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Structure of 627-00-9 * Storage: {[proInfo.prStorage]}
* 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.
Reference：
[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998, vol. 37, # 10, p. 1037 - 1038
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. <B> 20, # 4, p. 340 - 342
[3] Annales de Chimie (Cachan, France), 1914, vol. <9>2, p. 332
[4] Chemische Berichte, 1925, vol. 58, p. 1013
[5] Bulletin de la Societe Chimique de France, 1886, vol. <2>45, p. 341[6] Chem. Zentralbl., 1898, vol. 69, # II, p. 273
[7] Patent: EP929544, 2004, B1, . Location in patent: Page 28
[8] Patent: WO2013/52394, 2013, A1, . Location in patent: Paragraph 00243
[9] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 548 - 557
[10] Journal of the American Chemical Society, 2014, vol. 136, # 50, p. 17662 - 17668
[11] Patent: EP3181554, 2017, A1, . Location in patent: Paragraph 0088
[12] Journal of the American Chemical Society, 2017, vol. 139, # 35, p. 12153 - 12156
[13] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2125 - 2130
[14] Chemistry and Biodiversity, 2018, vol. 15, # 9,
2
[ 4897-91-0 ]
[ 627-00-9 ]
Reference：
[1] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4975 - 4977
3
[ 36603-83-5 ]
[ 96-48-0 ]
[ 627-00-9 ]
[ 497-23-4 ]
Reference：
[1] Patent: KR2015/118287, 2015, A, . Location in patent: Paragraph 0154-0158
4
[ 96-48-0 ]
[ 627-00-9 ]
Reference：
[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998, vol. 37, # 10, p. 1037 - 1038
[2] Journal of the Chemical Society, 1955, p. 2371,2375
[3] Archiv der Pharmazie, 1961, vol. 294 /66, p. 488 - 498
5
[ 628-20-6 ]
[ 627-00-9 ]
Reference：
[1] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 8, p. 1781 - 1784
[2] Zeitschrift fuer Physikalische Chemie, Abteilung A: Chemische Thermodynamik, Kinetik, Elektrochemie, Eigenschaftslehre, 1935, vol. 172, p. 231[3] Zeitschrift fuer Physikalische Chemie, Abteilung A: Chemische Thermodynamik, Kinetik, Elektrochemie, Eigenschaftslehre, 1937, vol. 179, p. 41
[4] Acetylene Chemistry <New York 1949>S.121,
[5] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 162,182
6
[ 928-51-8 ]
[ 627-00-9 ]
Reference：
[1] Journal of the Chemical Society, 1952, p. 4492,4495
[2] Journal of the American Chemical Society, 1956, vol. 78, p. 2255,2256[3] Journal of Organic Chemistry, 1956, vol. 21, p. 883,885
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. <B> 20, # 4, p. 340 - 342
7
[ 3153-36-4 ]
[ 627-00-9 ]
Reference：
[1] Journal of the American Chemical Society, 1941, vol. 63, p. 2490
8
[ 188290-36-0 ]
[ 4635-59-0 ]
[ 627-00-9 ]
[ 43076-59-1 ]
Reference：
[1] Phosphorus and Sulfur and the Related Elements, 1987, vol. 33, p. 25 - 32
9
[ 1759-53-1 ]
[ 627-00-9 ]
Reference：
[1] American Chemical Journal, 1899, vol. 22, p. 334 Anm.
