[ CAS No. 5122-82-7 ] {[proInfo.proName]}

Name: 5122-82-7|1-(Adamantan-1-yl)-2-bromoethanone|98%
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Quality Control of [ 5122-82-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5122-82-7 ]

Product Details of [ 5122-82-7 ]

CAS No. :	5122-82-7	MDL No. :	MFCD00074740
Formula :	C₁₂H₁₇BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KWCDIRFSULAMOC-UHFFFAOYSA-N
M.W :	257.17	Pubchem ID :	197820
Synonyms :

Calculated chemistry of [ 5122-82-7 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.27
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	3.32
Log Po/w (WLOGP) :	3.17
Log Po/w (MLOGP) :	3.28
Log Po/w (SILICOS-IT) :	3.45
Consensus Log Po/w :	3.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.104 mg/ml ; 0.000404 mol/l
Class :	Soluble
Log S (Ali) :	-3.35
Solubility :	0.114 mg/ml ; 0.000442 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.15
Solubility :	0.18 mg/ml ; 0.0007 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	5.09

Safety of [ 5122-82-7 ]

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

Application In Synthesis of [ 5122-82-7 ]

* 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 [ 5122-82-7 ]
Downstream synthetic route of [ 5122-82-7 ]

[ 5122-82-7 ] Synthesis Path-Upstream 1~2

1
[ 1660-04-4 ]
[ 5122-82-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-Bromosuccinimide In methanol; Petroleum ether at 59.84℃; for 2 h;	1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
78%	at 20℃; for 4 h; Cooling with ice	[359] To an ice- cooling solution of 1-(adamantan-1-yl)ethanone (1.78 g, 10.0 mmol) in THF (30 mL) was added Br2 (1.70 g, 10.7 mmol, dissolved in 5 mL THF). The resultedmixture was stirred at room temperature for 4h, and then the reaction was quenched by addition of saturated sodium thiosulfate solution (20 mL), extracted with dichloromethane (100 mL). The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to afford compound 19.1(2.0 g, yield: 78percent) as a yellow solid.
70%	at 160℃; for 4 h; Sealed tube; Inert atmosphere	General procedure: The reactions were carried out in glass ampoules (20 mL) or in a pressure microreactor of stainless steel (17 mL). The results of parallel experiments were identical. Into the microreactor (ampoule) in an argon atmosphere was charged 0.3 mmol of Fe(acac)₃, 10 mmol of initial adamantane, 10 mmol of CBr₄, and 150 mmol of CH₂Br₂. The reactor was hermetically closed (the ampoule was sealed) and heated while stirring. On the completion of the reaction the reactor (ampoule) was cooled to room temperature, opened, the solvent was distilled off, the residue was crystallized from hexane or ethanol. Yields are given in respect to converted adamantane (adamantine derivatives) (GLC procedure, internal reference decene; correction factor for adamantane 1.09, for bromoadamantane 1.53). The structure of compounds obtained was proved by comparison with known samples and published data.

Reference： [1] Molecules, 2015, vol. 20, # 10, p. 18827 - 18846
[2] Patent: WO2016/131380, 2016, A1, . Location in patent: Paragraph 358; 359
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187[4] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[5] Chemische Berichte, 1960, vol. 93, p. 2054 - 2057
[6] Tetrahedron, 2008, vol. 64, # 22, p. 5191 - 5199

2
[ 186581-53-3 ]
[ 2094-72-6 ]
[ 5122-82-7 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2058 - 2062[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 11, p. 2292 - 2296

[ 5122-82-7 ] Synthesis Path-Downstream 1~62

1
[ 5122-82-7 ]
[ 1660-04-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid for 3h; Irradiation; Inert atmosphere;	Reduction of α-Haloketones 2; General Procedure General procedure: Into a flask charged with the respective α-haloketone 2 (1 mmol) and ethidine (Hantzsch's ester, 1a; 1.2 mmol), was added the solvent as per Tables 2-4 (2.5 mL). The flask was then attached to a balloon filled with N2 and irradiated with 3 W blue LED at a distance of 5 cm. The workup was followed when TLC showed that ethidine or the haloketone was consumed. When AcOH was used as the solvent, the reaction was worked up as follows: the reaction mixture was partitioned between EtOAc (40 mL) and H2O (10 mL), then the organic phase was washed with sat. aq NaHCO3 (3 15 mL) and brine (15 mL), and dried (anhyd Na2SO4). After concentration under reduced pressure, the residue was subjected to flash chromatography for purification eluting with petroleum ether (PE) and CH2Cl2. When aprotic polar solvents were used, the reaction mixture was diluted with EtOAc (40 mL) and the organic layer was washed with H2O (3 15 mL) and brine (15 mL), and dried (anhyd Na2SO4). When volatile solvents were used, the mixture was concentrated under reduced pressure and the residue was subjected to flash chromatography for purification.
	With water; lithium diisopropyl amide 1.) THF/ether, -78 deg C, 10 min, 2.) THF/ether, room temperature; Yield given. Multistep reaction;

Reference： [1]Lu, Zheng; Yang, Yong-Qing [Synthesis, 2019, vol. 51, # 2, p. 508 - 515]
[2]Lion, Claude; Dubois, Jacques-Emile; Lebbar, Khadija [Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 2, p. 119 - 126]

2
[ 5122-82-7 ]
[ 50-06-6 ]
[ 124558-99-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; for 7h;

Reference： [1]Hedayatullah, Mir; Roger, Annie [Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1093 - 1096]

3
[ 5122-82-7 ]
[ 1123-54-2 ]
[ 124558-97-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; for 7h;

Reference： [1]Hedayatullah, Mir; Roger, Annie [Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1093 - 1096]

4
[ 1660-04-4 ]
[ 5122-82-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-Bromosuccinimide In methanol; Petroleum ether at 59.84℃; for 2h;	3.1. Synthesis 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
78%	With bromine at 20℃; for 4h; Cooling with ice;	[358] Intermediate 10: synthesis of 1-(adamantan-1-yl)-2-bromoethanone (19.1) [359] To an ice- cooling solution of 1-(adamantan-1-yl)ethanone (1.78 g, 10.0 mmol) in THF (30 mL) was added Br2 (1.70 g, 10.7 mmol, dissolved in 5 mL THF). The resultedmixture was stirred at room temperature for 4h, and then the reaction was quenched by addition of saturated sodium thiosulfate solution (20 mL), extracted with dichloromethane (100 mL). The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to afford compound 19.1(2.0 g, yield: 78%) as a yellow solid.
70%	With iron(III)-acetylacetonate; carbon tetrabromide at 160℃; for 4h; Sealed tube; Inert atmosphere;	General procedure General procedure: The reactions were carried out in glass ampoules (20 mL) or in a pressure microreactor of stainless steel (17 mL). The results of parallel experiments were identical. Into the microreactor (ampoule) in an argon atmosphere was charged 0.3 mmol of Fe(acac)3, 10 mmol of initial adamantane, 10 mmol of CBr4, and 150 mmol of CH2Br2. The reactor was hermetically closed (the ampoule was sealed) and heated while stirring. On the completion of the reaction the reactor (ampoule) was cooled to room temperature, opened, the solvent was distilled off, the residue was crystallized from hexane or ethanol. Yields are given in respect to converted adamantane (adamantine derivatives) (GLC procedure, internal reference decene; correction factor for adamantane 1.09, for bromoadamantane 1.53). The structure of compounds obtained was proved by comparison with known samples and published data.

