[ CAS No. 5586-73-2 ]

Name: 5586-73-2|3,3-Diphenylpropan-1-amine|98%
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Quality Control of [ 5586-73-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5586-73-2 ]

Product Details of [ 5586-73-2 ]

CAS No. :	5586-73-2	MDL No. :	MFCD00008202
Formula :	C₁₅H₁₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KISZTEOELCMZPY-UHFFFAOYSA-N
M.W :	211.30	Pubchem ID :	79698
Synonyms :

Calculated chemistry of [ 5586-73-2 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.2
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.22
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.46
Log Po/w (XLOGP3) :	3.05
Log Po/w (WLOGP) :	3.17
Log Po/w (MLOGP) :	3.6
Log Po/w (SILICOS-IT) :	3.57
Consensus Log Po/w :	3.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.36
Solubility :	0.0917 mg/ml ; 0.000434 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.115 mg/ml ; 0.000546 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.42
Solubility :	0.000803 mg/ml ; 0.0000038 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.45

Safety of [ 5586-73-2 ]

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

Application In Synthesis of [ 5586-73-2 ]

* 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 [ 5586-73-2 ]

[ 5586-73-2 ] Synthesis Path-Downstream 1~38

1
[ 3531-24-6 ]
[ 5586-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic acid; platinum Hydrogenation;
	With sodium hydroxide; ammonia; hydrogen In methanol
	Multi-step reaction with 2 steps 1: amalgamated aluminium 2: platinum; acetic acid; H₂SO₄ / Hydrogenation

Reference： [1]Lettre; Wick [Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 189,196]
[2]Carenini; Carissimi; Gentili; Grumelli; Picciola; Ravenna [Arzneimittel-Forschung/Drug Research, 1976, vol. 26, # 12, p. 2127 - 2136]
[3]Lettre; Wick [Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 189,196]

2
[ 2286-54-6 ]
[ 5586-73-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1957,vol. 603,p. 189,196

3
[ 2286-54-6 ]
[ 5586-73-2 ]
[ 41140-46-9 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 858
[2]Journal of the American Chemical Society,1947,vol. 69,p. 858

4
[ 18592-13-7 ]
[ 5586-73-2 ]
[ 73541-50-1 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 228 - 231

5
[ 5586-73-2 ]
[ 79-04-9 ]
[ 137075-21-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 0℃; for 0.75h;	1 g (4.73 mmol, 1 eq.) of 3,3-diphenylpropylamine and 732 μL (5.21 mmol, 1.1 eq.) of triethylamine are diluted in 30 mL of DCM at 0 C under argon. 300 μL (3.77 mmol, 0.8 eq.) of chloroacetyl chloride are added dropwise. White fumes form then gradually dissipate. The mixture is stirred for 45 min. at 0 C, the solution becomes red. A dilute HCl solution is added then the aqueous phase is extracted with DCM. The organic phase is washed once with water then once with brine, dried over MgSO4, filtered and concentrated. The product is obtained in the form of an oil (m = 1.36 g, yield = 100%).1H NMR(400 MHz, CDCl3): ppm 2.24 (q, 2H, CH2), 3.21 (q, 2H, CH2), 3.82-3.92 (m, 3H, CH+CH2), 6.37-6.50 (m, IH, NH), 7.06-7.25 (m, 1OH, aromatic H). MS: 288.09+ (M+H)+, 329.11+ (M+H+CH3CN)+ <n="158"/>TLC: Rf= 0.73 (eluent: DCM/MeOH 95/5)
	With triethylamine; In tetrahydrofuran; at 0℃; for 2h;	Method D: <n="138"/>Synthesis of 2-CMoro-N-("3.3-diphenyl-propylVacetamide:25 g (0.118 mol, 1 eq) of 3,3-diphenyl-propylamine and 20.7 mL (0.147 mol, 1.25 eq) of triethylamine were diluted in 250 mL of THF at 0 C, under argon. 9.85 mL (0.124 mol, 1.05 eq) of chloroacetyl chloride were added dropwise. White fumes formed then gradually dissipated. The mixture was stirred for 2 h at 0 C, the solution became red and a white precipitate formed. The precipitate was filtered then washed several times with EtOAc. The organic phase was extracted with dilute HCl solution, with water then with brine, dried over MgSO4, filtered and concentrated. The product was obtained as a yellow solid (m = 32 g, yield = 91%).1H NMR (400 MHz, CDCl3): δ 2.24 (q, 2H, CH2), 3.21 (q, 2H, CH2), 3.82-3.92 (m, 3H, CH+CH2), 6.37-6.50 (m, IH, NH), 7.06-7.25 (m, 1OH, aromatic H). MS (ES+): 288.09+ (M+H)+, 329.11+ (M+H+CH3CN)+

Reference： [1]Patent: WO2007/60026,2007,A1 .Location in patent: Page/Page column 48; 155-156
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6299 - 6312
[3]Journal of Medicinal Chemistry,1992,vol. 35,p. 4118 - 4134
[4]Patent: WO2008/6625,2008,A2 .Location in patent: Page/Page column 136-137

6
[ 5586-73-2 ]
[ 122-48-5 ]
[ 6154-79-6 ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 623 - 625

7
[ 558-42-9 ]
[ 5586-73-2 ]
1-(3,3-diphenylpropyl)amino-2-methyl-2-propanol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1998,vol. 33,p. 399 - 420

8
[ 5586-73-2 ]
[ 207557-35-5 ]
1-[(3,3-diphenyl)propylamino]acetyl-2-cyano-(S)-pyrrolidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2774 - 2789

9
[ 89424-83-9 ]
[ 5586-73-2 ]
N-[(3,4-methylenedioxy)benzylidene]-N-(3,3-diphenylpropyl)amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 492 - 499

