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Josephine Bicknell ; Sidhaesh A. Agarwal ; Kyle J. Petersen , et al. DOI:

Abstract: Lipophilic aggregation using adamantanes is a widely exploited molecular property in medicinal and materials chemistry. Adamantanes are traditionally installed to molecular units via covalent bonds. However, the noncovalent installation of adamantanes has been relatively underexplored and presents the potential to bring properties associated with adamantanes to molecules without affecting their intrinsic properties (e.g., pharmacophores). Here, we systematically study a series of adamantanecarboxylic acids with varying substitution levels of methyl groups and their cocrystals with bipyridines. Specifically, single-crystal X-ray diffraction shows that while the directionality of single-component adamantanes is notably sensitive to changes in methyl substitution, hydrogen-bonded cocrystals with bipyridines show consistent and robust packing due to π-stacking predominance. Our observations are supported by Hirshfeld surface and energy framework analyses. The applicability of cocrystal formation of adamantanes bearing carboxylic acids was used to generate the first cocrystals of adapalene, an adamantane-bearing retinoid used for treating acne vulgaris. We envisage our study to inspire noncovalent (i.e., cocrystal) installation of adamantanes to generate lipophilic aggregation in multicomponent systems.

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Product Details of [ 828-51-3 ]

CAS No. :828-51-3 MDL No. :MFCD00074720
Formula : C11H16O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JIMXXGFJRDUSRO-UHFFFAOYSA-N
M.W : 180.24 Pubchem ID :13235
Synonyms :

Calculated chemistry of [ 828-51-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.16
TPSA : 37.3 Ų

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) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 2.62
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 1.95
Consensus Log Po/w : 2.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.517 mg/ml ; 0.00287 mol/l
Class : Soluble
Log S (Ali) : -3.05
Solubility : 0.159 mg/ml ; 0.000885 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.32
Solubility : 8.65 mg/ml ; 0.048 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.76

Safety of [ 828-51-3 ]

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 [ 828-51-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 828-51-3 ]
  • Downstream synthetic route of [ 828-51-3 ]

[ 828-51-3 ] Synthesis Path-Upstream   1~20

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Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5013 - 5016
[2] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5013 - 5016
[3] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5013 - 5016
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Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5013 - 5016
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Reference: [1] Chemistry - A European Journal, 2005, vol. 11, # 1, p. 308 - 320
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  • [ 5511-18-2 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -10℃; for 0.5 h;
Stage #2: With ammonia In tetrahydrofuran; water at -10 - 20℃; for 0.5 h;
3-Aminomethyl-I-adamantanol Step 1: 1-Adamantanecarboxamide: To a stirred and cooled (-10 °C) solution of adamantane-1 -carboxylic acid (5.0 g, 27.74 mmol) and triethylamine (3.61 g, 33.27 mmol) in THF (80 ml) was added ethyl chloroformate (3.65 g, 36.06 mmol) to result in a white precipitate. The mixture was stirred at the same temperature for 30 min and 30 percent NH4OH (20 ml) was added. The reaction mixture was gradually warmed to room temperature and further stirred for 30 min. THF was evaporated under reduced pressure and the solid precipitated was filtered and washed with cold water to afford EPO <DP n="29"/>the desired product as a white solid (4.8 g, 97 percent); IR (KBr) 3515, 3422, 2899, 2853, 1634, 1596 cm"1; 1H NMR (300 MHz, DMSO-J6) δ 1.64-1.69 (m, 6H), 1.73-1.74 (m, 6H), 1.94 (brs, 3H), 6.68 (brs, IH), 6.94 (brs, IH).
87%
Stage #1: With 1,1'-carbonyldiimidazole In ethyl acetate at 20℃; for 0.333333 h;
Stage #2: With ammonium hydroxide In ethyl acetate at 20℃; for 0.333333 h;
Example B13
A solution of adamantane-1-carboxylic acid (2.00 g, 11.10 mmol) in EtOAc (20 mL) was treated with CDI (2.00 g, 12.33 mmol), stirred at RT for 20 minutes, treated with NH4OH (˜14M, 5 mL, ˜70 mmol) and stirred at RT for 20 minutes.
The mixture was concentrated to dryness, treated with satd.
NaHCO3 and the solids collected via filtration and dried to afford adamantane-1-carboxamide (1.74 g, 87percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.91 (s, 1H), 6.65 (s, 1H), 1.92 (m, 3H), 1.74-1.71 (m, 6H), 1.68-1.57 (m, 6H); MS (ESI) m/z: 180.1 (M+H+).
70%
Stage #1: for 3 h; Reflux
Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 1 h; Cooling with ice
General procedure: Adamantane-1-carboxylic acid (7.4 g, 41 mmol) was heated to reflux with thionyl chloride (15 mL) and DMF (2 drops) for 3 h. The excess thionyl chloride was distilled off under reduced pressure and the residual traces were removed in vacuo for 15 min. The residue was dissolved in THF (20 mL) and added to aqueous ammonia (30percent, 100 mL) with ice cooling and stirring. After stirring for 1 h at ambient temperature, the precipitate was filtered off, H2O (1 L) was added, followed by CH2Cl2 (200 mL) until the entire solid had dissolved. The organic layer was collected, dried (MgSO4) and evaporated in vacuo to give adamantane-1-carboxamide (5.15 g, 70percent over 2 steps) as a colourless solid; δH ( 200 MHz; CDCl3) 5.75 (2 H, br s), 2.05 (3 H, br s), 1.89–1.88 (6 H, m), 1.80–1.63 (6 H, m).
64% With diisobutylaluminium hydride; ammonium chloride In tetrahydrofuran at 66℃; for 16 h; Inert atmosphere General procedure: The solution of aminoalane reagent (prepared from 20 equiv. DIBAL-H in case of ester and lactonesubstrates or from 40 equiv. in case of carboxylic acid and amide substrates) was added to a solutionof carboxylic acid (1 eqiuv.) or its derivative (lactone, ester or amide, 1 equiv.) in anhydrous THF atroom temperature. Stirring was continued for 16 hours at 66 C. After this time, the reaction mixturewas cooled, quenched with aqueous solution of KHSO4 and the product was extracted with CHCl3.The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified by silica gel chromatography with hexane / ethyl acetateelution.

