[ CAS No. 86-86-2 ]

Name: 86-86-2|1-Naphthaleneacetamide|97%
Brand: Ambeed
SKU: A298928
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Quality Control of [ 86-86-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 86-86-2 ]

Product Details of [ 86-86-2 ]

CAS No. :	86-86-2	MDL No. :	MFCD00004047
Formula :	C₁₂H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XFNJVKMNNVCYEK-UHFFFAOYSA-N
M.W :	185.22	Pubchem ID :	6861
Synonyms :

Calculated chemistry of [ 86-86-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.08
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.63
TPSA :	43.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	1.59
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	2.24
Log Po/w (SILICOS-IT) :	2.45
Consensus Log Po/w :	1.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.39
Solubility :	0.76 mg/ml ; 0.00411 mol/l
Class :	Soluble
Log S (Ali) :	-2.11
Solubility :	1.45 mg/ml ; 0.00783 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.07
Solubility :	0.0158 mg/ml ; 0.0000855 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.02

Safety of [ 86-86-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 86-86-2 ]

* 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.

Upstream synthesis route of [ 86-86-2 ]
Downstream synthetic route of [ 86-86-2 ]

[ 86-86-2 ] Synthesis Path-Upstream 1~7

1
[ 5121-00-6 ]
[ 86-86-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With ammonium hydroxide In tetrahydrofuran at 0 - 20℃; for 0.166667 h;	1-naphthaleneacetic acid (93.5 mg, 0.50 mmol) was added to methylene chloride (0.8 mL)And a catalytic amount of DMF were added and while stirring,Further oxalyl chloride (135.6 mg, 1.00 mmol, 2.00 eq.) Was added dropwise,Followed by stirring at room temperature for 15 minutes. After concentrating the resulting solution under vacuum,Was dissolved in tetrahydrofuran (0.8 mL).Ammonia water (28percent, 450.4 mg, 7.50 mmol, 15.0 eq.) At 0 ° C. was added to the solution,It was then stirred at room temperature for 10 minutes. After concentrating the resulting solution under vacuum,Silica gel column chromatography (chloroform / methanol(10/1, Rf = 0.50)) to obtain the target substance (Y-015) as a white solid (yield 72percent).

Reference： [1] Patent: JP2015/89885, 2015, A, . Location in patent: Paragraph 0146; 0147; 0162-0164
[2] Chimica e l'Industria (Milan, Italy), 1955, vol. 37, p. 857,860
[3] Bulletin de la Societe Chimique de France, 1965, p. 861 - 868
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3366 - 3376
[5] Chemistry Letters, 2015, vol. 44, # 5, p. 621 - 623
[6] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 3, p. 287 - 292

2
[ 86-87-3 ]
[ 86-86-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: With thionyl chloride In dichloromethane at 0℃; for 2 h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;	To a solution of 2—(naphthalen-1—yl)acetic acid (1.50 g, 8.01 mmcl, 1.00 equiv.) in dry CH2C12 (10.0 mL, 0.801 H) was added thionyl chloride (6.73 mL, 92.6 rnmol, 11.5 equiv.) at 0 °C, then the reaction was refluxed for 2 h. The solvent was evaporated and the residue wasazeotroped with toluene (2 xlO.0 mL) . To the crude acyl chloride was added THF (30.0 mL) and NHsH2O (30.0 mL) under vigorous stirring at 0 °C. After the reaction mixture was stirred at room temperature for overnight, the solvent was removed. The residue was purified by column chromatography using with EtOAc:hexane (1 :2 (v/v)) to afford thetitle compound as a white solid (1.31 g, 7.07 mmcl, 88percent yield)NMR Spectroscopy: 1H NMR (700 MHz, (CD3)2S0, 25 °C, 5): 8.08 (d, J =8.3 Hz, 1H), 7.92 (d, J = 7.7 Hz, lH), 7.81 (d, J = 7.7 Hz, 1H), 7.56—7.49 (m, 3H), 7.45—7.41 (m, 2H), 6.99 (s, 1H), 3.86 (s, 2H). C NMR(175 MHz, (CD)2SO, 25 °C, 5): 172.1, 133.3, 132.9, 132.0, 128.3,127.8, 126.9, 125.9, 125.5, 125.5, 124.2. The 1H NMR data were in goodagreement with values reported in the literature (Tu, T. et al. 2012)