10
[ 5586-73-2 ]
[ 35310-75-9 ]
[1-(3-Bromo-4-methoxy-phenyl)-eth-(E)-ylidene]-(3,3-diphenyl-propyl)-amine [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2006,vol. 59,p. 445 - 456

11
[ 5586-73-2 ]
[ 35310-75-9 ]
N-(3,3-diphenylpropyl)-1-(3-bromo-4-methoxyphenyl)ethylamine [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2006,vol. 59,p. 445 - 456

12
[ 5586-73-2 ]
[ 110661-91-1 ]
[ 1002566-64-4 ]

Yield	Reaction Conditions	Operation in experiment
52.6%	With potassium carbonate; In acetonitrile;Heating / reflux;	EXAMPLE 67 (R)-l-(3<3-diphenvIpropyI)-3-(4-(4-(methylsuIfonamido)phenyl)thiazol-2-vI)-l-(4-oxo-4-(piperidin-3-ylamino)butvI)urea; Step 1: Tert-butyl 3-bromopropionate 1 (0.5 mL, 3.0 mmol) was dissolved in 100 mL of dry acetonitrile. To this solution was added potassium carbonate (0.415g, 3.0 mmol) and 3,3-diphenylpropylamine 2. The reaction mixture was refluxed overnight. The mixture was then allowed to cool to room temperature and was concentrated in vacuo. The crude residue obtained was dissolved in ethyl acetate (45 mL) and washed with saturated aqueous ammonium chloride solution and then with brine. The organics were dried over magnesium sulfate, filtered and concentrated to obtain the crude product as a clear oil. This product was purified by column chromatography on silica using 89:9:l/DCM:MeOH:ammonium hydroxide as eluent. Fractions containing product were combined and concentrated in vacuo to obtain 3 as a white solid (0.54g, 52.6% yield).

Reference： [1]Patent: WO2008/6625,2008,A2 .Location in patent: Page/Page column 65

13
[ 4530-20-5 ]
[ 5586-73-2 ]
[ 1002567-00-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;	Synthesis of [2-(3.3-Diphenyl-propylamino)-ethyll-carbamic acid tert-butyl ester:15 g of 3,3-diphenyl-propylamine (71.1 mmol, 1 eq) and 13.7 g of N-Boc-Glycine (78.2 mmol, 1.1 eq) were diluted in 100 mL of dry DCM. 10.6 g of HOBt (78.2 mmol, 1.1 eq) and 15 g of EDCHCl (78.2 mmol, 1.1 eq) were added to the solution. The reaction mixture was stirred for 16 h at room temperature, under argon, before addition of water. The aqueous phase was extracted several times with DCM, the organics were washed with <n="125"/>brine, dried over MgSO4, filtered then concentrated. The crude product was purified by flash chromatography over silica gel (DCM/ MeOH: 98/ 2 to 96/ 4) to give 23.6 g of the desired amide intermediate [β^-diphenyl-propylcarbamoyty-methylj-carbamic acid tert- butyl ester (90% yield).12 g of this amide intermediate (32.5 mmol, 1 eq) were solubilized in 100 mL of dry THF, under argon. After cooling the solution to O0C, 71.6 mL Of LiAlH4 (1 M in THF, 71.6 mmol, 2.2 eq) were added dropwise to the solution. The reaction mixture was stirred for 16 h at room temperature, then cooled to 0C before slow addition of water. After stirring for 1 h at room temperature, the mixture was filtered to get rid of aluminium salts and the solid was washed several times with EtOAc. The aqueous phase was extracted several times with EtOAc, then the organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified with flash chromatography over silica gel (DCM/ MeOH: 98/ 2 to 90/ 10) to give 8.6 g of the desired secondary amine [2-(3,3-diphenyl-propylamino)-ethyl]-carbamic acid tert-butyl ester (70% yield).1H NMR (400 MHz, DMSO): δ 7.28 (m, 8H, aromatic H), 7.15 (m, 2H, aromatic H), 6.68 (t, IH, NH), 4.02 (t, IH, CH), 2.93 (q, 2H, CH2), 2.45 (t, 2H, CH2), 2.38 (t, 2H, CH2), 2.11 (q, 2H, CH2), 1.36 (s, 9H, 3xCH3). MS (ES+): 355.2+ (M+H)+

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 14955 - 14958
Angew. Chem.,2019,vol. 131,p. 15097 - 15100,4
[2]Patent: WO2008/6625,2008,A2 .Location in patent: Page/Page column 123-124

14
[ 314033-91-5 ]
[ 5586-73-2 ]
[ 314033-93-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 15h;	4 Synthesis of 2-(2-chloroethoxy) methyl-4-(3-chlorophenyl-5-(3,3-diphenylpropylcarbamoyl)-2-methyl-1,4-dihydropyridine-3-carboxylic acid (2-cyanoethyl) ester: 250 mg (0.560 mmol) of 2-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid 5-(2-cyanoethyl) ester, 110 mg (0.570 mmol) of WSC hydrochloride and 120 mg (0.570 mmol) of 3,3-diphenylpropylamine were stirred at room temperature for 15 hours in 4 ml of dichloromethane. After evaporating dichloromethane under reduced pressure, 0.1 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound. Yield: 280 mg (0.450 mmol) (80%) MS (ESI, m/z) 632 (M+H)+ 1H-NMR (CDCl3): 2.14 (2H, s), 2.67 (2H, t), 3.10 (2H, m), 3.72 (2H, m), 3.83 (2H, m), 4.31 (2H, m), 4.73 (1H, s), 4.82 (2H, s), 5.56 (1H, t), 7.11-7.26 (15H, m).
	With hydrogenchloride; In dichloromethane;	4) Synthesis of 6-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-5-(3,3-diphenylpropylcarbamoyl)-2-methyl- 1,4-dihydropyridine-3-carboxylic acid (2-cyanoethyl) ester: 250 mg (0.560 mmol) of 2-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-6-methyl- 1,4-dihydropyridine-3,5-dicarboxylic acid 5-(2-cyanoethyl) ester, 110 mg (0.570 mmol) of WSC hydrochloride and 120 mg (0.570 mmol) of 3,3-diphenylpropylamine were stirred at room temperature for 15 hours in 4 ml of dichloromethane. After evaporating dichloromethane under reduced pressure, 0.1 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane / ethyl acetate = 1/1) to obtain the title compound. Yield: 280 mg (0.450 mmol) (80%) MS (ESI, m/z) 632 (M+H)+ 1H-NMR (CDCl3): 2.14 (2H, s), 2.67 (2H, t), 3.10 (2H, m), 3.72 (2H, m), 3.83 (2H, m), 4.31 (2H, m), 4.73 (1H, s), 4.82 (2H, s), 5.56 (1H, t), 7.11-7.26 (15H, m).