Reference: [1] Tetrahedron, 2018, vol. 74, # 12, p. 1207 - 1219
[2] Patent: WO2006/90244, 2006, A1, . Location in patent: Page/Page column 27-28
[3] ACS Chemical Neuroscience, 2014, vol. 5, # 5, p. 335 - 339
[4] Patent: US2014/275080, 2014, A1, . Location in patent: Paragraph 0372
[5] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631
[6] Organic Letters, 2018, vol. 20, # 19, p. 6046 - 6050
[7] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 828 - 830
[8] Synlett, 2015, vol. 26, # 16, p. 2288 - 2292
[9] Journal of the American Chemical Society, 1985, vol. 107, # 20, p. 5717 - 5722
[10] Synthesis, 2001, # 6, p. 914 - 918
[11] Synthesis, 2001, # 6, p. 914 - 918
[12] Chemical Communications, 1998, # 21, p. 2297 - 2298
[13] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 4, p. 287 - 291[14] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 4, p. 454 - 458
[15] Chemistry - A European Journal, 2016, vol. 22, # 15, p. 5156 - 5159
[16] Chemistry - A European Journal, 2016, vol. 22, # 39, p. 14042 - 14047
[17] Molecules, 2018, vol. 23, # 2,
[18] Patent: WO2008/106128, 2008, A2,
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  • [ 75-05-8 ]
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Reference: [1] Synlett, 2005, # 13, p. 2089 - 2091
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Reference: [1] Supramolecular Chemistry, 2017, vol. 29, # 2, p. 120 - 128
  • 7
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  • [ 56674-87-4 ]
  • [ 81968-77-6 ]
  • [ 42711-75-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 67 - 73
  • 8
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  • [ 39269-10-8 ]
Reference: [1] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 4119 - 4120
[2] Synthetic Communications, 1984, vol. 14, # 2, p. 113 - 120
[3] Soft Matter, 2016, vol. 12, # 28, p. 6148 - 6156
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Reference: [1] Patent: EP897747, 1999, A1,
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  • [ 281-23-2 ]
  • [ 768-95-6 ]
  • [ 828-51-3 ]
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  • [ 39269-10-8 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 2, p. 222 - 223
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  • [ 5001-18-3 ]
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Reference: [1] Patent: JP5790430, 2015, B2, . Location in patent: Paragraph 0032; 0033; 0036
  • 12
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  • [ 38584-37-1 ]
Reference: [1] Patent: WO2015/87262, 2015, A1,
  • 13
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  • [ 42711-75-1 ]
YieldReaction ConditionsOperation in experiment
92.6% at 10 - 35℃; for 3.5 h; 30.2 g of 1-adamantanol (purity 99percent) was charged in a glass flask equipped with a stirrer, a thermometer, a dropping funnel and a Dimroth as a reaction device, and 215.2 g of 96 mass percent concentrated sulfuric acid was added. After stirring at room temperature to confirm dissolution of the raw material, 9.3 g of formic acid was added dropwise over 15 minutes so that the liquid temperature was kept in the range of 10 to 20 ° C. by cooling the flask. After completion of the dropwise addition, the reaction was carried out at a reaction temperature of 35 ° C. for 3 hours.When progress of the reaction was confirmed by GC, 1-adamantanecarboxylic acid was produced at a conversion of 1-adamantanol of 100percent. Thereafter, while cooling the flask again, 23.1 g of 70percent nitric acid was added dropwise over 30 minutes while keeping the liquid temperature in the range of 10 to 20 ° C. After completion of the dropwise addition, the reaction was carried out at a reaction temperature of 35 ° C. for 3 hours. When progress of the reaction was confirmed by GC, the conversion