	With aluminum tri-bromide; bromine
	With N-Bromosuccinimide; toluene-4-sulfonic acid at 80℃; for 0.166667h;
	With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 90℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Current Patent Assignee: SHENZHEN LANGRUN INVESTMENT CO., LTD. - WO2016/131380, 2016, A1 Location in patent: Paragraph 358; 359
[3]Khusnutdinov; Shchadneva; Khisamova [Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187][Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199]
[4]Stetter,H.; Rauscher,E. [Chemische Berichte, 1960, vol. 93, p. 2054 - 2057]
[5]Pravst, Igor; Zupan, Marko; Stavber, Stojan [Tetrahedron, 2008, vol. 64, # 22, p. 5191 - 5199]
[6]Kang, Lei; Wang, Fang; Zhang, Jinlong; Yang, Huameng; Xia, Chungu; Qian, Jinlong; Jiang, Gaoxi [Organic Letters, 2021, vol. 23, # 5, p. 1669 - 1674]

5
[ 156-81-0 ]
[ 5122-82-7 ]
2-(1-adamantyl)-7-aminoimidazo[1,2-a]pyrimidine hydrobromide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2000,vol. 74,p. 1707 - 1712

6
[ 4214-74-8 ]
[ 5122-82-7 ]
2-(1-adamantyl)-6,8-dichloroimidazo[1,2-a]pyridine hydrobromide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2000,vol. 74,p. 1707 - 1712

7
[ 5122-82-7 ]
[ 3977-29-5 ]
2-(1-adamantyl)-5-methyl-7-hydroxyimidazo[1,2-a]pyrimidine hydrobromide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2000,vol. 74,p. 1707 - 1712

8
[ 7357-70-2 ]
[ 5122-82-7 ]
[ 497933-44-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	In ethanol for 0.166667h; Heating;

Reference： [1]Volovenko; Resnyanskaya; Tverdokhlebov [Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 3, p. 324 - 330]

9
[ 2690-08-6 ]
[ 5122-82-7 ]
[ 761458-86-0 ]

Yield	Reaction Conditions	Operation in experiment
	With silver tetrafluoroborate In acetonitrile	S.10 Synthesis of Compound (I-13) Synthesis Example 10 Synthesis of Compound (I-13) In 100 ml of acetonitrile were dissolved 5.0 g of 1-adamantyl bromomethyl ketone and 7.5 g of octyl sulfide, and 4.5 g of silver tetrafluoroborate was added thereto, followed by refluxing for 3 hours. The reaction mixture was filtered, and the filtrate was concentrated. The resulting oily substance was washed with diisopropyl ether to give 9.5 g of 2-(1-adamantyl)-2-oxoethyldioctylsulfonium tetrafluoroborate.

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US7094515, 2006, B2

10
[ 5122-82-7 ]
[ 62-50-0 ]
C₁₃H₁₈O₃S [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 8587 - 8589

11
[ 5122-82-7 ]
[ 78818-15-2 ]
[ 291751-24-1 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 4-Benzyloxycarbonyl-[1-(2-oxo-2-(adamant-1-yl))ethyl]piperazin-2-one To a round bottomed flask were added <strong>[78818-15-2]4-benzyloxycarbonylpiperazin-2-one</strong> (234.26 mg, 1.0 mmol) along with N,N-dimethylforamide (5.0 ml), and sodium hydride (73.0 mg (60%), 1.0 mmol). After the evolution of hydrogen had ceased the reaction was allowed to stir for an additional 30 minutes. To this was added 1 adamantyl bromomethyl ketone (257.18 mg, 1.0 mmol). The reaction stirred at Rt. for 18hrs. The reaction was poured into water (25 ml) and extracted with ethylacetate (2*25 ml). The ethylacetate layer was washed with brine and dried (MgSO4). Solvent removal yielded 4-benzyloxycarbonyl-[1-(2-oxo-2-(adamant-1-yl)ethyl]piperazin-2-one. 400 Mhz H1 NMR (CDCl3): 1.68-1.91(m,12H), 2.06 (br s,3H), 3.32(t,2H), 3.77(t,2H), 4.20(s,2H), 4.34(s,2H), 5.16(s,2H), 7.36(m,5H). The material was used with out further purification.

Reference： [1]Patent: US2002/72081,2002,A1

12
[ 13382-43-9 ]
[ 5122-82-7 ]
[ 911055-37-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate In acetonitrile at 20 - 60℃; for 24h;	l-Adamantan-l-yl-2-(2-methyl-benzothiazol-5-ylamino)-ethanone (XDS03133,STX1487); EPO To a solution of adamantan-1-yl bromomethyl ketone (129 nig, 0.50 mmol) and 2- methylbenzo[d]thiazol-5-amine (164 mg, 1.0 mmol) in acetonitrile (10 mL) was added potassium carbonate (150 mg). The mixture was stirred at ambient temperature for 18 h, then at 60 0C for 6h, partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give the crude product. Purification with flash column (DCM-ethyl acetate; gradient elution) yielded the title compound as off-white solid (90 mg, 53%). TLC single spot at Rf 0.66 (10% EtOAc/DCM); 1HNMR (270 MHz, CDCl3) δ 1.69 (6H5 m, 3 x CH2), 1.84 (6H5 d, J = 2.7 Hz5 3 x CH2), 2.02 (3H5 broad, 3 x CH), 2.71 (3H, s, CH3), 4.06 (2H5 S5 CH2), 4.75 (IH, broad, NH), 6.68 (IH5 dd, J= 8.6, 2.4 Hz, ArH)5 7.03 (IH5 d, J= 2.2 Hz, AxH) and 7.48 (IH5 d, J = 8.8 Hz5 ArH); LC/MS (APCI) m/z 341 (M+H-H); HPLC tr = 3.53 min (>96%) in 20% water-acetonitrile.
185 mg	With potassium carbonate at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: IPSEN SA - WO2006/100502, 2006, A1 Location in patent: Page/Page column 74-75
[2]Location in patent: experimental part Su, Xiangdong; Pradaux-Caggiano, Fabienne; Thomas, Mark P.; Szeto, Michelle W. Y.; Halem, Heather A.; Culler, Michael D.; Vicker, Nigel; Potter, Barry V. L. [ChemMedChem, 2010, vol. 5, # 7, p. 1026 - 1044]