Reference： [1]Patent: US2004/9991,2004,A1 .Location in patent: Page/Page column 41
[2]Patent: EP1191022,2002,A1 .Location in patent: Page 20
[3]Patent: EP1318147,2003,A1

15
[ 215119-93-0 ]
[ 5586-73-2 ]
4-(3-chlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	2 Synthesis of 4-(3-chlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)-1,4-dihydropyridine-3-dicarboxylic acid 2-cyanoethyl ester: 219 mg (0.610 mmol) of 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid mono (2-cyanoethyl) ester, 138 mg (0.720 mmol) of WSC hydrochloride, 201 mg (0.950 mmol) of 3,3-diphenylpropylamine and 20.0 mg (0.160 mmol) of 4-dimethylaminopyridine were stirred at room temperature overnight in 10 ml of dichloromethane. 2 N hydrochloric acid was added and the reaction mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound. Yield: 280 mg (0.510 mmol) (83%) MS (ESI, m/z) 554 (M+H)+ 1H-NMR (CDCl3): 2.05-2.23 (2H, m), 2.21 (3H, s), 2.32 (3H, s), 2.64 (2H, t), 3.06-3.22 (2H, m), 3.72 (1H, t), 4.20-4.35 (2H, m), 4.73 (1H, s), 5.31 (1H, t), 5.58 91H, s), 7.09-7.30 (14H, m).
83.3%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	1) Synthesis of 2-cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)-1,4-dihydropyridine-3-carboxylate 219 mg (0.61 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 138 mg (0.72 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 201 mg (0.95 mmol) of 3,3-diphenylpropylamine and 20 mg (0.16 mmol) of 4-dimethylaminopyridine were stirred in 10 ml of dichloromethane at room temperature overnight. 2 N hydrochloric acid was added to the reaction mixture. After the extraction with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound. Yield: 280mg (0.51 mmol) (83.3%) MS (ESI, m/z) 554 (M+H)+ 1H-NMR (CDCl3): 2.05-2.23 (2H, m), 2.21 (3H, s), 2.32 (3H, s), 2.64 (2H, t), 3.06-3.22 (2H, m), 3.72 (1H, t), 4.20-4.35 (2H, m), 4.73 (1H, s), 5.31 (1H, t), 5.58 (1H, s), 7.09-7.30 (14H, m)

Reference： [1]Patent: US2004/9991,2004,A1 .Location in patent: Page/Page column 39
[2]Patent: US6350762,2002,B1 .Location in patent: Page column 37

16
[ 5586-73-2 ]
[ 94790-37-1 ]
[ 141595-76-8 ]
[ 248921-61-1 ]

Yield	Reaction Conditions	Operation in experiment
0.63 g (72%)	With N-ethyl-N,N-diisopropylamine; In diethyl ether; N,N-dimethyl-formamide;	EXAMPLE 5 Preparation of (S)-Azepane-1-carboxylic acid [1-(3,3-diphenyl-propylcarbamoyl)-3-methyl-butyl]-amide (S)-2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (0.51 g, 2.0 mmol, Example 1, Step B) was dissolved in dry DMF (5 mL) under nitrogen atmosphere and cooled to 0 C. in an ice-water bath. To this solution were added, in succession, N,N-diisopropylethylamine (0.68 mL, 3.9 mmol) and solid O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.74 g, 2.0 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; 3,3-diphenylpropylamine (0.41 g, 1.9 mmol, Aldrich, Milwaukee, Wis.) was then added. After additional 30 minutes stirring at 0 C., reaction mixture was mixed with 60 mL of diethyl ether; the resulting mixture was successively washed with 5% aqueous HCl solution, brine, saturated aqueous NaHCO3 solution, brine, and was dried over Na2SO4. The solution was concentrated in vacuo, a white solid was obtained. Recrystallization from EtOAc-hexanes afforded 0.63 g (72%) of the pure titled compound as a white solid; mp 144-145 C. APCI-MS m/z 450.3 (MH+).

