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Structure of 88-10-8 * 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] Journal of Organic Chemistry, 1948, vol. 13, p. 144,149
2
[ 109-01-3 ]
[ 88-10-8 ]
[ 90-89-1 ]
Reference：
[1] Journal of Organic Chemistry, 1948, vol. 13, p. 144,149
3
[ 32315-10-9 ]
[ 109-89-7 ]
[ 88-10-8 ]
Reference：
[1] Research on Chemical Intermediates, 2014, vol. 40, # 2, p. 787 - 800
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6875 - 6884
[3] Chemical Biology and Drug Design, 2016, vol. 87, # 6, p. 946 - 957
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 1030 - 1041
Reference：
[1] Bulletin de la Societe Chimique de France, 1904, vol. <3> 31, p. 691
[2] Journal of the Chemical Society, 1957, p. 3165,3171
[3] Collection of Czechoslovak Chemical Communications, 1953, vol. 18, p. 870,874[4] Chem.Abstr., 1953, p. 12302
[5] Journal of the Chemical Society, 1947, p. 313[6] Journal of the Chemical Society, 1956, p. 5041
[7] Chemicke Listy, 1952, vol. 46, p. 762,764[8] Collection of Czechoslovak Chemical Communications, 1953, vol. 18, p. 870,876[9] Chem.Abstr., 1953, p. 12302
[10] Helvetica Chimica Acta, 1961, vol. 44, p. 1806 - 1809
[11] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, p. 2430 - 2433[12] Zhurnal Obshchei Khimii, 1967, vol. 37, p. 2554 - 2558
[13] Russian Journal of Applied Chemistry, 1995, vol. 68, # 4.2, p. 589 - 593[14] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1995, vol. 68, # 4, p. 675 - 679
[15] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 4, p. 978 - 983
9
[ 3553-80-8 ]
[ 88-10-8 ]
Reference：
[1] Synthetic Communications, 1987, vol. 17, # 16, p. 1887 - 1892
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3207 - 3212
10
[ 97-77-8 ]
[ 88-10-8 ]
[ 88-11-9 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 4.2, p. 819 - 822[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, # 4, p. 909 - 913
[3] J. Gen. Chem. USSR (Engl. Transl.), 1988, vol. 58, # 7, p. 1328 - 1331[4] Zhurnal Obshchei Khimii, 1988, vol. 58, # 7, p. 1489 - 1493
Reference：
[1] Chemical and Pharmaceutical Bulletin, 2002, vol. 50, # 12, p. 1584 - 1588
19
[ 91-21-4 ]
[ 32315-10-9 ]
[ 121-44-8 ]
[ 88-10-8 ]
[ 199480-42-7 ]
Reference：
[1] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7289 - 7297
20
[ 55441-26-4 ]
[ 88-10-8 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1882, vol. 214, p. 259
21
[ 75-44-5 ]
[ 121-44-8 ]
[ 88-10-8 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1969, # 1, p. 98 - 105[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1969, # 1, p. 112 - 119
136 g ( 1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (= 1 27 ml. 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask lltted with air condenser which is placed over a magnetic stirrer. To this, 121 g ( 167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction m ixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-diethyl m-toluamide (DEET) is obtained by vacuum disti l lation of organic layer wh ich is the product. Purity of the compound is analyzed using GC-MS which is more than 99.5percent. The yield of the product is 186 g (97.5percent).
97.5%
at 20℃; for 0.333333 h;
Example 2 Preparation of N,N-Diethyl m-Toluamide (DEET) [0095] 136 g (1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (=127 ml, 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask fitted with air condenser which is placed over a magnetic stirrer. To this, 121 g (167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction mixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-Diethyl m-toluamide (DEET) is obtained by vacuum distillation of organic layer which is the product. [0096] Purity of the compound is analyzed using GC-MS which is more than 99.5percent. The yield of the product is 186 g (97.5percent).