13
[ 5122-82-7 ]
[ 60-56-0 ]
[ 749843-47-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine; In acetonitrile; at 20℃; for 20h;	l-Adamantan-l-yl-2-(l-methyl-lH-imidazol-2-yIsulfanyI)-ethanone (STX1898, XDS04042); To a solution of adamantan-1-yl bromomethyl ketone (256 mg, 1.0 mmol) in acetonitrile (5 mL) was added 2-mecapto 1-methylimidazole (114 mg, 1.0 mmol), followed by triethylamine (0.5 mL). The mixture was stirred at ambient temperature for 20 h, partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as off-white solid (230 mg, 79%). mp 65-69 C; TLC single spot at Rf. 0.51 (50% EtOAc/hexane); 1H NMR (270 MHz, CDCl3) delta 1.63-1.81 (6H, m, 3 x CH2), 1.82 (6H, d, J= 2.3 Hz, 3 x CH2), 2.03 (3H, broad, 3 x CH), 3.64 (3H, s, CH3), 4,23 (2H, s, CH2), 6.89 (IH, d, J= 1.2 Hz, ArH) and 7.01 (IH,

Reference： [1]ChemMedChem,2011,vol. 6,p. 1439 - 1451
[2]Patent: WO2006/100502,2006,A1 .Location in patent: Page/Page column 127

14
[ 5122-82-7 ]
[ 6258-66-8 ]
[ 64310-53-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In acetonitrile; at 20℃; for 18h;	l-Adamantan-l-yl-2-(4-chIoro-benzylsuIfanyI)-ethanone (XDS03186, STX1621); The solution of adamantan-1-yl bromomethyl ketone (257 mg, 1.0 mmol) and (4-Chloro- phenyl)-methanethiol (159 mg, 1.0 mmol) in acetoniMle/triemylamine (5 mL / 0.5 mL) was stirred at ambient temperature for 18 h, partitioned between ethyl acetate and 5% sodium carbonate solution. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give the crude product. Purification with flash column (hexane-EtOAc; gradient elution) yielded the title compound as white crystalline solid (330 mg, 99%); TLC single spot at Rf. 0.52 (20% EtOAc/DCM); 1H NMR (270 MHz5 CDCl3) delta 1.66-1.78 (6H5 m5 3 x CH2), 1.83 (6H5 d, J= 2.8 Hz, 3 x CH2), 2.06 (3H, broad, 3 x CH), 3.20 (2H, s, CH2), 3.70 (2H, s, CH2) and 7.26 (4H, s, ArH); LC/MS (APCI) m/z 333 (M+-H); HPLC tr = 3.55 min (>98%) in 4% water-acetonitrile.

Reference： [1]ChemMedChem,2010,vol. 5,p. 1026 - 1044
[2]Patent: WO2006/100502,2006,A1 .Location in patent: Page/Page column 79

15
[ 5122-82-7 ]
[ 49543-63-7 ]
[ 911057-29-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In acetonitrile at 20℃;
95%	With triethylamine In acetonitrile at 20℃;	l-Adamantan-l-yl-2-(4-ter/-butyl-benzylsulfanyl)-ethanone (STX2081, FPC01005B); To a solution of 1-adamatyl bromomethyl ketone (100 mg, 0.39 mmol) and 4- tertbutylbenzyl mercaptan (0.726 mL, 0.39 mmol) in CH3CN (2.5 mL) was added triethylarnine (0.108 mL, 0.78 mmol) at room temperature. When the staring materials were consumed, the reaction was partitioned between Ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulphate and concentrated in vacuo. Purification of the residue by flash chromatography (hexane/EtOAc gradient elution) gave the titled compound as white solid (131.6 mg, 95%). TLC single spot at R/ 0.41 (DCM/EtOAc 95:5); 1H NMR (270 MHz, CDCl3): J7.34-7.22 (4H, m), 3.68 (2H, s), 3.17 (2H, s), 2.01 (3H, br s), 1.80 (6H, m), 1.75-1.54 (6H, m), 1.29 (9H, s); LC/MS (APCI) m/z 357.62 (M++..); HPLC tr = 14.86 min (100% purity) in 10% water- acetonitrile.

Reference： [1]Location in patent: experimental part Su, Xiangdong; Pradaux-Caggiano, Fabienne; Thomas, Mark P.; Szeto, Michelle W. Y.; Halem, Heather A.; Culler, Michael D.; Vicker, Nigel; Potter, Barry V. L. [ChemMedChem, 2010, vol. 5, # 7, p. 1026 - 1044]
[2]Current Patent Assignee: IPSEN SA - WO2006/100502, 2006, A1 Location in patent: Page/Page column 141

16
[ 5122-82-7 ]
[ 1126-81-4 ]
[ 880435-57-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In acetonitrile at 20℃;
78%	With triethylamine In acetonitrile at 20℃; for 2h;	N-[4-(2-Adamantan-l-yl-2-oxo-ethylsulfanyI)-phenyl]-acetamide (STX2242,XDS04133); To a solution of adamantan-1-yl bromomethyl ketone (500 mg, 1.94 mmol) in acetonitrile(15 mL) was added N-(4-mercaptophenyl)acetamide (356 mg, 2.13 mmol), followed by triethylamine (1.5 mL). The mixture was stirred at ambient temperature overnight. 2- Chloro-tritylchloride resin (400 mg, 1.6 mmol/g) was added and the mixture was stirred for 2 h, filtered and concentrated in vacuo to give the crude product. Purification with flash column (ethyl acetate/DCM; gradient elution) yielded the title compound as white solid (520 mg, 78 %). TLC single spot at Rf. 0.20 (20% EtOAc/DCM); 1H NMR (270 MHz, CDCl3) δ 1.62-1.75 (6H5 m, 3 x CH2), 1.82 (6H, d, J= 2.8 Hz, 3 x CH2), 2.03 (3H, broad, 3 x CH), 2.16 (3H, s, CH3), 3.86 (2H, s, CH2), 7.21 (IH, broad, NH)5 7.34 (2H, dd, EPO J= 7.0, 2.0 Hz, ArH) and 7.42 (2H, dd, J= 7.0, 2.0 Hz, ArH); LC/MS (APCI) m/z 342 (M+-H); HPLC tr = 5.25 min (>99 %) in 10 % water-acetonitrile.

17
[ 58255-18-8 ]
[ 5122-82-7 ]
1-adamantan-1-yl-2-(methyl-thiophen-2-ylmethyl-amino)-ethanone hydrogenchloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	In acetonitrile; at 20℃; for 4h;	l-Adamantan-l-yI-2-(methyl-thiophen-2-ylmethyl-amino)-ethanone hydrogen chloride (STX1896, XDS04040); To a solution of adamantan-1-yl bromomethyl ketone (256 mg, 1.0 mmol) in acetonitrile (10 mL) was added <strong>[58255-18-8]N-methyl(thiophen-2-yl)methanamine</strong> (128 mg, 1.0 mmol). The mixture was stirred at ambient temperature for 4 h, partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give the crude product. Purification with flash column (DCM- ethyl acetate; gradient elution) yielded the free base of title compound, which was treated with HCl ether solution to give a white solid (65 mg, 19%). mp 201-203 0C (HCl salt); TLC single spot at Rf. 0.30 (20% EtOAc/DCM) (free base); 1H NMR (free base) (270 MHz, CDCl3) delta 1.63-2.00 (12H, m, 6 x CH2), 2.00 (3H, broad, 3 x CH), 2.35 (3H, s, CH3), 3.42 (2H, s, CH2), 3.88 (2H, s, CH2), 6.88 (IH, m, ArH), 6.93 (IH, dd, J= 5.0, 3.5 Hz5 ArH) and 7.23 (IH, dd, J= 5.0, 1.3 Hz, ArH); LC/MS (Free base)(APCI) m/z 304 (M++..); HPLC (HCl salt) ^ = 6.39 min (>99 %) in 20% water-acetonitrile.

