anhydrous MeOH (5 mL) at room temperature overnight under N2 and 2 min of stirring after addition of sodium borohydride (115 mg, 3.00 mmol), followed by purification of crude material using chromatography on silica gel (2:2:96 CH3OH-NH3 H2O-CH2Cl2) afforded the title compound (556 mg, 100percent) as a white foam.

References: [1]Patent: US2002/147192,2002,A1 .

34
[ 6346-09-4 ]
[ 156866-52-3 ]
C₂₁H₃₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The compound (1.04 g) obtained in Example 23-3 was dissolved in anhydrous methanol (40 ml) and added with 4,4-diethoxy-butylamine (863 mg) and trimethyl orthoformate (1.44 ml). The whole was stirred at room temperature for 3 hours. The solution was added with sodium borohydride (499 mg) and the whole was stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off. The resultant was added with water, subjected to extraction with chloroform, and then dried with magnesium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate). The resultant was dissolved in methanol (25 ml) and water (4.8 ml) and added with acrylonitrile (0.43 ml). The whole was stirred at room temperature for 16.5 hours. After completion of the reaction, the solvent was distilled off. The resultant was subjected to extraction with chloroform and dried with magnesium sulfate. The solvent was distilled off. The resultant was dissolved in THF (12 ml), acetone (12 ml), and 1 mol/l hydrochloric acid (12 ml) and the whole was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The resultant was dissolved in anhydrous methanol (26 ml) and added with piperidine (0.49 ml) and sodium cyanoborohydride (415 mg). After the solution was adjusted to pH 5 with acetic acid, the whole was stirred at room temperature for 3 days. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subj ected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.13 g) as a colorless oily substance. MS(FAB,Pos.):m/z=429[M+H]+ 1H-NMR(500MHz,CDCl3):delta=1.27-1.50(6H,m),1.47(9H,s),1.55-1.60(4H,m),2.25(2H,t,J=7.3Hz),2.34(4H,br),2.40(2H,t,J=7.0Hz),2.49(2H,t,J=6.9Hz),2.77(2H,t,J=7.0Hz),3.59(2H,s),4.31(2H,d,J=5.5Hz),7.23(2H,d,J=7.9Hz),7.29(2H,d,J=8.2Hz).

References: [1]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 85.

35
[ 675136-88-6 ]
[ 156866-52-3 ]
[ 675138-34-8 ]

Yield	Reaction Conditions	Operation in experiment
		The compound (225.3 mg) obtained in Example 103-3 was dissolved in methanol (6.76 ml). Then, the solution was added with the compound (165.0 mg) obtained in Example 1-2 and trimethyl orthoformate (304.8 mg), followed by stirring at room temperature for 18 hours. Sodium borohydride (108.7 mg) was added to the solution under ice-cooling, followed by stirring at room temperature for 0.5 hours. The reaction solution was added with water and subjected to separation/extraction with chloroform. Then, the extract was washed with saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (297.6 mg) as a colorless oily substance.
		The compound (9.25 g) obtained in Example 1-2 was dissolved in anhydrous methanol (200 ml) and then added with trimethyl orthoformate (8.81 ml) and the compound (12.6 g) obtained in Example 23-3. The whole was stirred at room temperature for 1.5 hours under a nitrogen atmosphere. Then, sodium borohydride (2.03 g) was added thereto in an ice bath and the whole was stirred at room temperature for 2 hours. After completion of the reaction, distilled water was added thereto and the whole was stirred for awhile. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (19.3 g) as a colorless oily substance.

References: [1]Patent: EP1550657,2005,A1 .Location in patent: Page/Page column 99.
[2]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 48.

Historical Records

Technical Information

• Acyl Group Substitution • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Ester Cleavage • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 156866-52-3 ]

Aryls

A215531 [108468-00-4]

1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene

Similarity: 0.91

A106255 [117445-22-4]

3-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Similarity: 0.90

A178848 [33233-67-9]

4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Similarity: 0.90

A135173 [71420-95-6]

3-[(Boc-amino)methyl]phenylacetic Acid

Similarity: 0.86

A153751 [174799-52-1]

tert-Butyl (2-(benzylamino)ethyl)carbamate

Similarity: 0.86

Aldehydes

A214232 [135865-78-0]

Boc-(S)-3-Amino-3-phenylpropanal

Similarity: 0.82

A164452 [144072-30-0]

(4-Formyl-phenyl)-carbamicacidtert-butylester

Similarity: 0.81

A226436 [176980-36-2]

tert-Butyl (3-formylphenyl)carbamate

Similarity: 0.81

A323282 [65564-05-8]

Benzyl 3-oxopropylcarbamate

Similarity: 0.75

A553853 [174855-57-3]

1-Boc-4-(2-Formylphenyl)piperazine

Similarity: 0.74

Amides

A215531 [108468-00-4]

1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene

Similarity: 0.91

A106255 [117445-22-4]

3-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Similarity: 0.90

A178848 [33233-67-9]

4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Similarity: 0.90

A135173 [71420-95-6]

3-[(Boc-amino)methyl]phenylacetic Acid

Similarity: 0.86

A153751 [174799-52-1]

tert-Butyl (2-(benzylamino)ethyl)carbamate

Similarity: 0.86

Amines

A215531 [108468-00-4]

1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene

Similarity: 0.91

A106255 [117445-22-4]

3-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Similarity: 0.90

A178848 [33233-67-9]

4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Similarity: 0.90

A135173 [71420-95-6]

3-[(Boc-amino)methyl]phenylacetic Acid

Similarity: 0.86

A153751 [174799-52-1]

tert-Butyl (2-(benzylamino)ethyl)carbamate

Similarity: 0.86

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

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CAS No.: 156866-52-3

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CAS No.: 156866-52-3

Alternative Products

Product Details of [ 156866-52-3 ]

Safety of [ 156866-52-3 ]

Computational Chemistry of [ 156866-52-3 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 156866-52-3 ]

[ 156866-52-3 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 156866-52-3 ]

Aryls

Aldehydes

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

{[proInfo.proName]}

CAS No.: 156866-52-3

{[proInfo.proName]}

CAS No.: 156866-52-3

Alternative Products

Product Details of [ 156866-52-3 ]

Safety of [ 156866-52-3 ]

Computational Chemistry of [ 156866-52-3 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 156866-52-3 ]

[ 156866-52-3 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 156866-52-3 ]

Aryls

Aldehydes

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 156866-52-3 ]