of 1-adamantanecarboxylic acid was 100percent, and 3-hydroxyadamantane-1-carboxylic acid was formed. As a refining device, a stirrer, A glass flask equipped with a thermometer, 90.2 g of sodium hydroxide, 35.5 g of sodium sulfite and 812 g of ion-exchanged water were charged to prepare a mixed solution of sodium hydroxide and sodium sulfite, and the flask was cooled. To the above mixed solution, 277.8 g of a reaction solution of 3-hydroxy-1-adamantanecarboxylic acid was added so that the liquid temperature remained at 40 ° C. or less, and the precipitated white crystals were separated by filtration and washed with water. Further, the obtained crystals were dried under reduced pressure at 40 ° C. for 8 hours to obtain 35.8 g (yield 92.6percent) of white crystals of 3-hydroxyadamantane-1-carboxylic acid. The high boiling point by-product (high molecular weight by-product) in the crystal was measured by GPC-RI and found to be 1.28percent.
91% With sulfuric acid; nitric acid In water at 0 - 5℃; for 26 h; Concentrated sulfuric acid (20 mL) was stirred and cooled down to 0°C followed by adding nitric acid (2.5 mL,65 percent w/w aqueous solution), then 1-adamantanecarboxylic acid (5.0 g, 0.028 mol) was added to solution in batches during 1h. Thenceforth, the mixture was stirred at 0~5°C for 20 h. After that, crushed ice (100 g) was added and stirred at 5°C for another 5 h to give plentiful white solid, which was filtered and recrystallized by propanone/water, then dried to produce 3-hydroxy-1-adamantanecarboxylic acid (4.96 g, 91percent yield). Mp 199~200°C; IR (KBr, cm-1): 3440, 2953,1721, 1709, 1338, 1268, 1249, 1227, 1119, 1018, 722; ESI–MS (m/z): 195 [M]-; 1H NMR (400 MHz, DMSO) : 1.45-1.52 (m, 2H), 1.53-1.57 (m, 4H), 1.64-1.65 (m, 6H), 2.11-2.12 (m, 2H), 4.45 (brs, 1H, OH), 11.97 (brs, 1H, COOH).
89% With sulfuric acid; nitric acid In water at 0℃; for 15.5 h; A solution of concentrated sulfuric acid (20 mL) and nitric acid (2.5 mL, 65 percent w/w aqueous solution) was stirred at 0 °C, then 1-adamantanecarboxylic acid(1) (5.0 g, 0.028 mol) was added portionwise during half an hour. Thereafter, the mixture was stirred at 0 °C for 15 h. Afterwards, distilled water (100 mL) was added at 10 °C and stirred for another 4 h to produce a lot of white solid, which was filtered and recrystallized from propanone/water, then dried to afford compound 2 (4.88 g, 89 percent yield). M.p. 199–200 °C; IR(KBr, cm-1): 3450, 2900, 1700, 1250, 1100, 580; ESI -MS (m/z): 195[M]-.
97.4 g at -5 - 1℃; Concentrated sulphuric acid (400 mL) was charged to a round bottom flask at 25 °C and cooled to -10°C. Nitric acid (50 mL; 50percent w/w aqueous solution) was added at -10°C to 0°C over 1 hour, followed by the addition of tricyclo[3.3.1.13'7]decane-l-carboxylic acid (Formula IX; 100 g) in portions at -5°C to 0°C over 1 hour, then further stirred for 4 hours at -1°C to 1°C. A mixture of concentrated sulfuric acid and 50percent w/w aqueous solution of nitric acid in a 1 : 1 ratio (25 mL each) was added to the reaction mixture over 30 minutes, stirred for 12 hours to 13 hours at -1°C to 1°C, followed by the addition of water (2500 mL) at 0°C to 10°C, and further stirred for 4 hours at 10°C to 12°C to obtain a solid. The obtained solid was filtered, washed with chilled water (500 mL), dried under suction for 2 hours, and then air dried in an oven for 10 hours at 40°C to 45 °C to obtain the title compound. Yield: 97.4 g