Reference： [1]Patent: WO2006/100502,2006,A1 .Location in patent: Page/Page column 126

18
[ 7774-74-5 ]
[ 5122-82-7 ]
[ 911057-05-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In acetonitrile;	l-Adamantan-l-yl-2-(thiophen-2-ylsulfanyl)-ethanone (STX1902, XDS04047); To a solution of adamantan-1-yl bromomethyl ketone (256 mg, 1.0 mmol) in acetonitrile (5 mL) was added 2-mercapto thiophene (0.093 mL, 1.0 mmol), followed by triethylamine (0.5 mL). The mixture was stirred at ambient temperature for 20 h, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as off-white solid (250 mg, 86%). mp 69-72 C; TLC single spot at Rf. 0.59 (50% hexane/DCM); 1H NMR (270 MHz, CDCl3) delta 1.67-1.78 (12H, m, 6 x CH2), 2.02 (3H, broad, 3 x CH), 3.84 (2H, s, CH2), 6.94 (IH, dd, J= 5.1, 3.2 Hz, ArH), 7.15 (IH, dd, J= 3.3, 1.5 Hz, ArH) and 7.34 (IH, dd, J= 5.2, 1.5 Hz, ArH); LC/MS (APCI) m/z 293 (M++..); HPLC tr = 3.60 min (>99 %) in 20% water-acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1439 - 1451
[2]Patent: WO2006/100502,2006,A1 .Location in patent: Page/Page column 129

19
[ 6258-63-5 ]
[ 5122-82-7 ]
[ 911057-02-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	With triethylamine In acetonitrile at 20℃;
52%	With triethylamine In acetonitrile at 20℃; for 20h;	l-Adamantan-l-yl-2-(thiophen-2-ylmethylsulfanyl)-ethanone (STX1899, XDS04043); To a solution of adamantan-1-yl bromomethyl ketone (256 mg, 1.0 mmol) in acetonitrile (5 mL) was added 2-thienyl mercaptan (130 mg, 1.0 mmol), followed by triethylamine(0.5 mL). The mixture was stirred at ambient temperature for 20 h, partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over sodium EPO sulphate and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as waxy-like semi solid (160 mg, 52%). TLC single spot at Rf. 0.59 (50% hexane/DCM); 1H NMR (270 MHz, CDCl3) S 1.62-1.81 (12H, m, 6 x CH2), 2.02 (3H, broad, 3 x CH), 3.32 (2H5 s, CH2), 3.95 (2H5 s, CH2), 6.88-6.94 (2H5 m, ArH) and 7.20 (IH5 dd, J= 5.O5 1.3 Hz5 ArH); LC/MS (APCI) m/z 307 (M++..); HPLC tr = 5.14 min (>97 %) in 20% water-acetonitrile.

Reference： [1]Location in patent: experimental part Su, Xiangdong; Vicker, Nigel; Thomas, Mark P.; Pradaux-Caggiano, Fabienne; Halem, Heather; Culler, Michael D.; Potter, Barry V.L. [ChemMedChem, 2011, vol. 6, # 8, p. 1439 - 1451]
[2]Current Patent Assignee: IPSEN SA - WO2006/100502, 2006, A1 Location in patent: Page/Page column 127-129

20
[ 5122-82-7 ]
[ 5858-17-3 ]
[ 64310-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; acetone;	EXAMPLE 8 1-adamantyl 3,4-dichlorophenylthiomethyl ketone 1-adamantyl bromomethyl ketone (1.3 g.), 1.1 g. of <strong>[5858-17-3]3,4-dichlorothiophenol</strong> and 800 mg. of anhydrous potassium carbonate in 30 ml. of acetone are stirred at reflux overnight. The solvent is then removed and 60 ml. of water is added to the reaction mixture. The product is filtered off, washed with water and recrystallized from methanol to yield 1-adamantyl 3,4-dichlorophenylthiomethyl ketone, M.P. 105-110.5 C.

Reference： [1]Patent: US4036975,1977,A

21
[ 5122-82-7 ]
[ 131242-36-9 ]
[ 393128-84-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine In acetonitrile at 20℃;	13 To a solution of adamantan-1-yl bromomethyl ketone (514 mg, 2.0 mmol) in acetonitrile (8 mL) was added pyrimidine-2 -thiol (249 mg, 2.1 mmol), followed by triethylamine (1 mL). The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as white solid (510 mg, 88%). mp 100-101 °C; TLC single spot at Rf. 0.28 (20% hexane/DCM); 1H NMR (270 MHz, CDCl3) δ 1.69-1.82 (6H, m, 3 x CH2), 1.94 (6H, d, J = 2.7 Hz, 3 x CH2), 2.07 (3H, broad, 3 x CH), 4.19 (2H, s, CH2), 6.93 (IH, t, J= 4.9 Hz, ArH), and 8.45 (2H, d, J= 4.9 Hz, ArH);LC/MS (ESI) m/z 311 (M* +Na), ), tr = 1.02 min in 5 % water-methanol; HRMS (ESI) ceded, for Ci6H2]N2OS (M* +H) 289.1375, found 289.1360; HPLC tr = 2.73min (>99 %) in 10% water-acetonitrile.
	Stage #1: 2-sulfanylpyrimidine With sodium carbonate In ethanol; water at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-adamantyl bromomethyl ketone In ethanol; water at 20℃; for 3h; Inert atmosphere;

Reference： [1]Current Patent Assignee: IPSEN SA - WO2009/106817, 2009, A2 Location in patent: Page/Page column 68
[2]Kang, Lei; Wang, Fang; Zhang, Jinlong; Yang, Huameng; Xia, Chungu; Qian, Jinlong; Jiang, Gaoxi [Organic Letters, 2021, vol. 23, # 5, p. 1669 - 1674]