10
[ 616-45-5 ]
[ 625-38-7 ]
[ 627-00-9 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1952, vol. 576, p. 232
[2] Justus Liebigs Annalen der Chemie, 1952, vol. 576, p. 232
[3] Patent: DE887645, 1951, ,
11
[ 54634-49-0 ]
[ 625-38-7 ]
[ 627-00-9 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1952, vol. 576, p. 232
[2] Patent: DE887645, 1951, ,
12
[ 107-92-6 ]
[ 627-00-9 ]
Reference：
[1] Patent: US2302228, 1940, ,
13
[ 17219-57-7 ]
[ 627-00-9 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1961, p. 775 - 778[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1961, p. 838 - 842
14
[ 4635-59-0 ]
[ 627-00-9 ]
Reference：
[1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1975, p. 2129 - 2134
15
[ 3153-36-4 ]
[ 627-00-9 ]
[ 74-85-1 ]
Reference：
[1] Journal of Physical Chemistry, 1981, vol. 85, # 9, p. 1243 - 1245
Reference：
[1] Justus Liebigs Annalen der Chemie, 1901, vol. 319, p. 367
[2] Bulletin de la Societe Chimique de France, 1886, vol. <2>45, p. 341[3] Chem. Zentralbl., 1898, vol. 69, # II, p. 273
[4] Chemische Berichte, 1890, vol. 23, p. 1771[5] Chemische Berichte, 1909, vol. 42, p. 1252,Anm.2
18
[ 7647-01-0 ]
[ 3153-36-4 ]
[ 627-00-9 ]
Reference：
[1] Journal of the American Chemical Society, 1941, vol. 63, p. 2490
19
[ 56-23-5 ]
[ 7791-25-5 ]
[ 107-92-6 ]
[ 94-36-0 ]
[ 627-00-9 ]
[ 625-68-3 ]
[ 4170-24-5 ]
Reference：
[1] Journal of the American Chemical Society, 1940, vol. 62, p. 928
[2] Patent: US2302228, 1940, ,
20
[ 7782-50-5 ]
[ 107-92-6 ]
[ 627-00-9 ]
[ 625-68-3 ]
[ 4170-24-5 ]
Reference：
[1] Industrial and Engineering Chemistry, 1958, vol. 50, p. 1511
[2] Bulletin des Societes Chimiques Belges, 1952, vol. 61, p. 366,374
[3] Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 367,370
21
[ 627-00-9 ]
[ 75-50-3 ]
[ 6249-56-5 ]
Reference：
[1] Journal of Molecular Structure, 2001, vol. 563-564, p. 555 - 564
With hydrogenchloride; dodecatungstosilic acid; In water; at 20℃; under 760.051 Torr; for 2h;
86 g of gamma-butyrolactone was put into the flask, Keep stirring at room temperature under normal pressure. Add 5g of silicotungstic acid to the flask, Keep at room temperature and stirring at room temperature. Slowly add 200g of 20% hydrochloric acid, The reaction was stirred for 2 h. Sampling GC analysis, The gamma-butyrolactone residue is less than 1%, and the gamma-chlorobutyric acid content is 99% or more. The layer was allowed to stand still, and the lower layer product was collected, and the upper layer of water was repeatedly applied.
EXAMPLE 2a Allyl 4-chlorobutyrate To a mixture of 4-chlorobutyric acid (48 ml; 0.48 mole), allyl alcohol (200 ml) and hexane (1.2 l) p-toluenesulfonic acid (16.0 g; 0.08 mole) was added. The obtained mixture was heated for 5 hours at reflux temperature in such a way that water was simultaneously removed with Dean-Stark apparatus (Vogel's Textbook of Practical Organic Chemistry, Fourth Ed., Longman, London, 1978, p. 411). The mixture was then cooled to room temperature and shaken with 7% aqueous sodium hydrogencarbonate solution (2*500 ml). The obtained solution was dried with magnesium sulfate and after the filtration of the drying agent hexane was evaporated. The crude residue was distilled under reduced pressure 10 mbar at the temperature of 95 C. and the title compound (61.2 g; 79%) was obtained in the form of a colourless oil. IR (film): numax (cm-1): 2964, 1738, 1733, 1198, 1176, 1146, 909. MS (M+): 162. 1H-NMR (300 MHz, TMS, CDCl3): delta: 2.10 (2H, m), 2.54 (2H, t, J=8 Hz), 3.61 (2H, t, J=8 Hz), 4.58 (2H, dt, J=4 Hz, 1.4 Hz), 5.26 (1H, dq, J=10 Hz, 1.4 Hz), 5.33 (1H, dq, J=17 Hz, 1.4 Hz), 5.91 (1H, m).