Reference：
[1] Angewandte Chemie - International Edition, 2014, vol. 53, # 34, p. 9026 - 9029[2] Angew. Chem., 2014, vol. 126, # 34, p. 9172 - 9175,4
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 4, p. 440 - 446
25
[ 54-21-7 ]
[ 88-10-8 ]
[ 19311-91-2 ]
Reference：
[1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 6, p. 1115 - 1119[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 6, p. 1287 - 1291
26
[ 88-10-8 ]
[ 108-95-2 ]
[ 65009-00-9 ]
[ 79119-31-6 ]
[ 19311-91-2 ]
Reference：
[1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 6, p. 1115 - 1119[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 6, p. 1287 - 1291
27
[ 88-10-8 ]
[ 108-95-2 ]
[ 65009-00-9 ]
[ 19311-91-2 ]
[ 82819-71-4 ]
Reference：
[1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 6, p. 1115 - 1119[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 6, p. 1287 - 1291
28
[ 88-10-8 ]
[ 73540-75-7 ]
Yield
Reaction Conditions
Operation in experiment
68%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 24 h; Reflux
A representative procedure: Into a 25 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.18 g, 5 mol percent) and 10 mL of 4-ethoxycarbonylphenylzinc bromide chloride (0.5 M in THF, 5.0 mmol). Next, diethylcarbamoyl chloride (0.54 g, 4.0 mmol) was added via a syringe. The resulting mixture was stirred at refluxing temperature for 24 h. Cooled down to room temperature and quenched with saturated NH4Cl solution, then extracted with ethyl acetate (10 mL .x. 3). Washed with saturated Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (20percent ethyl acetate/80percent heptane) afforded ethyl 4-(diethylcarbamoyl)benzoate (1c, 0.70 g) as a yellow oil in 70percent isolated yield.
With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 16h;
General procedure: To a solution of the phenol derivative (1 eq.) indichloromethane (0.1 M) was added the carbamoyl chloride (1.5 eq.). Theresulting solution was stirred at 0 oC for 10 min, after whichtriethylamine (1.5 eq.) and 4-dimethylaminopyridine (0.1 eq.) were added andthe reaction mixture allowed to warm up to room temperature and left stirringfor 16 hours. The mixture was washed with 1 M HCl (3×), and extracted withdichloromethane (2×). The combined organic layers were washed with distilled water (2×) and brine, dried (MgSO4),filtered and the solvent evaporated in vacuo to afford the pure carbamoylated phenols directly orafter flash column chromatography.
1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethyl-carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
21.3%
With pyridine; for 2h;Heating / reflux;
Production of 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethyl-carbamate (Compound 97) Compound 6 (150 mg) was dissolved in pyridine (1 mL), and diethylcarbamoyl chloride (55 mg) was added to the solution, followed by stirring under reflux for 2 hours. After completion of reaction, methanol was added to the reaction mixture, followed by stirring for 30 minutes. The solvent was evaporated to dryness, and the residue was extracted with chloroform and purified water. The organic layer was dried over sodium sulfate anhydrate, and the solvent was evaporated to dryness. The residue was recrystallized from ethyl acetate, to thereby yield the target product (yield: 40.6 mg, 21.3%). Yellow powder MS (ESI,m/z):470(M+H)+ 1H-NMR(CDCl3)delta:7.37(1H,s),7.23(1H,d,J=4.4), 7.13(1H,dd,J=2.2,8.5),7.04(1H,d,J=2.2),6.87(1H,d,J=8.5), 6.05(1H,d,J=4.4),4.93-4.97(1H,m),3.74(3H,s),3.90(3H,s), 3.48-3.54(2H,m),3.30-3.36(6H,m),2.01-2.08(2H,m), 1.83-1.91(2H,m),1.14(6H,t,J=7.1)
With pyridine; triethylamine; In acetonitrile; at 50℃; for 6h;
Example 1-2: Synthesis of Exemplified compound (1) The compound was synthesized in accordance with following reaction scheme. [] Into 50 mL of acetonitrile were dissolved 9.75 g (0.050 mol) of <strong>[3279-07-0]4-t-butyl-2-nitrophenol</strong> and 8.13 g (0.060 mol) of N,N-diethylcarbamoyl chloride, and then, to the resultant solution, were added 8.4 mL of triethylamine and 1.0 mL of pyridine. The resultant solution was stirred at 50 C for 6 hours. To the reaction solution were added ethyl acetate and water, to extract the reaction product. The organic phase was washed with each of a 0.1N potassium carbonate aqueous solution, diluted hydrochloric acid, and saturated brine, followed by drying over anhydrous magnesium sulfate. The result was filtered and then the solvent was distilled off under reduced pressure. The remaining product was purified by silica gel chromatography, using a mixed solvent of ethyl acetate and hexane as an eluent, to yield 14.3 g (0.043 mol) of Exemplified compound (2A), as a light yellow oil substance. Yield: 86.6%.