22
[ 75-15-0 ]
[ 6926-58-5 ]
[ 5122-82-7 ]
[ 1185752-96-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: carbon disulfide; 4,4-dimethylthiosemicarbazide With triethylamine In N,N-dimethyl-formamide at 20 - 60℃; for 6h; Reflux; Stage #2: 1-adamantyl bromomethyl ketone In N,N-dimethyl-formamide at 20℃;	104 To a solution of N,N-dunethylhydrazinecarbothioamide (477 mg, 4 mmol) in DMF (6 mL) triethylamine (1 mL) was added, followed by the dropwise addition of CS2 (0.4 mL). The mixture was stirred at rt overnight and then at 60 °C for 5 h, cooled to room temperature. Adamantan-1-yl bromomethyl ketone (514 mg, 2.0 mmol) was added. The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product. Purification with flash column (DCM-ethyl acetate; gradient elution) yielded the title compound as an off-white solid (365 mg, 54 %). mp 150-151 °C; TLC single spot at Rf. 0.31 (25 % EtOAc/DCM); 1H NMR (270 MHz, CDCl3) δ 1.65-1.82 (m, 6H, 3 x CH2), 1.85 (d, J= 2.8 Hz, 6H, 3 x CH2), 2.03 (br, 3H, 3 x CH), 3.11 (s, 6H, 2 x CH3) and 4.40 (s, 2H, CH2); LC/MS (ESI) m/z 338 (M+H)+; tr = 2.23 min in 10 % water-methanol; HRMS (ESI) calcd. for C16H24N3OS2 (M+H)+ 338.1361, found 338.1353; HPLC tr = 2.43 min (99 %) in 10% water-acetonitrile.

Reference： [1]Current Patent Assignee: IPSEN SA - WO2009/106817, 2009, A2 Location in patent: Page/Page column 107

23
[ 18368-57-5 ]
[ 5122-82-7 ]
[ 1185752-24-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine; In acetonitrile; at 20℃;	To a solution of adamantan-1-yl bromomethyl ketone (514 mg, 2.0 mmol) in acetonitrile (10 mL) was added <strong>[18368-57-5]6-methylpyridine-2-thiol</strong> (275 mg, 2.2 mmol), followed by triethylamine (1 mL). The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as white solid (538 mg, 89%). mp 115.5-116.5 CTLC single spot at Rf. 0.75 (25 % EtOAc/hexane); 1H NMR (270 MHz, CDCl3) delta 1.68- 1.82 (6H, m, 3 x CH2), 1.95 (6H, d, J= 2.7 Hz, 3 x CH2), 2.07 (3H, broad, 3 x CH), 2.43 (3H, s, CH3), 4.22 (2H, s, CH2), 6.78 (IH, d, J = 7.9 Hz, ArH), 7.03 (IH, d, J= 7.9 Hz, ArH) and 7.33 (IH, t, J= 7.9 Hz, ArH); LC/MS (ESI) m/z 302 (M++H); tr = 1.60 min in 5 % water-methanol; HRMS (ESI) calcd. for C]8H24NOS (M+H-H) 302.1579, found 302.1583; HPLC tr = 4.45 min (>99 %) in 10% water-acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629
[2]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 73

24
[ 2637-34-5 ]
[ 5122-82-7 ]
[ 710311-13-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In acetonitrile at 20℃;
99%	With triethylamine In acetonitrile at 20℃;	12 To a solution of adamantan-1-yl bromomethyl ketone (514 mg, 2.0 mmol) in acetonitrile (8 mL) was added pyridine-2-thiol (244 mg, 2.1 mmol), followed by triethylamine (1 mL).20 The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried, over sodium sulfate and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as white solid (570 mg, 99%). mp 60-61 °C; TLC single spot at Rf. 0.69 (20%25 hexane/DCM); 1H NMR (270 MHz, CDCl3) δ 1.68-1.79 (6H, m, 3 x CH2), 1.94 (6H, d, J = 2.7 Hz, 3 x CH2), 2.07 (3H, broad, 3 x CH), 4.23 (2H, s, CH2), 6.93 (IH, ddd, J= 7.4, 4.9, 1.0 Hz, ArH), 7.21 (IH, dt, J= 8.2, 1.0 Hz, ArH), 7.44 (IH, ddd, J= 9.2, 7.4, 2.0 Hz, ArH) and 8.32 (IH, dq, J = 4.9, 1.0 Hz, ArH); LC/MS (ESI) m/z 288 (M++H); tr = 1.47 min in 5 % water-methanol; HRMS (ESI) calcd. for Ci7H22NOS (M++H) 288.1422, found30 288.1431; HPLC tr = 3.60 min (>99 %) in 10% water-acetonitrile.

Reference： [1]Location in patent: experimental part Su, Xiangdong; Pradaux-Caggiano, Fabienne; Vicker, Nigel; Thomas, Mark P.; Halem, Heather; Culler, Michael D.; Potter, Barry V.L. [ChemMedChem, 2011, vol. 6, # 9, p. 1616 - 1629]
[2]Current Patent Assignee: IPSEN SA - WO2009/106817, 2009, A2 Location in patent: Page/Page column 67

25
[ 5122-82-7 ]
[ 13183-79-4 ]
[ 710311-12-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In acetonitrile; at 20℃;	To a solution of adamantan-1-yl bromomethyl ketone (463 mg, 1.8 mmol) in acetonitrile (20 mL) l-methyl-lH-tetrazole-5-thiol (232 mg, 2.0 mmol) was added, followed by triethylamine (1 mL). The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product. Purification with flash column (DCM-ethyl acetate; gradient elution) yielded the title compound as a white solid (395 mg, 75 %). mp 112-113 C; TLC single spot at Rf. 0.69 (10 % EtOAc/DCM); 1H NMR (270 MHz, CDCl3) delta 1.62-1.80 (6H, m, 3 x CH2), 1.88 (6H, d, J= 2.8 Hz, 3 x CH2), 2.07 (3H, broad, 3 x CH), 3.97 (3H, s, CH3) and 4.53 (2H, s, CH2); LC/MS (ESI) m/z 293 (M+H)+; tr = 1.76 min in 10 % water-methanol; HRMS (ESI) calcd. for C14H21N4OS (M+H)+ 293.1436, found 293.1417; HPLC tr = 2.01 min (>99 %) in 10% water-acetonitrile

Reference： [1]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 101

26
[ 4556-23-4 ]
[ 5122-82-7 ]
[ 1185752-26-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In acetonitrile at 20℃;
86%	With triethylamine In acetonitrile at 20℃;	27 To a solution of adamantan-1-yl bromomethyl ketone (514 mg, 2.0 mmol) in acetonitrile (10 mL) was added pyridine-4-thiol (244 mg, 2.2 mmol), followed by triethylamine (1 mL). The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product. Purification with flash column (hexane-ethyl acetate; gradient elution) yielded the title compound as white solid (494 mg, 86 %). mp 114-115 °C; TLC single spot at Rf 0.32 (25 % EtOAc/DCM); 1H NMR (270 MHz, CDCl3) δ 1.70-1.82 (6H, m, 3 x CH2), 1.90 (6H, d, J = 2.8 Hz, 3 x CH2), 2.08 (3H, broad, 3 x CH), 4.01 (2H, s, CH2), 7.08 (2H, dd, J = 4.7, 1.8 Hz, ArH) and 8.38 (2H, dd, J= 4.7, 1.8 Hz, ArH); LC/MS (ESI) m/z 288 (M+H-H); tr = 1.12 min in 5 % water-methanol; HRMS (ESI) calcd. for C17H22NOS (M+H-H) 288.1422, found 288.1420; HPLC tr = 2.64 min (>99 %) in 10% water-acetonitrile.