Reference： [1] Patent: WO2018/132636, 2018, A1, . Location in patent: Page/Page column 66; 67
[2] Chemische Berichte, 1883, vol. 16, p. 639
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2390 - 2394
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 3, p. 287 - 292

3
[ 132-75-2 ]
[ 86-86-2 ]

Reference： [1] Green Chemistry, 2012, vol. 14, # 4, p. 921 - 924
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 548,549[3] Organic Syntheses, 1963, vol. Coll. Vol. IV, p. 760,762
[4] Patent: US2331711, 1942, ,

4
[ 90-15-3 ]
[ 79-07-2 ]
[ 86-86-2 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 7851 - 7861

5
[ 941-98-0 ]
[ 86-86-2 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1910, vol. <2> 81, p. 387

6
[ 26153-26-4 ]
[ 86-86-2 ]

Reference： [1] Chemische Berichte, 1883, vol. 16, p. 639

7
[ 352352-80-8 ]
[ 86-86-2 ]

Reference： [1] Chemische Berichte, 1883, vol. 16, p. 639

[ 86-86-2 ] Synthesis Path-Downstream 1~69

1
[ 941-98-0 ]
[ 86-86-2 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1910,vol. <2> 81,p. 387

2
[ 132-75-2 ]
[ 86-86-2 ]

Reference： [1]Green Chemistry,2012,vol. 14,p. 921 - 924
[2]Journal of Organic Chemistry,1950,vol. 15,p. 548,549
Organic Syntheses,1963,vol. Coll. Vol. IV,p. 760,762
[3]Patent: US2331711,1942,

3
[ 5121-00-6 ]
[ 86-86-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With ammonium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 0.166667h;	1-naphthaleneacetic acid (93.5 mg, 0.50 mmol) was added to methylene chloride (0.8 mL)And a catalytic amount of DMF were added and while stirring,Further oxalyl chloride (135.6 mg, 1.00 mmol, 2.00 eq.) Was added dropwise,Followed by stirring at room temperature for 15 minutes. After concentrating the resulting solution under vacuum,Was dissolved in tetrahydrofuran (0.8 mL).Ammonia water (28%, 450.4 mg, 7.50 mmol, 15.0 eq.) At 0 C. was added to the solution,It was then stirred at room temperature for 10 minutes. After concentrating the resulting solution under vacuum,Silica gel column chromatography (chloroform / methanol(10/1, Rf = 0.50)) to obtain the target substance (Y-015) as a white solid (yield 72%).
	With 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 0 - 20℃;	General procedure: To an over-dried 100 mL three-necked flask, the carboxylic acid (10 mmol), DMF (5 drops) and DCM (30 mL) were added under a N2 atmosphere. Oxalyl chloride (1.0 mL, 12 mmol) was added dropwise at 0 C resulting in vigorous bubbling. The mixture was stirred for 3 h at room temperature, and the solvent was then removed in vacuo. The resulting acid chloride was used immediately without further purification. To a solution of the acid chloride in DCM (30 mL) ,a solution of 1,1,1,3,3,3-hexamethyldisilazane (30 mmol) in DCM (10 mL) was added dropwise at 0 C, and the solution was then allowed to warm to room temperature. After stirring overnight, the reaction system was quenched with 1 M HCl aq. and saturated aqueous NH4Cl (excess amount) and the organic layer was separated. The aqueous layer was extracted with DCM (2x15 mL). The combined organic layers were washed with saturated aqueous NH4Cl (30 mL) and brine (30 mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting crude material was purified by recrystallization from EtOAc and hexane. The resulting product (5 mmol), 8-bromomethylquinoline (6 mmol), Al2O3 (50 mmol), KOH (25 mmol) and dioxane (30 mL) were added to an over-dried 100 mL three-necked flask. The mixture was stirred for 8 h at 60 C and then was filtered through a celite pad. The filtrate was washed with H2O (30 mL) and the organic layer was separated. The aqueous layer was extracted with EtOAc (2x15 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, filtrated and evaporated in vacuo. The resulting crude amide was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 1/1).