N,N-Diethylcarbamoyl chloride(80 muL, 0.63mmol) was added to a solution of 5-chloro-2-hydroxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide(compound of Example 1(1); 0.20g, 0.52mmol) in pyridine(3mL), and the mixture was stirred at 60°C for 4 hours. The reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was crystallized by isopropyl ether/n-hexane to give the title compound(231.2mg, 92.1percent) as a white crystal.1H-NMR(CDCl3): delta 1.16(3H, t, J=7.2Hz), 1.20(3H, t, J=7.2Hz), 3.41(2H, q, J=7.2Hz), 3.45(2H, q, J=7.2Hz), 7.05(1H, d, J=9.0Hz), 7.44(1H, dd, J=9.0, 2.7Hz), 7.62(1H, s),7.70(1H, d, J=2.7Hz), 8.09(2H, s), 9.25(1H, s).
4.4.2. A solution of alcohol 1-OH8i,19b (500 mg, 2.69 mmol,1.0 equiv) in THF (7.0 mL) was added dropwise to a solution ofNaH (77.3 mg, 3.22 mmol, 1.2 equiv) in THF (1.8 mL) at 0 C. Theresulting mixture was allowed to stir at room temperature for10 min after which a solution of N,N-diethyl carbamoyl chloride(437 mg, 3.22 mmol, 1.2 equiv) in THF (2.9 mL) was added to it at0 C. The resulting solution was allowed to warm to room temperatureand stirred at room temperature for 15 h. The reactionmixture was then quenched with H2O (1.0 mL) at 0 C andtransferred to a separatory funnel. The aqueous and organic layerswere separated and the organic layer was extracted with 1.0 Maqueous KOH solution (120 mL), H2O (120 mL), and brine(120 mL). The organic layer was dried over MgSO4, filtered,concentrated, and chromatographed on a silica gel column using90/10 hexanes/EtOAc (Rf0.24 in 90% hexanes/10% ethyl acetate).The product 1-OCONEt2 was obtained as a clear viscous oil(471 mg, 61% yield). 1H NMR (CDCl3): d 7.32e7.26 (multiple peaks,3H), 7.21e7.14 (multiple peaks, 2H), 7.08e7.03 (multiple peaks,2H), 6.98 (d, J8.1 Hz, 2H), 3.30 (q, J7.2 Hz, 2H), 3.19 (q,J7.2 Hz, 2H), 1.11 (t, J7.2 Hz, 3H), 1.06 (t, J7.2 Hz, 3H). 13C{1H}NMR (CDCl3): d 157.6, 153.4, 147.9, 143.1, 129.4, 126.1, 124.3, 124.2,122.6, 121.2, 117.3, 42.2, 41.7, 13.8, 13.2. IR (neat): 2975, 1717, 1587,1488, 1472, 1417, 1254, 1204, 1184, 1104, 1074, 879, 783, 745,690 cm1. HRMS calcd for C17H19O3NNa 308.1263; found:308.1271.
With pyridine; for 5.1h;Heating / reflux;
2-Phenoxy phenyl 51 (0.95 g, 5.1 mmol) was dissolved in pyridine under a N2 atmosphere. Diethyl carbamyl chloride (0.65 mL, 5.1 mmol) was added to solution over 5 min after which the solution is heated at reflux for 5 h. The pyridine is removed by rotary evaporation and the crude product dissolved in ether. The ether solution was washed with 0.5 M aqueous KHSO4 followed by brine, and dried (Na2SO4) to give 0.60 g of crude 2-phenoxyphenyl diethyl carbonate 52. Flash chromatography (10% EtOAc in hexanes) further purified the product.MS (chemical ionization) m/z calcd for [M+1] 286.14, found 286.1H NMR (300 MHz, DMSO-d6) delta: 7.25 (m, 5H), 7.09 (m, 2H), 6.80 (m, 2H), 3.5-3.0 (m), 0.9 (p, 6H).