27
[ 5122-82-7 ]
[ 29490-19-5 ]
[ 393128-76-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine; In acetonitrile; at 20℃;	To a solution of adamantan-1-yl bromomethyl ketone (643 mg, 2.5 mmol) in acetonitrile (20 mL) was added 5-methyl-l,3,4-thiadiazole-2-thiol (331 mg, 2.5 mmol), followed by triethylamine (1 mL). The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. Purification with flash <n="98"/>column (DCM-ethyl acetate; gradient elution) yielded the title compound as white solid (670 mg, 87 %). mp 102-105 C; TLC single spot at Rf. 0.37 (8 % EtOAc/DCM); 1H NMR (270 MHz, CDCl3) delta 1.65-1.80 (6H, m, 3 x CH2), 1.90 (6H, d, J = 2.8 Hz, 3 x CH2), 2.06 (3H, br, 3 x CH), 2.69 (3H, s, CH3) and 4.48 (2H, s, CH2); LC/MS (ESI) m/z 309 (M++H); tr = 2.58 min in 10 % water-methanol; HRMS (ESI) calcd. for C15H20N2OS2Na (MVNa) 331.0915, found 331.0873; HPLC tr = 2.67 min (>99 %) in 10% water-acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1439 - 1451
[2]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 95-96

28
[ 74115-12-1 ]
[ 5122-82-7 ]
[ 1185752-56-0 ]

Yield	Reaction Conditions	Operation in experiment
75.5%	With potassium carbonate; In acetone; at 20℃; for 20h;	K2CO3 (108 mg, 0.78 mmol) was added to a solution of 1-adamantyl bromomethyl ketone (100 mg, 0.39 mmol) and 5-chloro-3-pyridinol (50 mg, 0.39 mmol) in acetone (5 mL) at <n="89"/>room temperature. The reaction was stirred for 2Oh then was quenched by addition of water. The extraction was conducted with EtOAc (x2) then the organic phase was washed with brine and dried over MgSO4. The crude residue was the purified by flash chromatography (hexane/EtOAc 0-30% gradient) to afford the title compound (89.9 mg, 75.5%) as pearl white solid. TLC single spot at R/0.34 (hexane/EtOAc 7:3); Mp = [126.5- 128.0 0C]; 1H NMR (270 MHz, CDCl3): delta 1.63-1.82 (m, 6H), 1.88 (d, J = 2.5 Hz, 6H), 2.07 (s br, 3H), 4.89 (s, 2H), 7.06-7.12 (m, IH), 8.12 (d, J = 2.2 Hz, IH), 8.17 (d, J = 1.4 Hz, IH); LC/MS (APCI) m/z 328 (M++Na); Accurate Mass: calculated (M++H) 306.1255; found 306.1244; HPLC tr = 2.82 min (100%) in 10% water-acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629
[2]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 86-87

29
[ 5122-82-7 ]
[ 120277-47-6 ]
[ 1185752-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 20℃; for 72.0h;	A mixture of <strong>[120277-47-6](4-methoxypyridin-3-yl)methanol</strong> (178 mg,1.28 mmol), 1-adamantyl bromomethylketone (275 mg, 1.07 mmol) and potassium carbonate (888 mg, 6.43 mmol) in acetone (8mL) was stirred at room temperature over 72h. The mixture quenched with water, extracted with EtOAc (x2), washed with water (x2) and brine, dried over MgSO4 and concentrated under vacuum. The crude was purified by flash chromatography on silica gel using a gradient of 0-5% methanol in DCM) to give the expected product (96.5 mg, 29%) as off-white slurry solid. TLC single spot at R/ 0.49 (MeOH/DCM 5:95); 1HNMR (CDCl3, 270MHz) delta: 1.59-1.75 (m, 6H), 1.77 (d, J= 2.8 Hz, 6H), 1.99 (s br, 3H),3.89 (s, 3H), 4.26 (s, 2H), 4.46 (s, 2H), 6.71 (d, J= 8.5 Hz, IH), 7.63 (dd, J= 8.5, 2.5 Hz,IH), 8.06 (d, J = 2.5 Hz, IH); LC/MS (APCI) m/z 316 (M++H); Accurate Mass: calculated (M++H) 316.1907; found 316.1892; HPLC tr = 2.89 min (94%) in 10% water- acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629
[2]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 98

30
[ 51984-46-4 ]
[ 5122-82-7 ]
[ 1185752-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetone; at 20℃; for 15h;	A mixture of <strong>[51984-46-4](3-methoxypyridin-2-yl)methanol</strong> (128 mg, 0.92 mmol), 1-adamantyl bromomethylketone (198 mg, 0.77 mmol) and caesium carbonate (500 mg, 1.53 mmol) in acetone (1OmL) was stirred at room temperature for 15h. The mixture was filtered, concentrated under vacuum and purified by flash chromatography (0-25percent-50percent Petrol <n="101"/>ether/EtOAc) to give the expected product (161 mg, 66.2percent yield) as clear yellow oil. Single TLC spot at R/0.6 (Pet. ether/EtOAc 5:5); 1H NMR (CDCl3, 270 MHz): .pound.1.63- 1.77 (m,6H), 1.83 (br s, 6H), 2.03 (br s, 3H), 3.88-3.91 (m, 3H), 4.42-4.46 (m, 2H), 4.57 (d, J= 3.0 Hz, 2H), 6.62 (dd, J= 8.4, 2.9 Hz, IH), 7.00-7.06 (m, IH), 7.57-7.60 (m, IH); ); LC/MS (ESI) t = 2.20 min m/z 316 (M++H); HPLC t = 3.05 min (91.83percent) in 10percent water-acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629
[2]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 98-99

31
[ 386704-04-7 ]
[ 5122-82-7 ]
[ 1185752-55-9 ]

Yield	Reaction Conditions	Operation in experiment
29%	Stage #1: 6-(trifluoromethyl)pyridin-3-ylmethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 1-adamantyl bromomethyl ketone In tetrahydrofuran; mineral oil at 0 - 20℃;
28%	Stage #1: 6-(trifluoromethyl)pyridin-3-ylmethanol With sodium hydride In tetrahydrofuran at 0℃; Stage #2: 1-adamantyl bromomethyl ketone In tetrahydrofuran for 24h;	56 NaH (23 mg, 1.56 mmol) was added neat at 0 0C to a solution of 6- (trifluoromethyl)pyridm-3 -methanol (0.098 mL, 0.78 mmol) in dry THF (5 mL) and stirred 30 min. Then 1-adamantyl bromomethyl ketone (200 mg, 0.78 mmol) was added via a cannula to the suspension and the reaction was stirred for 24h. The reaction was quenched by addition of water. The extraction was conducted with EtOAc (x2) then the organic phase was washed with brine and dried over MgSO4. The crude residue was the purified by flash chromatography (hexane/EtOAc 0-20% gradient) to afford the title compound (76.6 mg, 28%) as white solid. TLC single spot at R/ 0.31 (hexane/EtOAc 7:3); Mp = [105.7-109.8 0C]; 1H NMR (270 MHz, CDCl3): δ 1.58-1.80 (m, 6H), 1.80 (d, J = 2.7 Hz, 6H), 2.01 (s br, 3H), 4.38 (s, 2H), 4.63 (s, 2H), 7.65 (d, J = 7.9 Hz, IH), 7.93 (dd, J = 7.9, 1.4 Hz, IH), 8.65 (s br, IH); LC/MS (APCI) m/z 376 (M++Na); Accurate Mass: calculated (M*+H) 354.1675; found 354.1664; HPLC tr = 3.22 min (96.6%) in 5% water- methanol.