Reference： [1]Patent: JP2015/89885,2015,A .Location in patent: Paragraph 0146; 0147; 0162-0164
[2]Chimica e l'Industria (Milan, Italy),1955,vol. 37,p. 857,860
[3]Bulletin de la Societe Chimique de France,1965,p. 861 - 868
[4]Journal of Medicinal Chemistry,2009,vol. 52,p. 3366 - 3376
[5]Chemistry Letters,2015,vol. 44,p. 621 - 623
[6]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 287 - 292

5
[ 86-86-2 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 86-87-3 ]

Reference： [1]Monatshefte fur Chemie,1912,vol. 33,p. 563

6
[ 86-86-2 ]
[ 132-75-2 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 2203 - 2206
[2]Journal of the American Chemical Society,2018,vol. 140,p. 1627 - 1631
[3]Synthesis,1980,p. 657 - 658
[4]Synthesis,1980,p. 657 - 658
[5]Canadian Journal of Chemistry,1956,vol. 34,p. 1662,1666
[6]Organic Letters,2005,vol. 7,p. 5237 - 5239

7
[ 86-86-2 ]
[1]naphthylacetyl-amidosulfuric acid [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1956,vol. 34,p. 1662,1666

8
[ 86-86-2 ]
[ 4735-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; water;	The intermediate 2-(1-naphthyl)ethylamine was prepared as follows. A suspension of 2-(1-napthyl)acetamide (1.85 g) in tetrahydrofuran (30 mL) was treated dropwise with lithium aluminum hydride (20 mL, 1.0M in THF). After gas evolution ceased, the mixture was heated to reflux for 2 hours, cooled to 0 C., treated dropwise with water (2.9 mL) and filtered. The liltrate was evaporated and purified by chromatography, eluding with chloroform:methanol:ammonium hydroxide (gradient, 100:0:0, 9:1:0, 9:1:0.1), to afford the product (0,240 g) as a semisolid; TLC: Rf =0.09, chloroform:methanol (95:5); MS: m/z=172(M+1).

Reference： [1]Bulletin de la Societe Chimique de France,1965,p. 861 - 868
[2]Patent: US5532366,1996,A

9
[ 95-14-7 ]
[ 86-86-2 ]
[ 100-52-7 ]
N-(Benzotriazol-1-yl-phenyl-methyl)-2-naphthalen-1-yl-acetamide [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 381 - 387

10
[ 86-86-2 ]
[ 118-31-0 ]

Reference： [1]Chemistry Letters,1989,p. 463 - 464

11
[ 86-86-2 ]
[ 39110-74-2 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4272 - 4276

12
[ 86-86-2 ]
[ 298-12-4 ]
[ 110599-20-7 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 439 - 450

13
[ 86-86-2 ]
[ 86-53-3 ]

Reference： [1]Synthesis,1994,p. 1127 - 1128

14
[ 28539-02-8 ]
[ 86-86-2 ]
N-Benzotriazol-1-ylmethyl-2-naphthalen-1-yl-acetamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 4002 - 4005

15
[ 18372-22-0 ]
[ 86-86-2 ]
3-(1H-indol-3-yl)-4-naphthalen-1-yl-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1109 - 1112
[2]Journal of Organic Chemistry,2003,vol. 68,p. 8008 - 8014
[3]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3835 - 3839

16
[ 51079-10-8 ]
[ 86-86-2 ]
3-(1H-indol-3-yl)-4-naphthalen-1-yl-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1109 - 1112
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 1271 - 1281

17
[ 86-86-2 ]
[ 151490-40-3 ]
[ 125313-42-0 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1109 - 1112

18
[ 86-86-2 ]
[ 25055-54-3 ]
[ 125313-42-0 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1109 - 1112

19
[ 891143-61-6 ]
[ 86-86-2 ]
N-(2-{(3aS,8aS)-2,2-Dimethyl-7-[2-(2-naphthalen-1-yl-acetylamino)-benzyl]-6,6-dioxo-hexahydro-1,3-dioxa-6λ⁶-thia-5,7-diaza-azulen-5-ylmethyl}-phenyl)-2-naphthalen-1-yl-acetamide [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 4671 - 4675

20
[ 862884-26-2 ]
[ 86-86-2 ]
N-[2-((3aS,8aS)-7-Benzyl-2,2-dimethyl-6,6-dioxo-hexahydro-1,3-dioxa-6λ⁶-thia-5,7-diaza-azulen-5-ylmethyl)-phenyl]-2-naphthalen-1-yl-acetamide [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 4671 - 4675