Reference： [1]Patent: US6458781,2002,B1

17
ethereal HCl [ No CAS ]
[ 5586-73-2 ]
[ 94790-37-1 ]
(S)-4-methyl-2-piperidin-1-yl-pentanoic acid monohydrobromide [ No CAS ]
[ 248921-85-9 ]

Yield	Reaction Conditions	Operation in experiment
0.39 g (59%)	With N-ethyl-N,N-diisopropylamine; In diethyl ether; hexane; ethyl acetate; N,N-dimethyl-formamide;	EXAMPLE 24 Preparation of (S)-4-Methyl-2-piperidin-1-yl-pentanoic acid (3,3-diphenyl-propyl)-amide monohydrochloride (S)-4-Methyl-2-piperidin-1-yl-pentanoic acid monohydrobromide (0.300 g, 1.51 mmol, Example 22, Step A) was dissolved in dry DMF (4 mL) under nitrogen atmosphere and cooled to 0 C. in an ice-water bath. To this solution were added, in succession, N,N-diisopropylethylamine (0.524 mL, 3.01 mmol) and solid O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.571 g, 1.51 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; 3,3-diphenylpropylamine (0.318 g, 1.50 mmol) was then added. After stirring for, sequentially, 10 minutes at 0 C. and 45 minutes at ambient temperature, reaction mixture was mixed with 60 mL of diethyl ether; the resulting mixture was successively washed with saturated aqueous NaHCO3 solution (260 mL), brine (260 mL), and was dried over Na2SO4. The solution was concentrated in vacuo affording an viscous oil. The crude product was further purified by flash chromatography (60% EtOAc in hexane) and treated with ethereal HCl. Subsequent concentration in vacuo and drying under vacuum provided 0.39 g (59%) of the pure titled compound as a white foam: mp 58-65 C. APCI-MS m/z 393.3 (MH+).

Reference： [1]Patent: US6458781,2002,B1

18
ethereal HCl [ No CAS ]
(S)-2-(Cyclohexyl-methyl-amino)-4-methyl-pentanoic acid [ No CAS ]
[ 5586-73-2 ]
[ 94790-37-1 ]
(S)-2-(Cyclohexyl-methyl-amino)-4-methyl-pentanoic acid (3,3-diphenyl-propyl)-amide monohydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.31 g (50%)	With N-ethyl-N,N-diisopropylamine; In diethyl ether; hexane; ethyl acetate; N,N-dimethyl-formamide;	EXAMPLE 25 Preparation of (S)-2-(Cyclohexyl-methyl-amino)-4-methyl-pentanoic acid (3,3-diphenyl-propyl)-amide monohydrochloride (S)-2-(Cyclohexyl-methyl-amino)-4-methyl-pentanoic acid (0.300 g, 1.32 mmol, Example 21, Step A) was dissolved in dry DMF (4 mL) under nitrogen atmosphere and cooled to 0 C. in an ice-water bath. To this solution were added, in succession, N,N-diisopropylethylamine (0.460 mL, 2.63 mmol) and solid O-benzotriazol-1-yl-N,N,N',N '-tetramethyluronium hexafluorophosphate (0.501 g, 1.32 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; 3,3-diphenylpropylamine (0.279 g, 1.32 mmol) was then added. After stirring for, sequentially, 15 minutes at 0 C. and 30 minutes at ambient temperature, reaction mixture was mixed with 60 mL of diethyl ether; the resulting mixture was successively washed with saturated aqueous NaHCO3 solution (260 mL), brine (260 mL), and was dried over Na2SO4. The solution was concentrated in vacuo affording an viscous oil. The crude product was further purified by flash chromatography (40% EtOAc in hexane) and treated with ethereal HCl. Subsequent concentration in vacuo and drying under vacuum provided 0.31 g (50%) of the pure titled compound as a white foam: mp 67-86 C.; APCI-MS m/z 421.4 (MH+).

Reference： [1]Patent: US6458781,2002,B1

19
[ 5561-92-2 ]
[ 5586-73-2 ]
(R,S)-N-1-(2-methoxyphenylpropyl)-3,3-diphenylpropylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.4%	With sodium cyanoborohydride In diethyl ether; ethanol	(R,S)-N-1-(2-methoxyphenylpropyl)-3,3-diphenylpropylamine (Compound 167) (R,S)-N-1-(2-methoxyphenylpropyl)-3,3-diphenylpropylamine (Compound 167) A solution of 2-methoxypropiophenone (0.848 g, 5.17 mmol), 3,3-diphenylpropylamine (1.00 g, 4.70 mmol), and titanium(IV) isopropoxide [Ti(OCH(CH3)2)4; (1.76 mL, 5.88 mmol, 1.25 equiv)] was stirred at room temperature for 6 h. EtOH (2 mL) was then added, followed by sodium cyanoborohydride (0.295 g, 4.70 mmol) in portions over a period of 10 min, and the reaction was then stirred for 18 h. The reaction mixture was then poured into diethyl ether (200 mL) and the resulting suspension was centrifuged to remove the titanium precipitate. The supernatant was collected and the pellet was rinsed with diethyl ether (200 mL). The combined organic washings were evaporated under vacuum to give a crude oil which was chromatographed on silica gel (elution with 4% MeOH--CH2 Cl2) to provide 647 mg (38%) of product. The material was then dissolved in diethyl ether (50 mL), filtered, and excess ethereal HCl was added to precipitate the hydrochloride salt (125 mg, 7.4%) as a white solid; TLC, Rf 0.25 (4% MeOH-CH2 Cl2); GC, tr =11.2 min; MS, m/z 359 (M+).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US6017965, 2000, A