32
[ 5122-82-7 ]
[ 38942-50-6 ]
[ 948153-49-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With triethylamine; In acetonitrile; at 20℃;	To a solution of adamantan-1-yl bromomethyl ketone (298 mg, 1.16 mmol) in acetonitrile(8 mL) was added 4,5-dimethyl-4H-l,2,4-triazole-3-thiol (150 mg, 1.16 mmol), followed by triethylamine (1 mL). The mixture was stirred at ambient temperature overnight, partitioned between ethyl acetate and saturated sodium carbonate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product. Purification with flash column (DCM-methanol; gradient elution) yielded the title compound as a white solid (190 mg, 54 %). mp 113-114 C; TLC single spot at Rf. 0.20 (8 % CH3OH/DCM); 1H NMR (270 MHz, CDCl3) delta 1.62-1.80 (m, 6H, 3 x CH2), 1.85 (d, J= 2.8 Hz, 6H, 3 x CH2), 2.15 (broad, 3H, 3 x CH), 2.39 (s, 3H, CH3), 3.49 (s, 3H, CH3) and 4.39 (s, 2H, CH2); LC/MS (ESI) m/z 306 (M+H)+; tr = 1.58 min in 10 % water-methanol; HRMS (ESI) calcd. for Ci6H24N3OS (M+H)+ 306.1640, found 306.1627; HPLC tr = 1.82 min (>99 %) in 10% water-acetonitrile.

Reference： [1]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 99
[2]ChemMedChem,2011,vol. 6,p. 1439 - 1451

33
[ 5122-82-7 ]
[ 33252-63-0 ]
[ 1185752-54-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In acetone; at 20℃; for 20h;	K2CO3 (107 mg, 0.78 mmol) was added to a solution of 1-adamantyl bromomethyl ketone (100 mg, 0.39 mmol) and 5-tri(fluoromethyl)-2-pyridinol (64 mg, 0.39 mmol) in acetone (5 mL) at room temperature. The reaction was stirred for 2Oh at room temperature then was quenched by addition of water. The extraction was conducted with EtOAc (x2) then the organic phase was washed with brine and dried over MgSO4. The crude residue was the purified by flash chromatography (hexane/EtOAc 0-20% gradient) to afford the title compound (118.6 mg, 90%) as white solid. TLC single spot at R/ 0.22 (hexane/EtOAc 7:3); Mp = [101.7-103.5 0C]; 1H NMR (270 MHz, CDCl3): £2.65-2.83 (m, 2H), 1.93 (d, J = 2.7 Hz, 6H), 2.08 (br s, 3H), 4.85 (s, 2H), 6.58 (d br, J = 10.4 Hz, IH), 7.48-7.40 (m, 2H); LC/MS (APCI) m/z 338 (M+-H), 339 (M+); Accurate Mass: calculated (M++H) 340.1519; found 340.1521; HPLC tr = 2.20 min (100%) in 10% water-acetonitrile.

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629
[2]Patent: WO2009/106817,2009,A2 .Location in patent: Page/Page column 86

34
[ 5122-82-7 ]
[ 16834-13-2 ]
4Br^(1-)*C₈₈H₉₄N₈O₄⁽⁴⁺⁾ [ No CAS ]

Reference： [1]Bioorganic Chemistry,2010,vol. 38,p. 159 - 164

35
[ 349-75-7 ]
[ 5122-82-7 ]
[ 1239465-35-0 ]

Reference： [1]ChemMedChem,2010,vol. 5,p. 1026 - 1044

36
[ 5122-82-7 ]
[ 16375-90-9 ]
[ 1239465-31-6 ]

Reference： [1]ChemMedChem,2010,vol. 5,p. 1026 - 1044

37
[ 5122-82-7 ]
[ 3964-54-3 ]
[ 1239465-30-5 ]

Reference： [1]ChemMedChem,2010,vol. 5,p. 1026 - 1044

38
[ 5122-82-7 ]
[ 80518-57-6 ]
[ 1335146-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In acetonitrile at 20℃;	49A Ethyl 4-(piperazin-1-yl)benzoate (100 mg), 1-admantyl bromomethyl ketone (110 mg) and sodium carbonate (46 mg) were suspended in anhydrous acetonitrile (2 mL). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 aqueous solution, and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4, filtered and concentrated to afford the title compound

Reference： [1]Current Patent Assignee: ABBVIE INC; ABBOTT LABORATORIES INC - US2011/237553, 2011, A1 Location in patent: Page/Page column 34

39
[ 18368-57-5 ]
[ 5122-82-7 ]
[ 1185752-31-1 ]
[ 1185752-30-0 ]

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629
[2]Patent: WO2009/106817,2009,A2

40
[ 5122-82-7 ]
[ 76041-72-0 ]
[ 1185752-65-1 ]

Reference： [1]ChemMedChem,2011,vol. 6,p. 1616 - 1629

41
[ 14542-12-2 ]
[ 5122-82-7 ]
[ 1330778-47-6 ]

Reference： [1]ChemMedChem,2011,vol. 6,p. 1439 - 1451

42
[ 13750-63-5 ]
[ 5122-82-7 ]
[ 1330778-48-7 ]

Reference： [1]ChemMedChem,2011,vol. 6,p. 1439 - 1451

43
[ 5122-82-7 ]
[ 16834-13-2 ]
meso-tetra[1-(1-adamantyl methyl ketone)-4-pyridyl]porphyrin [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 1807 - 1810

44
[ 5122-82-7 ]
[ 535-80-8 ]
2-(adamantan-1-yl)-2-oxoethyl 3-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
73%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

45
[ 5122-82-7 ]
[ 74-11-3 ]
2-(adamantan-1-yl)-2-oxoethyl 4-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
75%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

46
[ 50-84-0 ]
[ 5122-82-7 ]
2-(adamantan-1-yl)-2-oxoethyl 2,4-dichlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
85%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

47
[ 5122-82-7 ]
[ 99-04-7 ]
2-(adamantan-1-yl)-2-oxoethyl 3-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
75%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