21
[ 67-56-1 ]
[ 86-86-2 ]
[ 2876-78-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydrogensulfate; at 65℃; for 12h;	General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products

Reference： [1]Arkivoc,2018,vol. 2018,p. 174 - 183
[2]European Journal of Organic Chemistry,2007,p. 1026 - 1030

22
[ 86-86-2 ]
(4S,5S)-3,4,5,6-tetrahydro-2-{2-[2-(2-naphthyl)-acetamido]-benzyl}-7-benzyl-4,5-dihydroxy-1,2,7-thiadiazepine 1,1-dioxide [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 4671 - 4675

23
[ 86-86-2 ]
(4S,5S)-3,4,5,6-tetrahydro-2,7-bis{2-[2-(2-naphthyl)-acetamido]-benzyl}-4,5-dihydroxy-1,2,7-thiadiazepine 1,1-dioxide [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 4671 - 4675

24
[ 86-86-2 ]
N-[3-(2,3-dimethyl-phenylsulfamoyl)-phenyl]-3-(2-naphthalen-1-yl-acetylamino)-propionamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1991 - 2006

25
[ 86-86-2 ]
[ 78634-33-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 381 - 387

26
[ 86-86-2 ]
[ 110599-17-2 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 439 - 450

27
[ 86-86-2 ]
[ 110599-25-2 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 439 - 450

28
[ 26153-26-4 ]
[ 86-86-2 ]

Reference： [1]Chemische Berichte,1883,vol. 16,p. 639

29
[ 352352-80-8 ]
[ 86-86-2 ]

Reference： [1]Chemische Berichte,1883,vol. 16,p. 639

30
[ 634605-31-5 ]
[ 86-86-2 ]
[ 634605-03-1 ]
[ 634605-04-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3h;	3-BUTYNYL P-TOSYLATE Compound 2a (0.90 g, 4.0 MMOL) and 2-METHYLAMINOETHANOL (0.30 g, 4.0 mmol) were dissolved in DMF (2 mL) and sodium bicarbonate (0.34 g, 4.0 MMOL) was added. The mixture was heated to 75 C under argon for 2 h then cooled to rt and partitioned between DCM (30 mL) and saturated sodium bicarbonate (15 mL). The organic layer was washed once with sodium bicarbonate (15 mL), once with brine (10 mL), then dried (NA2SO4) and evaporated in vacuo to give Compound 2b as a colorless oil (0.98 g). Compound 2b was added to Compound 1b (0.43 g, 2.1 MMOL) followed by triphenyl phosphine (0.73 g, 2.8 MMOL) in THF (15 mL) and DIETHYLAZODICARBOXYLATE (0.49 g, 2.8 MMOL) and the mixture was stirred at ambient temperature for 1 h. The product was evaporated in vacuo to an oil, which was purified via flash column chromatography (ethyl acetate) to give Compound 2c (0.37 g, 56%) as a tan solid. ES-MS m/z 313 (MH+). A portion of the indole Compound 2c (34 mg, 0.11 MMOL) and 1-naphthalene acetamide (Compound 2d, 18 mg, 0.11 MMOL) in THF (1 mL) were treated with 1 M potassium t-butoxide in THF (0.33 mL, 0.33 MMOL) while being cooled in an ice bath. The mixture was stirred at ambient temperature for 3 h, then treated with 12 N HCI (0.15 mL), stirred for 10 min and evaporated in vacuo to give an oil. The oil was partitioned between chloroform and saturated sodium bicarbonate. The organic layer was washed again with saturated sodium bicarbonate, once with brine, then dried (NA2SO4) and evaporated in vacuo to give a mixture of Compound 17 and Compound 18 (50 mg) as an orange oil. The material was purified by preparative TLC to separate Compound 17 and Compound 18. Compound 17 : H NMR (CDCI3) 5 1.81 (s, 3 H), 2.31 (s, 3H), 2.81 (m, 2H), 3.30 (BD S, 2H), 4.22 (m, 2H), 6.18 (d, J=8. 0HZ, 1H), 6.52 (m, 1 H), 7.0 (m, 1 H), 7.15-8. 0 (m, 8H), 8.07 (s, 1 H) ; ES-MS M/Z 448 (MH+). Compound 18: 1H NMR (CDCI3) 61. 97 (m, 1 H), 2.24 (m, 2H), 2.29 (s, 3H), 2.61 (t, J = 7.3 Hz, 2H), 2.77 (m, 2H), 4.19 (m, 2H), 6.18 (d, J = 8.2 Hz, 1H), 6.51 (m, 1 H), 7.0 (m, 1 H), 7.20-7. 93 (m, 8H), 8.04 (s, 1 H) ; ES-MS M/Z 448 (MH+).