20
[ 75-09-2 ]
[ 5586-73-2 ]
[ 61406-16-4 ]
[ 78-93-3 ]
2-(3,3-diphenyl-propylamino)-1-methyl-1,4,5,6-tetrahydropyrimidine hydroiodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide In methanol; isopropyl alcohol	7 EXAMPLE 7 EXAMPLE 7 The purpose of this example is to demonstrate the preparation of one member of the new class of cyclic guanidines as described by Formula I, 2-(3,3-diphenylpropylamino)-1-methyl-1,4,5,6-tetrahydropyrimidine. A flask containing 1-methyl-2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (6.00 g, 2.2010-2 mole) and 3,3-diphenylpropylamine (4.91 g, 2.3210-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-165° C. for 50 minutes. The resulting yellow glass was dissolved in methanol. The methanol was partially evaporated at reduced pressure and isopropanol was added. The evaporation was continued being stopped periodically for the addition of small portions of isopropanol. A solid formed which was subsequently collected by filtration. This material was dissolved in a two phase mixture of 5 molar aqueous NaOH (100 ml) and CH2 Cl2 (100 ml). After stirring overnight, the CH2 Cl2 layer was separated. The aqueous alkaline layer was extracted with CH2 Cl2 (2). The CH2 Cl2 layers were combined, washed with H2 O (2), washed with saturated aqueous NaCl, and dried over anhydrous Na2 SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a colorless foam which was dissolved in methanol (50 ml). The solution was cooled to 0° C. before being treated with a methanolic solution of HCl. The methanol was partially evaporated at reduced pressure. 2-Butanone was added and the evaporation was continued on the steam bath until the temperature of the solution reached 78°-79° C. After cooling to room temperature, the solution deposited a solid which was collected by filtration. The product was recrystallized from methanol/2-butanone affording 2-(3,3-diphenyl-propylamino)-1-methyl-1,4,5,6-tetrahydropyrimidine hydroiodide as a colorless solid: 3.44 g (45%), m.p. 178°-180° C. Anal. Calcd. for C20 H25 N3.HCl: C, 69.85; H, 7.62; N, 12.22. Found: C, 69.63; H, 7.68; N, 12.19.

Reference： [1]Current Patent Assignee: MERERU PHARM; SANOFI - US5106845, 1992, A

21
[ 5586-73-2 ]
[ 3027-13-2 ]
[ 59067-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In diethyl ether; ethanol; water;	The mixture of 100 g of m-methoxyphenylacetone, 129 g of 3,3-diphenylpropylamine and 500 ml of anhydrous ethanol is refluxed for 2 hours, cooled to 20 and the solution of 95 g of sodium borohydride in 300 ml of water is added dropwise while stirring at room temperature. After stirring overnight the mixture is poured into water, extracted with methylene chloride, the extract dried and evaporated. The residue is taken up in diethyl ether, the solution acidified with isopropanolic hydrogen chloride and the precipitate collected, to yield the 1-(3-methoxyphenyl)-2-(3,3-diphenylpropylamino)-propane hydrochloride melting at 95-98.

Reference： [1]Patent: US4329367,1982,A

22
[ 5006-66-6 ]
[ 5586-73-2 ]
[ 875471-37-7 ]

Yield	Reaction Conditions	Operation in experiment
26.3%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	1.A Step A: N-(3.3-diphenyl-propylV6-hvdroxy-nicotinamide.To a solution of 6-hydroxy amino-nicotinic acid (0.065 g, 0.473 mmol) in ν,ν,dimethylforrnamide (4 mL) is added 3,3-diphenyl-propylamine (0.100 g, 0.473 mmol) followed by the addition of 1-hydroxybenzotriazole (0.127 g, 0.946 mmol), l-ethyl-3-(3- dimethylaminopropyl)-carbodiimide hydrochloride (0.180 g, 0.946 mmol) and EPO di.^α]p<0ιtyyiethyllaii6tt).2>47 mL, 1.419 mmol). The reaction is stirred overnight. The mixture is diluted with water and the product is extracted using dichloromethane. The organic extract is passed through a cartridge containing silica gel and magnesium sulfate. The resulting compound is purified by flash chromatography using methanol/dichloromethane (2:98 through 10:90) as the eluent and evaporated in vacuo to provide the desired compound (0.041 g, 26.3 %).

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2007/44491, 2007, A1 Location in patent: Page/Page column 21-22

23
[ 5586-73-2 ]
[ 88089-94-5 ]
[ 1030266-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 4 - 8h;	To a solution of ester 2 (0.91 g, 3.32 mmol, 1.0 equiv) in 10 mL of dichloromethane was added dropwise 3,3-diphenyl-propylamine (1.40 g, 6.64 mmol, 2.0 equiv). The mixture was stirred at room temperature for 8 hours. After the amine salt thus obtained was removed by filtration, the solvent in the filtered solution was removed under vacuum to give crude 4-[(3,3-diphenyl-propylamino)-methyl]-3-nitro-benzoic acid methyl ester 3. The crude product was purified by column chromatography using hexane-ethyl acetate (25%) to give ester 3 as a light brown oil.

Reference： [1]Patent: US2008/132501,2008,A1 .Location in patent: Page/Page column 9-10

24
[ 5586-73-2 ]
[ 25271-35-6 ]
[ 1041193-10-5 ]

Yield	Reaction Conditions	Operation in experiment
		In a 3 necked flask under an atmosphere, of nitrogen, <strong>[25271-35-6]N-methylpiperidine-2-carboxylic acid hydrochloride</strong> (1.79g, 10.0 mmol), HOBt (1.35g, 10 mmol). EDC hydrochloride (1.92g, 10 mmol) and TEA (3.0Og, 30mmol) were dissolved in CH2Cl2 (100 mL, dry) at 0C. After 30 min, diphenylpropylamine (2.11g, 10 mmol) was added. After 1 more hour stirring at 0C, the mixture was allowed to stir at rt overnight. When TLC showed consumption of (nearly) all starting materials, the reaction mixture was quenched with water (150 mL). The layers were separated and the organic layer was washed with NaHCO3 (50 mL, sat.), dried (MgSO4), filtered and concentrated in vacuo to yield a yellow/orange oil (4.12g). This crude oil was purifierd by chromatography (Silica, CH2C12/CH3OH, gradient 0-3%) to yield a colorless oil (2.6g, 7.7 mmol).