1-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrrolidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
26%
With NaH; CDI; In dichloromethane; acetonitrile; mineral oil;
EXAMPLE 8 Preparation of 1-(1,2,3,4-tetrahydro-1-naphtyl)-pyrrolidin-2-one (ST 748) CDI (6.61 g. 40.75 mmoles) and, after 1 hour, 1,2,3,4-tetrahydro-1-naphtylamine (5 g, 33.96 mmoles) were added to 4-chlorobutyric acid (4.16 g, 33.96 mmoles) in CH2 Cl2 (200 mL) under stirring. The resulting solution was kept at room temperature for 40 hours, then washed with 1N HCl, NaHCO3 (saturated solution), H2 O, NaCl (saturated solution) and dried over anhydrous Na2 SO4. The solvent was evaporated and the residue taken up with CHCl3. Upon addition of Et2 O under stirring a precipitate was obtained consisting of 4.5 g (17.87 mmoles) of N-(4-chloro-butyroyl)-1,2,3,4,-tetrahydro-1-naphtylamine (silica gel TLC; Eluant EtOAc-Hexane (1:1), RF=0.7) which was dissolved in CH3 CN (100 mL). To the mixture, 80% NaH in mineral oil (804 mg, 26.8 mmoles) was added in two portions, the second portion after some hours following the first one. The mixture was then kept at room temperature under stirring for 2 days. The mixture was then filtered, the filtrate evaporated and the residue chromatographed on silica gel using EtOAc-Hexane (1:1) as eluant. 1.93 g of the title compound were obtained. Last step yield=50%, overall yield 26%. M.P.=103-104 C. Silica gel TLC; Eluant EtOAc-HEXANE (1:1). RF=0.32.
(m) Preparation of gamma-phthalimidobutyric acid 3 g of 4-chlorobutyric acid is reacted with 4.5 g (molar ratio 1/1) of potassium phthalimide in 60 ml of DMF with stirring and at room temperature. The reaction mixture is then treated after 2 hours by adding water and filtering the precipitate so formed. After crystallization from ethanol, 4.6 g of phthalimidobutyric acid is obtained with 80% yield.
80%
In water; N,N-dimethyl-formamide;
(m) Preparation of gamma-phthalimidobutyric acid 3 g of 4-chlorobutyric acid is reacted with 4.5 g (molar ratio 1/1) of potassium phthalimide in 60 ml of DMF with stirring and at room temperature. The reaction mixture is then treated after 2 hours by adding water and filtering the precipitate so formed. After crystallization from ethanol, 4.6 g of phthalimido butyric acid is obtained with 80 % yield.
C. A solution of lithium amide in liquid ammonia is prepared by the addition of lithium metal (2 mmoles) to liquid ammonia containing a trace amount of ferrous sulfate. To this solution is added 4-chlorobutyric acid (1 mmole) and p-(n-octyl)benzylacetylene (1 mmole, prepared as described in paragraph B of this example). After a suitable time at refluxing liquid ammonia temperatures, the ammonia is removed by evaporation and the residue dissolved in 10% sodium hydroxide solution. After extraction with ether, the aqueous layer is acidified to a pH of 2-3 with concentrated hydrochloric acid, and extracted with methylene chloride. The methylene chloride layer is separated and the solvent removed by evaporation to give a residue. This residue is purified either by column chromatography or molecular distillation under reduced pressure to afford the desired title product, 7-[p-(n-octyl)phenyl]hept-5-ynoic acid.
PART A 2-(4-Chlorobutyryl)-1-naphthol A mixture of 1-naphthol (15.14 g, 0.105 mole), 4-chlorobutyric acid (9.90 mL, 0.100 mole), and boron trifluoride etherate (75 mL) was heated on a steam bath for 4 hours. The mixture was then treated slowly with 100 mL of water, and heating continued for 30 minutes. The mixture was poured into water, stirred, and the solution decanted. The residue was triturated with water, then crystallized from ethanol to provide the title compound (9.50 g, 38%) as a pale green solid, mp 73-79.
500 g of polyphosphoric acid and 69 g of veratrol are added to a 1 liter round-bottomed flask. To this are added 61 g of 4-chlorobutyric acid in one portion, the temperature rising steadily to 55 C. After 1 hours, the entire mixture is poured on to ice. The mixture is then extracted with a mixture of ether/methylene chloride (3:1). The organic extracts are extracted with water, then with a saturated sodium bicarbonate solution and finally again with water, dried over magnesium sulphate and evaporated in vacuo. The residual crystal mass is recrystallized from ether. There are obtained 62.9 g of 3,4-dimethoxy-gamma-chlorobutyrophenone of melting point 91-92 C.