30 g at 10 - 35℃; for 5.5 h; A glass flask was equipped with a stirrer, a thermometer, a dropping funnel and a Dimroth condenser for use as a reaction apparatus and was charged with 1-adamantanol (purity: 99percent, 30.2 g), followed by addition of 96percent by mass concentrated sulfuric acid (215.2 g). After the mixture was stirred at room temperature and the starting material was confirmed to be dissolved, the flask was cooled to maintain the solution temperature within the range of 10° C. to 20° C. and formic acid (9.3 g) was added dropwise thereto over 30 minutes. After completion of the dropwise addition, the mixture was reacted at a reaction temperature of 35° C. for 3 hours. When the progress of the reaction was confirmed by GC, the conversion of 1-adamantanol was found to be 100percent and 1-adamantane carboxylic acid was generated in a reaction yield of 98.9percent. Subsequently, while cooling the flask again to maintain the solution temperature within the range of 10° C. to 20° C., 70percent nitric acid (23.1 g) was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was reacted at a reaction temperature of 35° C. for 5 hours. When the progress of the reaction was confirmed by GC, the conversion of 1-adamantane carboxylic acid was found to be 100percent and 3-hydroxy adamantane-1-carboxylic acid was generated in a reaction yield of 99.2percent. A glass flask was equipped with a stirrer and a thermometer for use as a purification apparatus and was charged with sodium hydroxide (90.2 g), sodium sulfite (35.5 g) and ion exchanged water (812 g) to prepare a mixed solution of sodium hydroxide and sodium sulfite, followed by cooling the flask. To the above mixed solution, the reaction mixture containing 3-hydroxy-1-adamantane carboxylic acid was added while maintaining the solution temperature below 40° C., and the precipitated white crystals were collected by filtration and washed with water. Further, the resulting crystals were dried under reduced pressure at 40° C. for 8 hours to obtain white crystals of 3-hydroxy adamantane-1-carboxylic acid (30.0 g, yield: 85.3percent). A glass flask was equipped with a stirrer and a thermometer for use as a purification apparatus and was charged with sodium hydroxide (90.2 g), sodium sulfite (35.5 g) and ion exchanged water (812 g) to prepare a mixed solution of sodium hydroxide and sodium sulfite, followed by cooling the flask. To the above mixed solution, the reaction mixture containing 3-hydroxy-1-adamantane carboxylic acid was added while maintaining the solution temperature below 40° C., and the precipitated white crystals were collected by filtration and washed with water. Further, the resulting crystals were dried under reduced pressure at 40° C. for 8 hours to obtain white crystals of 3-hydroxy adamantane-1-carboxylic acid (30.0 g, yield: 85.3percent).

Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 98 - 118
[2] Patent: JP2016/84315, 2016, A, . Location in patent: Paragraph 0043-0045
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[4] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 10, p. 1680 - 1683[5] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 10, p. 2098 - 2102
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[12] Patent: US6344590, 2002, B1, . Location in patent: Example 4
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[16] Patent: WO2015/87262, 2015, A1, . Location in patent: Page/Page column 18; 19
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Reference: [1] Patent: JP5790430, 2015, B2, . Location in patent: Paragraph 0032; 0033; 0036
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  • [ 42711-75-1 ]
Reference: [1] Supramolecular Chemistry, 2017, vol. 29, # 2, p. 120 - 128
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 67 - 73
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  • [ 362003-83-6 ]
Reference: [1] Patent: US2009/170914, 2009, A1, . Location in patent: Page/Page column 18
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  • [ 1097119-35-1 ]
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