Reference： [1]Patent: WO2008/87421,2008,A2 .Location in patent: Page/Page column 15

25
[ 5586-73-2 ]
[ 67-64-1 ]
[ 159149-65-2 ]

Yield	Reaction Conditions	Operation in experiment
90.9%		To a solution of 3,3-diphenylpropan-l-amine 1 (4.22 g, 20.0 mmol) in DCE (100 mL) at room temperature was added acetone (1.19 g, 20.5 mmol, 1.50 mL), acetic acid (1.21 g, 20.1 mmol, 1.15 mL), and NaBH(OAc)3 (5.98 g, 28.2 mmol). The reaction mixture was stirred at room temperature for 5 min, a significant amount of precipitate formed, THF (40 mL) was added, and stirring was continued at room temperature for 3 h. The reaction mixture was quenched with 5 M NaOH, partially concentrated, and diluted with EtOAc. The aqueous phase was extracted with EtOAc (2 x) and the combined organic extracts were washed with brine (1 x), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2 M NH3) in DCM) gave JV- isopropyl-3,3-diphenylpropan-l-amine 2 (4.60 g, 90.9% yield) as a colorless oil. Mass spectrum: calculated for Ci8H23N 253.2; found 254.2 (M+ + 1).

Reference： [1]Patent: WO2009/9122,2009,A2 .Location in patent: Page/Page column 51

26
[ 207399-07-3 ]
[ 5586-73-2 ]
C₅₁H₆₀N₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7406 - 7408

27
[ 824426-35-9 ]
[ 5586-73-2 ]
KMJ-378 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h;	General procedure: A mixture of acid (10 mmol), amine (12 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (12 mmol) in CH2Cl2 (20 mL) was stirred for 12 h at room temperature. The reaction mixture was filtered off and the filtrate was concentrated. The residue was purified by flash column chromatography on silica gel using EtOAc-hexanes as eluant.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 1310 - 1318

28
[ 89583-07-3 ]
[ 5586-73-2 ]
[ 913686-05-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2451 - 2454

29
[ 5586-73-2 ]
[ 7699-03-8 ]
[ 1061757-69-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 4h;	To a solution of compound 7c (42 mg, 0.17 mmol) in MeOH (1.7 mL) was added NaOH (21 mg, 0.52 mmol) and the reaction mixture was heated to 90 C for 12 h. The solution was cooled to r.t. and concentrated. To the residue, H2O (5 mL) was added and then extracted with Et2O (3 × 10 mL). The aqueous phase was adjusted to pH 1 with aq 1 M HCl and extracted with EtOAc (3 × 10 mL). The combined organic layers were washed with brine, dried (anhyd Na2SO4) and concentrated to give the acid compound, which was used directly in the next step without further purification. In a glass tube, to a solution of the above obtained acid (23 mg, 0.1 mmol), Et3N (50 mg, 0.5 mmol), 3,3-diphenylpropan-1-amine (42 mg, 0.2 mmol) in DMF (1 mL) was added HATU (76 mg, 0.2 mmol) at r.t. and the reaction mixture was stirred for 4 h. The reaction was quenched with aq NaHCO3 and extracted with EtOAc (3 × 10 mL). The combined organic layers were washed with brine, dried (anhyd Na2SO4), and concentrated. The residue was purified by column chromatography over silica gel (CH2Cl2/MeOH 10:1) to give 8 (30 mg, 71%) as a colorless solid; mp 153-155 C. IR (ATR): 3852, 3621, 3537, 3319, 3031, 2923, 2870, 2473, 2297, 2184, 2125, 2068, 1974, 1888, 1739, 1614, 1516, 1444, 1363, 1230, 1085, 1029, 964, 834, 793, 740, 698 cm-1. 1H NMR (600 MHz, CD3OD): δ = 7.30-7.20 (m, 9 H), 7.18-7.16 (m, 4H), 7.13-7.09 (m, 4 H), 6.74 (d, J = 9.0 Hz, 2 H), 4.85 (s, 1 H), 3.87 (t, J =7.8 Hz, 1 H), 3.13 (t, J = 7.2 Hz, 2 H), 2.25-2.22 (m, 2 H). 13C NMR (151 MHz, CD3OD): δ = 173.8, 156.2, 144.4, 140.2, 130.5 (2 C), 129.5 (2 C), 128.4 (2 C), 128.1 (4 C), 128.0 (2 C), 127.4 (4 C), 126.5, 125.8 (2 C), 114.8 (2 C), 57.0, 48.4, 37.9, 34.5. MS (ESI): m/z = 422.2 [M + H]+. HRMS (ESI): m/z [M + H]+ calcd for C29H28NO2+: 422.2115; found: 422.2120.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 6904 - 6907
[2]Synthesis,2018,vol. 50,p. 872 - 880

30
[ 2327-99-3 ]
[ 5586-73-2 ]
[ 390-64-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1-phenylpropadiene; 3-diphenylpropyl amine With tris(dimethylamido)(trityl(6-(tritylamino)pyridin-2-yl)amido)-titanium In toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With sodium cyanoborohydride; zinc(II) chloride In methanol at 25℃; for 20h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Lühning, Lars H.; Brahms, Christian; Nimoth, Jelte P.; Schmidtmann, Marc; Doye, Sven [Zeitschrift fur Anorganische und Allgemeine Chemie, 2015, vol. 641, # 12-13, p. 2071 - 2082]