3-(β-Acetoxyethyl)-7-hydroxy-1,2,4,5-tetrahydro-3H,3-benzazepine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In N-methyl-acetamide;
EXAMPLE 46 3-(beta-Acetoxyethyl)-7-hydroxy-1,2,4,5-tetrahydro-3H,3-benzazepine 7-Hydroxy-1,2,4,5-tetrahydro-3H,3-benzazepine (13.98 gm., 0.0855 m) and triethylamine (17.9 gm., 0.18 m) were dissolved in dimethylformamide (60 ml.) and the solution was heated and stirred to 100. 2-Chloroethylacetate (22 gm., 0.18 m) was added dropwise during 5 minutes. After 5 hours at 100 the reaction was cooled and diluted with ethyl acetate (300 ml.). The ethyl acetate extract was washed with water and dried over magnesium sulfate. Evaporation of the solvent in vacuo afforded an oil. The oil was extracted with hot diisopropyl ether and the resultant solution was cooled to -70 C. A gum precipitated and the supernatant solvent was decanted from it. The solution precipitated a small quantity (1.3 gm.) of the required ester. The solvent was evaporated in vacuo and the residue was combined with the gum from above and chromatogrammed on silica gel. Elution with benzenemethanol (9:1) afforded were converted to the oxalate salt which was recrystallized from methanol:ether (2:1) m.p. 161-163. Anal. Calc. for C16 H21 NO7: C. 56.63; H, 6.24; N, 4.13. Found: C, 56.76; H, 6.25; N, 4.38.
1-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrrolidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
26%
With NaH; CDI; In diethyl ether; dichloromethane; acetonitrile; mineral oil;
Example 8 Preparation of 1-(1,2,3,4-tetrahydro-1-naphtyl)-pyrrolidin-2-one (ST 748) CDI (6.61 g, 40.75 mmoles) and, after 1 hour, 1,2,3,4-tetrahydro-1-naphtylamine (5 g, 33.96 mmoles) were added to 4-chlorobutyric acid (4.16 g, 33.96 mmoles) in CH2Cl2 (200 mL) under stirring. The resulting solution was kept at room temperature for 40 hours, then washed with 1N HCl, NaHCO3 (saturated solution), H2O, NaCl (saturated solution) and dried over anhydrous Na2SO4. The solvent was evaporated and the residue taken up with CHCl3. Upon addition of Et2O under stirring a precipitate was obtained consisting of 4.5 g (17.87 mmoles) of N-(4-chloro-butyroyl)-1,2,3,4,-tetrahydro-1-naphtylamine (silica gel TLC; Eluant EtOAc-Hexane (1:1), RF = 0.7) which was dissolved in CH3CN (100 mL). To the mixture, 80 % NaH in mineral oil (804 mg, 26.8 mmoles) was added in two portions, the second portion after some hours following the first one. The mixture was then kept at room temperature under stirring for 2 days. The mixture was then filtered, the filtrate evaporated and the residue chromatographed on silica gel using EtOAc-Hexane (1:1) as eluant. 1.93 g of the title compound were obtained. Last step yield = 50 %, overall yield 26%. M.P. = 103-104C Silica gel TLC; Eluant EtOAc-HEXANE (1:1) RF = 0. 32
Example 11 Preparation of 4-(4-tert-pentylphenoxy)-gamma-butyric acid 94% pure acid (2.8% of residual phenol) was prepared in an analogous manner in a yield of 92.6% of theory from <strong>[627-00-9]gamma-chlorobutyric acid</strong> and 4-tert-pentylphenol.
With sodium iodide; triethylamine; In N-methyl-acetamide; water;
Example 1-1-3 Synthesis in another route of 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-(methacryloyloxy)butyrate A mixture of 4.17 g of triethylamine and 10 g of dimethylformamide was added dropwise to a mixture of 3.73 g of methacrylic acid, 10.0 g of the 4-chlorobutyrate obtained in Example 1-1-1, 0.71 g of sodium iodide, and 40 g of dimethylformamide at 60-70 C. The mixture was stirred at the temperature for 8 hours. 100 ml of water was added below 30 C. This was followed by ordinary work-up and recrystallization from toluene and n-hexane, obtaining 10.9 g of the target compound (yield 73%). The spectroscopic data of this compound were exactly identical with those of the compound synthesised in Example 1-1-2.