48
[ 5122-82-7 ]
[ 99-94-5 ]
2-(adamantan-1-yl)-2-oxoethyl 4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
81%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

49
[ 5122-82-7 ]
[ 579-75-9 ]
2-(adamantan-1-yl)-2-oxoethyl 2-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
80%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

50
[ 5122-82-7 ]
[ 586-38-9 ]
2-(adamantan-1-yl)-2-oxoethyl 3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
74%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

51
[ 5122-82-7 ]
[ 100-09-4 ]
2-(adamantan-1-yl)-2-oxoethyl 4-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
80%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

52
[ 5122-82-7 ]
[ 552-16-9 ]
2-(adamantan-1-yl)-2-oxoethyl 2-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
70%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

53
[ 5122-82-7 ]
[ 121-92-6 ]
2-(adamantan-1-yl)-2-oxoethyl 3-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
72%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

54
[ 5122-82-7 ]
[ 62-23-7 ]
2-(adamantan-1-yl)-2-oxoethyl 4-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

55
[ 5122-82-7 ]
[ 99-05-8 ]
2-(adamantan-1-yl)-2-oxoethyl 3-aminobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
70%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

56
[ 5122-82-7 ]
[ 150-13-0 ]
2-(adamantan-1-yl)-2-oxoethyl 4-aminobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

57
[ 98-98-6 ]
[ 5122-82-7 ]
2-(adamantan-1-yl)-2-oxoethyl 2-pyridinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	3.1. Synthesis General procedure: 1-Adamantyl methyl ketone was refluxed with N-bromo succinimide and petroleum ether in methanol at 333 K for two hours. The resultant 1-adamantyl bromomethyl ketone (1) precipitate was filtered and recrystallized with ethanol. After that, 1-adamantyl bromomethyl ketone (1) (0.51 g, 0.002 mol) was reacted with the corresponding carboxylic acid (0.003 mol) with the presence of potassium carbonate in DMF (8 mL) and stirred at room temperature for about 3 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction completed, the reaction mixture was poured into ice-cooled water and kept stirring for 10 min. The solid obtained was filtered out, washed successively with distilled water and recrystallized from acetone after it dried [20]. All targeted compounds were synthesized in good yield and high purity. Suitable single-crystal specimens were obtained from various types of solvents, as described below. The chemical structures were characterized by using FTIR and NMR spectroscopies. The crystal structures for all compounds except 2m and 2q were determined by single-crystal X-ray diffraction analysis.
76%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kumar, C.S. Chidan; Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Loh, Wan-Sin; Quah, Ching Kheng; Lim, Gin Keat; Chandraju, Siddegowda; Fun, Hoong-Kun [Molecules, 2015, vol. 20, # 10, p. 18827 - 18846]
[2]Kwong, Huey Chong; Mah, Siau Hui; Chia, Tze Shyang; Quah, Ching Kheng; Lim, Gin Keat; Kumar, C. S. Chidan [Molecules, 2017, vol. 22, # 6]

58
[ 1014-25-1 ]
[ 5122-82-7 ]
6-(adamantan-1-yl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With magnesia; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 60℃; for 2h;Green chemistry;	General procedure: A mixture of 5-alkyl/aryl-2-amino1,3,4-thiadiazole (0.01 mol), 1-adamantyl bromomethylketone(0.01 mol) and nano magnesium oxide (0.001 mol) in 2 ml of 1-Butyl-3-methylimidazolium tetrafluoroborate [BMIM]+[BF4]- was stirred at 60C for the appropriate time (Table 2).After completion of the reaction, as determined by TLC, the reaction mixture was cooled down and then quenched into ice water. The product was extracted from the water layer by 3×5 mL diethyl ether, dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography employing a column of 30 mm diameter using 60-120 silica gel and hexane/ethyl acetate (80:20) as mobile phase. All new compounds exhibited spectral properties consistent with the assigned structures (S2 Data).

Reference： [1]PLoS ONE,2015,vol. 10

59
[ 5122-82-7 ]
[ 63617-18-5 ]
6-(adamantan-1-yl)-2-(4-methoxybenzyl)imidazo[2,1-b][1,3,4]thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With magnesia; 1-butyl-3-methylimidazolium Tetrafluoroborate at 60℃; for 2h; Green chemistry;	Typical procedure for the synthesis of AITs General procedure: A mixture of 5-alkyl/aryl-2-amino1,3,4-thiadiazole (0.01 mol), 1-adamantyl bromomethylketone(0.01 mol) and nano magnesium oxide (0.001 mol) in 2 ml of 1-Butyl-3-methylimidazolium tetrafluoroborate [BMIM]+[BF4]- was stirred at 60°C for the appropriate time (Table 2).After completion of the reaction, as determined by TLC, the reaction mixture was cooled down and then quenched into ice water. The product was extracted from the water layer by 3×5 mL diethyl ether, dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography employing a column of 30 mm diameter using 60-120 silica gel and hexane/ethyl acetate (80:20) as mobile phase. All new compounds exhibited spectral properties consistent with the assigned structures (S2 Data).

Reference： [1]Anusha, Sebastian; Baburajeev; Mohan, Chakrabhavi Dhananjaya; Mathai, Jessin; Rangappa, Shobith; Mohan, Surender; Chandra; Paricharak, Shardul; Mervin, Lewis; Fuchs, Julian E.; Mahedra; Bender, Andreas; Basappa; Rangappa, Kanchugarakoppal S. [PLoS ONE, 2015, vol. 10, # 10]

60
[ 5122-82-7 ]
[ 5241-64-5 ]
C₂₈H₃₆N₂O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1529 - 1535

61
[ 5122-82-7 ]
[ 76115-06-5 ]
C₃₈H₃₆O₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 6131 - 6136

62
[ 108-47-4 ]
[ 5122-82-7 ]
[ 2484990-58-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	In acetonitrile at 20℃;	Synthesis of 1-[(adamantan-1-yl)-2-oxoethyl]pyridiniumbromides 1a-h (General method) General procedure: The corresponding pyridine (41 mmol) was added to a solution of 1-(adamantan-1-yl)-2-bromoethanone (9.80 g, 38.8 mmol) in MeCN (50 ml). The resulting mixture was stirred atroom temperature overnight. The formed precipitate was filtered off and purified by recrystallization from MeCN.

Reference： [1]Shadrikova, Vera А.; Golovin, Evgeny V.; Rybakov, Victor B.; Klimochkin, Yuri N. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 7, p. 898 - 908][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 7, p. 898 - 908,11]

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Precautionary Statements-General
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P321
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P342	If experiencing respiratory symptoms:
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P378
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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.
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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.
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Physical hazards
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H200	Unstable explosive
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H311	Toxic in contact with skin
H312	Harmful in contact with skin
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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. 5122-82-7 ] {[proInfo.proName]}

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[ 5122-82-7 ] Synthesis Path-Upstream 1~2

[ 5122-82-7 ] Synthesis Path-Downstream 1~62

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Aliphatic Cyclic Hydrocarbons

Bromides

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