31
[ 607-68-1 ]
[ 5586-73-2 ]
2-chloro-N-(3,3-diphenylpropyl)quinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In tetrahydrofuran; at 20℃; for 3h;	j00220j A mixture of 2,4-dichloroquinozoline (1.0 g, 5.02 mmol) and 3,3-diphenylpropan-1-amine (1.167 g, 5.5 mmol) and triethylamine (0.84 mL, 6.02 mmol) in THF (20 mL) wasstirred at room temperature for 3 hours. The reaction mixture was filtered and concentrated.The residue was purified by recrystallization from ether to obtain 1.42 g (7 6%) of 2-chloro-N-(3,3-diphenylpropyl)quinazolin-4-amine. Mp 142-144 C. TLC Rf 0.37 (EtOAc-hexane,75:25). ‘H NMR (400 MHz, DMSO-d6) ö 8.73 (t, J= 5.4 Hz, 1H), 8.23 (ddd, J= 8.5, 1.3, 0.7Hz, 1H), 7.78 (dddd, J= 8.3, 7.0, 1.4, 0.5 Hz, 1H), 7.60 (ddd, J= 8.4, 1.2, 0.6 Hz, 1H), 7.52(dddd, J= 8.2, 6.9, 1.3, 0.5 Hz, 1H), 7.41-7.33 (m, 4H), 7.33-7.24 (m, 4H), 7.17 (tdt, J= 6.8,1.7, 0.8 Hz, 2H), 4.10 (t, J= 7.7 Hz, 1H), 3.43 (ddd, J= 9.0, 7.4, 5.5 Hz, 2H), 2.44 (ddd, J=9.1, 7.5, 5.7 Hz, 2H). MS m/z 374 (M + H). Elemental analysis calculated (%) forC23H20N3Cl0.5H2O: C 72.15, H 5.33, N 10.97. Found: C 72.21, H 4.85, N 10.68.

Reference： [1]Patent: WO2016/90296,2016,A1 .Location in patent: Paragraph 00220

32
[ 5586-73-2 ]
[ 1459-15-0 ]
(-)-Fendiline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In acetonitrile; at 100℃; for 48h;	General procedure: According to general procedure IV S-1-phenylethanol (S-1,126 ilL, 125 mg, 1.00 mmol, 1.0 equiv, 99% ee according chiralGC), FPyr (19.7 ilL, 20.4 mg, 0.20 mmol, 20 mol%), MTBE (0.5 mL,2 M) and benzoyl chloride (141 ilL, 170 mg, 1.20 mmol, 1.2 equiv)were combined at 0 C and stirred for 30 mm at 0 C and for 24 hat room temperature. Then the reaction mixture was diluted withMeCN (2.0 mL), K2C03 (320 mg, 2.30 mmol, 2.3 equiv) and 3,3-diphenylpropane-1-amine (283 mg, 1.30 mmol, 1.3 equiv) were added and the resulting reactionsuspension was stirred for 48 h at 100 C. The work up was slightly modified compared to generalprocedure IV: Thus after cooling down to room temperature, the reaction mixture was diluted with Et20 (4 mL) and water (4 mL). Subsequently, the aqueous phase was extracted with CH2CI2 (2 x 3 mL), the combined organic phases were dried over Mg504 and concentrated in vacuo. Chromatographic purification on silica gel (mass of crude material/5i02 1:30) with Et20/NEt3/nPen 25:4:69 of the crudeproduct (459 mg) furnished the piperidine derivative S82q as a pale yellow oil (248 mg, 0.787 mmol,79%). Comparison of the rotatory degree with literature values revealed an enantiopurity of 95% ee.M (C23H25N) = 315.451 g/mol; rf (5i02, Et20) = 0.44 (tailing); HR-MS (Cl, [C23H26N]) calc. 316.2060 u found 316.2039 u, ([C23H25N]j calc. 315.1987 u found 315.1978 u. [aID2 = -46.7 (c = 1.10 g/100 mL,CHCI3), [aID25 = -45.6 (c = 1.10 g/100 mL, CHCI3).Lit-LaID25 = +43.5 (c = 0.98 g/100 mL, CHCI3 for R82q, 95% ee) (see Wakchaure, V. N.; Kaib, p. 5. J.; Leutzsch, M.; List, B. Angew. Chem. mt. Ed. 2015, 54, 11852-11856).

Reference： [1]Patent: WO2016/202894,2016,A1 .Location in patent: Page/Page column 56; 182
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 10145 - 10149
Angew. Chem.,2016,vol. 128,p. 10300 - 10304,5

33
[ 5586-73-2 ]
[ 2286-54-6 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 15802 - 15806
Angew. Chem.,2016,vol. 128,p. 16034 - 16038,5

34
[ 5586-73-2 ]
2-[2,5-bis(4-cyanophenyl)furan-3-yl]acetic acid [ No CAS ]
N-(3,3-diphenylpropyl)-2-[2,5-bis(4-cyanophenyl)furan-3-yl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: A mixture of 12 (0.3 mmol) and PyBOP (0.45 mmol) in THF (20 mL) was stirred for 10 min. Afterwards, the corresponding amine (0.34 mmol) and DIPEA (0.76 mmol) were given to the mixture and stirred overnight at RT. The crude mixture was evaporated, the product was dissolved in EtOAc, washed with Na2CO3 solution, and dried over Na2SO4. After evaporation, the product was purified by column chromatography (eluent: CHCl3/MeOH).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 22 - 40

35
[ 403-45-2 ]
[ 5586-73-2 ]
[ 914385-65-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 48h;	3,3-Diphenylpropan- 1-amine (105.5 mg, 0.5 mmol) was added to a solution of <strong>[403-45-2]6-fluoronicotinic acid</strong> (70.5 mg, 0.5 mmol) in 3 mL N,N-dimethylformamide and followed by the addition of 1- hydroxybenzotriazole (135 mg, 1 mmol), l-[3-(dimethylamino)propyl]-3- ethylcarbodiimde hydrochloride (191 mg, 1 mmol), and diisopropylethylamine (195.5 mg, 1.5 mmol). The reaction was stirred at room temperature for 48 h, the solvent was evaporated under vacuum and the residue was separated by flash LC (silica gel, hexane-ethylacetate 5: 1? 2: 1) to give the desired product, FNDP (121 mg, 72 %). NMR (CHCI3 500 MHz) delta 8.32 (d, J=2.5 Hz, 1H), 8.10-8.06 (m, 1H), 7.27- 7.24 (m, 8H), 7.25 (m, 2H), 7.01-6.98(m, 1H), 5.92 (broad s, 1H), 4.07 (t, J=8Hz, 1H), 3.57 (m, 2H), 2.48 (m, 2H).