Example 1-1-2 Synthesis in one route of 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-(methacryloyloxy)butyrate A mixture of 10.0 g of the 4-chlorobutyrate obtained in Example 1-1-1 and 30 g of dimethylformamide was added dropwise to a mixture of 4.69 g of sodium methacrylate, 0.71 g of sodium iodide and 20 g of dimethylformamide at 60-70 C. The mixture was stirred at the temperature for 8 hours. 100 ml of water was added below 30 C. This was followed by ordinary work-up and silica gel chromatography purification, obtaining 8.12 g of the target compound (yield 70%). IR (thin film): nu=2983, 2958, 1785, 1737, 1718, 1637, 1436, 1367, 1336, 1321, 1297, 1201, 1157, 1118, 1087, 1014 cm-1 1H-NMR (600 MHz in CDCl3): delta=1.66 (1H, dd), 1.93 (3H, m), 2.01 (2H, q), 2.04 (1H, d), 2.42 (2H, dt), 2.76 (1H, m), 2.82 (1H, dd), 3.08 (1H, dd), 3.31 (1H, t-like), 3.72 (3H, s), 4.18 (2H, t), 4.59 (1H, d), 5.25 (1H, s), 5.56 (1H, m), 6.08 (1H, s) ppm
EXAMPLE 21 5-chloro-thiophene-2-carboxylic acid-N-({1-[4-(2-oxo-pyrrolidin-1-yl)-phenyl]-1H-imidazol-4-yl}-methyl)-amide 109 mul (1.10 mmol) 4-chloro-butyric acid in 2 ml DMF are combined with 132 mul (1.20 mmol) NMM and 353 mg (1.10 mmol) TBTU and stirred for 5 min at ambient temperature. Then 333 mg (1.00 mmol) 5-chloro-thiophene-2-carboxylic acid-N-({1-[4-amino-phenyl]-1H-imidazol-4-yl}-methyl)-amide are added and the mixture is stirred for 16 h at ambient temperature. Then 96 mg (2.0 mmol) 50% sodium hydride are added batchwise and the mixture is stirred for 45 min at ambient temperature and for 45 min at 70 C., another 48 mg (1.0 mmol) 50% sodium hydride are added and the mixture is stirred for another 1.5 h at 70 C. Then it is poured into ice water, suction filtered and washed with water. After drying the filter cake is purified by chromatography on silica gel (eluding gradient: dichloromethane/(methanol/conc. ammonia 19:1)=20:0?19:1). Yield: 250 mg (62%) Rf value: 0.30 (silica gel; ethyl acetate/ethanol=9:1+0.5% conc. ammonia solution) C19H17ClN4O2S (400.88) Mass spectrum: (M+H)+=401/403 (chlorine isotopes)
Example 71-(4-carboxylbutyl)imidazolium chloride; A mixture of 1-methylimidazole (0.077 mol) and <strong>[627-00-9]4-chlorobutanoic acid</strong> (0.05 mol) were heated with stirring at 70 C. overnight. On completion ether was added. The solid-oil was washed with ether (50 mL×3). The slightly yellow sticky oil was dried under vacuum overnight.
With triethylamine; In tetrahydrofuran; at 0℃; for 1h;
General procedure: Two twenty one milligram of 3-aminocoumarin IIa20 or 3-amino-6,7-dimethoxycoumarin II21 (1.0 mmol) and 607 mg of triethylamine (0.84 mL; 6.0 mmol) were dissolved in 8 mL of anhydrous THF. A solution of 1.0 mmol of the appropriate ?-chloroacyl chloride (n = 1-3; see Scheme 3) in 2 mL of anhydrous THF was dropped through a dropping funnel under vigorous magnetic stirring in the reaction flask kept in ice-cold water. After 1 h the suspension was filtered and the solution evaporated to dryness, yielding ?-chloroamides VIIa-d in quantitative yield. Crude VIIa-d were reacted with N-methylbenzylamine in the above reported conditions A to give final compounds 9-12. Compound 10 was crystallized as hydrochloride.