Reference： [1]Patent: WO2003/103663,2003,A2 .Location in patent: Page 56, 57

31
[ 436160-97-3 ]
[ 86-86-2 ]
3-(1-naphthalenyl)-4-[1-(5-pyrimidinyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 0.75h;	The methyl ester Compound 6d (0.2 g, 0.71 MMOL) and amide Compound 8a (94 mg, 0.51 MMOL) were combined in dry THF (5 mL) under argon and cooled in an ice bath as 1 M potassium t-butoxide in THF (2.5 mL, 2.5 mmol) was added with stirring over a 5 min period. After 40 min, the reaction was quenched in an ice bath while 12 N HCI (2 mL, 24 MMOL) was slowly added. The mixture was stirred for 15 min at rt, made slightly basic by the addition of 3N NAOH and extracted with EtOAc. The organic layers were combined and washed with saturated NAHC03 and brine, then dried (NA2SO4) and evaporated in vacuo to give a crude solid (0.25g). The solid was then purified by flash column chromatography (97: 3: 0.3 ; DCM: MeOH : NH40H) to afford Compound 30 (30 mg, 15%) as a yellow flaky solid. Compound 30 was dissolved in excess dilute HCI, then frozen and LYOPHILIZED to give the hydrochloride SALT. H NMR (CD30D) 8 9.22 (s, 1 H), 9.06 (s, 2H), 8.21 (s, 1 H), 7.99 (m, 1H), 7.90 (m, 1H), 7.77 (m, 1H), 7.53 (m, 2H), 7.39 (m, 3H), 7.05 (t, J = 7. 8 HZ, 1 H), 6.53 (t, J=7. 9HZ, 1H), 6.31 (d, J = 8.3 Hz, 1H). ES-MS m/z 417 (MH).

Reference： [1]Patent: WO2003/103663,2003,A2 .Location in patent: Page 67, 68

32
[ 86-86-2 ]
9-benzyl-8-hydroxy-2-(1-naphthylmethyl)adenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		Example 52 9-benzyl-8-hydroxy-2-(1-naphthylmethyl)adenine The desired compound was prepared using 2-(naphthalene-1-yl) acetamide by repeating the procedure of Example 22 (Yield: 22%). 1 H-NMR(DMSO-d6) delta ppm: 3.89 (2H, s), 5.42 (2H, s), 6.39 (2H, s), 7.18-8.05 (12H, m), 10.15 (1H, s). TOF-MS: 382(M+1).