Reference： [1]Patent: WO2017/192854,2017,A1 .Location in patent: Page/Page column 36

36
[ 124-38-9 ]
[ 5586-73-2 ]
alkyl acrylate [ No CAS ]
C₁₈H₁₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: To a 25 ml oven-dried Schlenk sealing tube containing a magnetic stir bar were added [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 (6.6 mg, 0.006 mmol), quinuclidine (11.1 mg,0.1 mmol), primary alkyl amine (0.3 mmol), acrylate (0.2 mmol) and 0.5 ml oftoluene and tAmOH mixture (1/3, vol/vol). The reaction tube was sealed, frozenby liquid nitrogen for 10 min, and evacuated under vacuum and backfilled withCO2 (balloon) three times through a three-way stopcock. Liquid nitrogen andthe CO2 balloon were then removed. The reaction tube was sealed and allowedto stand at room temperature for 10 min, at which time the plug of the tube wasslowly opened to release the excess CO2 gas. The tube was then resealed and placedapproximately 3 inches away from a Kessil LED illuminator. The reaction mixturewas stirred and irradiated for 24-48 h. The internal temperature was measured tobe approximately 40 C using an infrared thermometer. The crude mixture wasthen concentrated in vacuo and purified by flash chromatography on silica gelwith a 4g column on a Teledyne ISCO CombiFlash Rf+ Lumen instrument usingthe indicated solvent system.

Reference： [1]Nature Chemistry,2018,vol. 10,p. 1037 - 1041

37
[ 124-38-9 ]
[ 5586-73-2 ]
alkyl methacrylate [ No CAS ]
C₁₉H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With Quinuclidine; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In toluene; at 40℃; under 760.051 Torr;Irradiation;	General procedure: To a 25 ml oven-dried Schlenk sealing tube containing a magnetic stir bar were added [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 (6.6 mg, 0.006 mmol), quinuclidine (11.1 mg,0.1 mmol), primary alkyl amine (0.3 mmol), acrylate (0.2 mmol) and 0.5 ml oftoluene and tAmOH mixture (1/3, vol/vol). The reaction tube was sealed, frozenby liquid nitrogen for 10 min, and evacuated under vacuum and backfilled withCO2 (balloon) three times through a three-way stopcock. Liquid nitrogen andthe CO2 balloon were then removed. The reaction tube was sealed and allowedto stand at room temperature for 10 min, at which time the plug of the tube wasslowly opened to release the excess CO2 gas. The tube was then resealed and placedapproximately 3 inches away from a Kessil LED illuminator. The reaction mixturewas stirred and irradiated for 24-48 h. The internal temperature was measured tobe approximately 40 C using an infrared thermometer. The crude mixture wasthen concentrated in vacuo and purified by flash chromatography on silica gelwith a 4g column on a Teledyne ISCO CombiFlash Rf+ Lumen instrument usingthe indicated solvent system.

Reference： [1]Nature Chemistry,2018,vol. 10,p. 1037 - 1041

38
[ 201230-82-2 ]
[ 5586-73-2 ]
[ 104375-88-4 ]
N-(3,4-dimethoxyphenethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 20 - 60℃; under 2068.65 Torr; for 24h;Inert atmosphere; Autoclave;	General procedure: 5′-O-(4,4′-Dimethoxytrityl)-5-iodo-2′-deoxyuridine (5′-O-DMT-5-IdU) (1a) (1.0 mmol, 656mg), the corresponding amine 2 (2.0 mmol), Pd(OAc)2 (2 mol%), PTABS ligand (4 mol%), Et3N (10 mmol) and N2-purged DMF (10 mL) were added to a 100 mL stainless steel autoclave reaction flask at room temperature. The autoclave was closed and flushed with nitrogen gas and then pressurized with CO gas (40 psi). Caution. Carbon monoxide (CO) is an odorless, colorless and highly toxic gas. The reactions should be carried out in efficient fume hoods fitted with CO detectors. The reaction mixture was stirred with a mechanical stirrer (500 rpm) and heated at 60 C for 24 h. The mixture was then allowed to cool to room temperature and the CO was vented carefully in a fume hood by adding KMnO4 solution. The reaction mass was diluted in cold water and subsequently extracted with EtOAc (3 × 25 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. A slurry was prepared from the residue using silica gel and the product was isolated by column chromatography (60-120 neutralized silica gel; CHCl3/MeOH/Et3N, 97.5:2.0:0.5).

Reference： [1]Synthesis,2019,vol. 51,p. 4239 - 4248

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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. 5586-73-2 ]

Quality Control of [ 5586-73-2 ]

Related Doc. of [ 5586-73-2 ]

Product Details of [ 5586-73-2 ]

Calculated chemistry of [ 5586-73-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5586-73-2 ]

Application In Synthesis of [ 5586-73-2 ]

[ 5586-73-2 ] Synthesis Path-Downstream 1~38

Related Functional Groups of [ 5586-73-2 ]

Aryls

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5586-73-2 ]