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere;
General procedure: The mixture of cholesterol (2.0g, 5mmol), 2-chloroacetic acidor <strong>[627-00-9]4-chlorobutanoic acid</strong>( 6mmol), N, N?-dicyclohexylcarbodiimide (1.24g, 6mmol) and 4-dimethylaminopyridine (0.08g, 0.65mmol) wasstirred at room temperature in 20mL of dry CH2Cl2 overnight.Some white precipitation was formed and TLCdetection indicated the disappearance of startingmaterials. Then theprecipitation was filtered and 20 mL of distilled waterwas addedinto the solution with vigorous stirring at room temperature. The organic layer was separated out and evaporated to dryness by rota-vapor.The residue was further purified by the operation of recrystallization in CH2Cl2/MeOH. The compound 2a and 2b were obtainedas white solid inyield of 90% and 88%, respectively
88%
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;
General procedure: According to the literature(Tetrahedron Lett., 2015, 56, 866-870), the mixture of cholesterol (2.0g, 5mmol), 2-chloroacetic acid or <strong>[627-00-9]4-chlorobutanoic acid</strong> ( 6mmol), N, N?-dicyclohexylcarbodiimide (1.24g,6mmol) and 4-dimethylaminopyridine (0.08g, 0.65mmol) was stirred at room temperature in 20mL of dry CH2Cl2 overnight.Some white precipitation was formed and TLC detection indicated the disappearance of starting materials. Then the precipitationwas filtered and 20 mLof distilled water was added into the solution with vigorous stirringat room temperature. The organic layer was separated out and evaporated to dryness by rota-vapor. The residue was further purified by theoperation of recrystallization in CH2Cl2/MeOH. The compounds 5a and 5bwere obtained as white solid in yields of 90% and 88%, respectively.Compound 5a: 1HNMR (400 MHz, CDCl3) deltappm: 0.68~2.35 (m, 43H of cholesterol), 4.66 (s, 2H, ClCH2),4.75 (bs, 1H, OCH on cholesterol), 5.39 (s, 1H, CH=C on cholesterol); MS m/z (%): 464.4 (M+, 100). Compound 5b: 1H NMR (400 MHz, CDCl3) deltappm: 0.68~2.34 (m, 45H of cholesterol and CH2 on butyl), 2.51(t, 2H, J=7.2Hz, CH2C=O),4.08 (t, 2H, J=6.0Hz, ClCH2),4.64 (m, 1H, OCH on cholesterol), 5.38 (m, 1H, CH=C on cholesterol); MS m/z (%): 491.6 (M+, 100).
(S)-4-(5-(2-(1H-imidazo[4,5-b]pyrazin-2-yl)propan-2-yl)-9-fluoro-5H-chromeno[2,3-b]pyridin-2-yl)aniline[ No CAS ]
(S)-N-(4-(5-(2-(1H-imidazo[4,5-b]pyrazin-2-yl)propan-2-yl)-9-fluoro-5H-chromeno[2,3-b]pyridin-2-yl)phenyl)-4-chlorobutanamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 4h;
Step 1 : To a solution of the title compound-derived from the Example 22, (S)-4- (5-(2-(lH-imidazo[4,5-b]pyrazin-2-yl)propan-2-yl)-9-fluoro-5H-chromeno[2,3-b]pyridin- 2-yl)aniline (50 mg, 0.111 mmol), in DMF was added <strong>[627-00-9]4-chlorobutanoic acid</strong> (13.54 mg, 0.111 mmol), BOP (98 mg, 0.221 mmol), and DIEA (0.058 mL, 0.332 mmol). The mixture was stirred at r.t for 4h, and then was diluted with AcOEt (40 mL), washed with saturated NaHC03 (2x30 mL), dried(Na2S04), and concentrated under vacuo to give the crude product which was used for the next step without further purification. LC-MS, 558 (M+l).
General procedure: A mixture of 1.5 g (0.0049 mol) of triphenylarsine and 0.47 g (0.0049 mol) of chloroacetic acid was melt-fused at 100C during 25 h. The reaction mixture was then treated with water, and the unreacted triphenylarsine was filtered off. The white crystalline product obtained after distillation the solvent off in vacuum was washed several times with diethyl ether, recrystallized from a mixture of anhydrous ethanol and diethyl ether, and dried in vacuum.