Reference： [1]Patent: US6028076,2000,A

33
[ 86-87-3 ]
isopropanolic HCl [ No CAS ]
aqueous H₂ SO₄ [ No CAS ]
[ 86-86-2 ]
[ 34405-42-0 ]
[ 73867-16-0 ]
2,3,4,5-tetrahydro-3,4,4-trimethyl-5-phenyl-1H-naphth[1,2-d]azepine [ No CAS ]
[ 73867-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; BH3; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In tetrahydrofuran; di-isopropyl ether; water; isopropyl alcohol;	EXAMPLE 7 2,3,4,5-Tetrahydro-3,4,4-trimethyl-5-phenyl-1H-naphth[1,2-d]azepine A solution of 74.5 g. (0.4 mole) of 1-naphthyl acetic acid, 111.0 g. (0.45 mole) of EEDQ and 66.0 g. (0.4 mole) of alpha-(1-amino-1-methylethyl)benzenemethanol in 1 l. tetrahydrofuran is stirred and heated for 2 hours at 65 C. and then allowed to stand for 20 hours at room temperature. THF is evaporated in vacuo, and the residue is taken up with ice and 10% aqueous H2 SO4 solution to pH 2. The resulting amide is extracted twice with 750 ml. ethyl acetate. The combined organic extracts are washed with 500 ml. dilute NaHCO3, dried (Na2 SO4) and evaporated to dryness in vacuo. The oil is dissolved in 1 l. hot isopropyl ether and on standing at 25 C. gives 101.0 g. (77% yield) of N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)-1-naphthaleneacetamide as an off-white crystalline solid of analytical purity, m.p. 106-107 C. To a solution of 41 g. (0.12 mole) of the above naphthaleneacetamide in 500 ml. dry tetrahydrofuran is added 175 ml. (0.175 mole) of BH3 /THF solution over 30 minutes at 0 C. with stirring. After addition, the reaction is allowed to stir overnight at room temperature. Following overnight stirring, water is added dropwise with caution until effervescence ceases, then 50 ml. more water is added all at once. Aqueous HCl (10%) is added to pH 1.0. The acidic reaction is next heated at 64 C. for 1 hour to remove most tetrahydrofuran and destroy excess BH3, after which the mixture is cooled with ice and basicified to pH 10.0 with NH4 OH. The now basic mixture is extracted twice with 750 ml. ethyl acetate. The combined organic extracts are dried (Na2 SO4) and evaporated to a low volume where scratching induces crystallization of about 30 g. of crude product. The crude product (10.0 g.) is purified by making the hydrochloride from isopropanol and isopropanolic HCl giving 8.5 g. of alpha-(1-methyl-1-[2-(1-naphthalenyl)ethyl]amino}-ethyl)benzenemethanol hydrochloride as a white crystalline solid of analytical purity, m.p. 241-242 C.

Reference： [1]Patent: US4261890,1981,A

34
[ 1024583-82-1 ]
[ 86-86-2 ]
[ 1024584-17-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2390 - 2394

35
[ 86-86-2 ]
[ 411235-57-9 ]
[ 694518-58-6 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6441 - 6444

36
[ 7647-01-0 ]
[ 86-86-2 ]
[ 626604-78-2 ]
[ 626603-95-0 ]

Yield	Reaction Conditions	Operation in experiment
48%		A mixture of Compound 1c (406 mg, 1.08 mmol) and Compound 3a (154 mg, 0.83 mmol) in 6 ML of anhydrous THF was stirred under nitrogen and cooled in an ice bath while treating dropwise with 4.2 ML of 1 N potassium t-butoxide in THF. The mixture was stirred for 30 minutes in an ice bath then at room temperature for another 30 min.The reddish mixture was then cooled down and then 2 ML of concentrated HCl was added dropwise.The mixture was stirred for 5 min and then ethyl acetate (250 ML) and H2O (50 ML) were added.The organic layer was separated and washed with saturated NaHCO3 and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a crude product (0.45 g).The crude product was separated by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, from 98:2:0.2 to 95:5:0.5) to give 203.8 mg (48%) of Compound 3 as a yellow solid. 1H NMR (DMSO-d6) delta 8.23 (s, 1H), 8.05 (d, J=6.1 Hz, 2H), 7.97 (d, J=8.1 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.61-7.53 (m, 2H), 7.45 (t, J=7.4 Hz, 1H), 7.31 (t, J=7.5 Hz, 1H), 6.52 (dd, J=4.7, 8.0 Hz, 1H), 6.31 (d, J=7.1 Hz, 1H), 4.35 (t, J=6.9 Hz, 2H), 3.34 (t, J=6.1 Hz, 2H), 1.88 (m, 2H). ES-MS m/z 398 (MH+). Anal. Calcd for C24H19N3O3: C, 72.54; H, 4.82; N, 10.58. Found: C, 72.29; H, 4.88; N, 10.70.

Reference： [1]Patent: US2004/6095,2004,A1 .Location in patent: Page 19

37
[ 86-86-2 ]
[ 95-92-1 ]
[ 1041478-83-4 ]

Reference： [1]Archiv der Pharmazie,2008,vol. 341,p. 273 - 280

38
[ 95-14-7 ]
[ 86-86-2 ]
[ 630-19-3 ]
[ 861393-77-3 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3366 - 3376

39
[ 86-86-2 ]
[ 120-46-7 ]
[ 1235999-34-4 ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 670 - 672

40
[ 86-86-2 ]
[ 123-54-6 ]
[ 1235999-33-3 ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 670 - 672

41
[ 67-56-1 ]
[ 86-86-2 ]
[ 92277-77-5 ]