In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere;
7.7 4-(Acetylthio)butanoic acid (1c) The method of Hogg et al. was adapted [43] . Potassium thioacetate (1.0 g, 8.8 mmol) was added portionwise to a solution of 4-chlorobutyric acid (1.0 g, 8.2 mmol) in dry DMF (5 mL) at room temperature. The reaction mixture was stirred under argon for 2 h then the organic solvent was removed under reduced pressure. The residue was taken up in ethyl acetate (50 mL) and washed with HCl (5%, 2 * 50 mL) and water (3 * 50 mL). The organic phase was dried (Na2SO4), filtered and evaporated to give 4-(acetylthio)butanoic acid (1c) as a dark oil (0.78 g, 59%). 1H NMR (400 MHz, CDCl3): delta 2.91 (2H, t, J = 7.1 Hz, CH2S), 2.42 (2H, t, J = 7.4 Hz, CH2CO), 2.32 (3H, s, CH3), 1.91 (2H, quintet, J = 7.2 Hz, CH2CH2CH2). 13C NMR (100 MHz, CDCl3): delta 195.6 (SCO), 178.3 (CO2), 32.5 (CH2CO), 30.6 (CH2S), 28.2 (CH3), 24.5 (CH2CH2CH2). The NMR spectra are in agreement with the literature
In a container (internal capacity: 100 ml) equipped with a stirrer, a condenser tube, and a burette, 10 g (21 mmol) of the above XBisN-1 of (Synthesis Example 15) and 14.8 g (107 mmol) of potassium carbonate were charged to 50 ml of dimethylformamide, and 6.56 g (54 mmol) of acetic acid-2-chloroethyl was further added thereto. The reaction solution was stirred at 90 C. for 12 hours to perform reaction. Next, the reaction solution was cooled in an ice bath to precipitate a crystal, which was separated by filtration. Subsequently, 40 g of the crystal, 40 g of methanol, 100 g of THF, and 24% aqueous sodium hydroxide solution were charged to a container (internal capacity: 100 ml) equipped with a stirrer, a condenser tube, and a burette. The reaction solution was stirred for 4 hours under reflux to perform reaction. Subsequently, the reaction solution was cooled in an ice bath and concentrated. The precipitated solid matter was filtered, dried, and then separated and purified by column chromatography to obtain 5.9 g of the objective compound represented by the following formula (7?).The obtained compound was subjected to NMR measurement under the above measurement conditions. The following peaks were found, and the compound was confirmed to have a chemical structure of the following formula (7?).delta (ppm) 8.6 (2H, O-H), 7.2-7.8 (19H, Ph-H), 6.7 (1H, C-H), 4.0 (4H, -O-CH2-), 3.8 (4H, -CH2-OH)The compound had the thermal decomposition temperature of 375 C., the glass transition point of 132 C., and the melting point of 256 C. and could thereby be confirmed to have high heat resistance.
With hydrogenchloride; In water; for 5h;Schlenk technique; Reflux;
To a mixture of 1,2-diaminobenzene, 4 (0.5g, 4.6mmol) and <strong>[627-00-9]4-chlorobutanoic acid</strong>,5 (0.86g, 7mmol) in a schlenk tube was added 5N HCl solution (25mL) and heated to boil for 5h. The reaction mixture was then cooled and added to water (25mL). The precipitate obtained was filtered and vacuum dried to give a white solid (1.25g, 56%) which was used in the next step without further purification.
56%
With hydrogenchloride; In water; for 5h;Schlenk technique; Heating;
2-(3-Chloro-propyl)-1H-benzoimidazole, D (FIG. 11): To a mixture of 1,2-diaminobenzene,4 (FIG. 10) (0.5 g, 4.6 mmol) and <strong>[627-00-9]4-chlorobutanoic acid</strong>, 5 (FIG. 10) (0.86 g, 7 mmol) in a schlenk tube was added 5N HCl solution (25 mL) and heated to boil for 5 h. The reaction mixture was then cooled and added to water (25 mL). The precipitate obtained was filtered and vacuum dried to give a white solid (1.25 g, 56%) which was used in the next step without further purification.
With palladium on activated carbon; at 130℃; under 760.051 Torr; for 4h;
3 g of Cl-GBL and the solvent of Table 11 (30 g) and the catalyst were charged into the reactor, respectively, and the reaction was allowed to proceed to evaluate the degree of dechlorination of Cl-GBL. The reaction was allowed to proceed at atmospheric pressure (1 atm), and the product was partially recovered to analyze the components. The results are shown in Table 11 below.
1-(3'-carboxylpropyl)-3-methylimidazolium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
at 70℃;
A mixture of 1 -methylimidazole (0.077 mol) and <strong>[627-00-9]4-chlorobutanoic acid</strong> (0.05 mol) were heated with stirring at 70C overnight. On completion ether was added. The solid-oil was washed with ether (50ml_x3). The slighty yellow sticky oil was dried under vacuum overnight.
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