Step 2 5,6-Dimethyl-2-pyridinecarbonitrile To a slurry of N-oxide from Step 1 (8.7 g) in CH2 Cl2 (125 mL) at r.t. was added trimethylsilylcyanide (9.9 mL, 74.2 mmol). After stirring for 15 minutes, N,N-diethylcarbamoyl chloride (9.4 mL, 74.2 mmol) was added and the resulting mixture was allowed to stir at r.t. for 2.5 days. The reaction was quenched by careful addition of 10% aq. K2 CO3, stirred 15 minutes, and extracted (3*) with CH2 Cl2. The organic layer was washed with aq. K2 CO3, brine, and dried over Na2 SO4 /K2 CO3. Evaporation of the solvent and purification of the residue by flash chromatography (25% to 50% Et2 O in hexanes) yielded 4.13 g of the title compound. 1 H NMR (CD3 COCD3): delta 7.73 (1H, d), 7.62 (1H, d), 2.51 (3H, s), 2.39 (3H, s).
3-(diethylaminocarbonyloxy)-1,2-dimethyl-4(1H)-pyridinone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; triethylamine; In methanol; dichloromethane; ethyl acetate; acetonitrile;
EXAMPLE 4 With stirring, 0.56 ml of triethylamine is added at room temperature to a suspension of 0.556 g of <strong>[30652-11-0]3-hydroxy-1,2-dimethyl-4(1H)-pyridinone</strong> in 40 ml of acetonitrile and 40 ml of methylene chloride, followed by the addition of 0.76 ml of diethylcarbamoyl chloride. The suspension still remains intact after 60 minutes and thin-layer chromatography shows that no reaction has taken place. Then 20 ml of pyridine are added to the mixture, which turns yellowish in colour. After a further 60 minutes the onset of reaction can be observed. This reaction is brought to completion by stirring for 16 hours. The volatile constituents are removed by evaporation under reduced pressure. The residue is dried under a high vacuum, then dissolved in methanol, and the solution is treated with activated carbon, filtered and concentrated by evaporation. The filtrate is taken up in 100 ml of ethyl acetate, whereupon a product crystallises. A furthher crystalline product can be obtained by working up the mother liquor. The two products are combined and dissolved in methylene chloride. The solution is washed twice with water and the organic phase is concentrated by evaporation. The residue is crystallized from ethyl acetate, affording 3-(diethylaminocarbonyloxy)-1,2-dimethyl-4(1H)-pyridinone with a melting point of 135-137 C.
N,N-diethylcarbamyl-4,5-dibromo-1H-1,2,3-triazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2.4 g (82%)
In tetrahydrofuran;
EXAMPLE 4 1(2 or 3)-N,N-Diethylcarbamyl-<strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong> STR13 To a suspension of 213 milligrams (mg) (8.89 mmoles) of sodium hydride in 20 ml of anhydrous tetrahydrofuran was added 2 g (8.89 mmoles) of <strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong>. The resulting suspension was cooled to 0° C. and 1.2 g (8.89 moles) of N,N-diethylcarbamoyl chloride was added by drop. The reaction mixture was heated to reflux overnight and the precipitated sodium chloride was removed by filtration. Concentration of the filtrate in vacuo gave 2.4 g (82percent) of 1(2 or 3)-N,N-diethylcarbamyl-<strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong> as a yellow oil. The structure was confirmed by n.m.r. and I.R.
1-(4-acetylphenyl)-4-diethylcarbamoylpiperazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium hydroxide; In chloroform;
Example 8 [1-(4-acetylphenyl)-4-diethylcarbamoylpiperazine and its hydrochloride] In 50 ml of chloroform was dissolved 10.2 g (0.05 mole) of 1-(4-acetylphenyl)-piperazine at room temperature, and 6.8 g (0.05 mole) of diethylcarbamoyl chloride was dropped to the solution over a period of 30 minutes. The mixture was stirred at room temperature for 5 hours, and the insoluble substance was removed. The filtrate was subjected to distillation under reduced pressure and the residue was made alkaline by 4 N aqueous solution of sodium hydroxide and extracted with 100 ml of toluene. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was recrystallized from a benzene-hexane mixed solvent to obtain 1-(4-acetylphenyl)-4-diethylcarbamoylpiperazine having a boiling point of 72 to 76 C.
Preparation of diethyl-carbamic acid 5-diethylcarbamoyloxy-2-isopropyl-4-[5-(4-methyl- piperazin-1 -ylmethyl)-1 ^-dihydro-isoindole^-carbonyli-cvclohexa-i ,3-dienyl esterTo a solution of (2,4-dihydroxy-5-isopropyl-phenyl)-[5-(4-methyl-piperazin-1-ylmethyl)-1 ,3- dihydro-isoindol-2-yl]-methanone (1.Og, 2.44 mmol) in THF (25 ml.) containing Et3N (0.68 ml_, 4.88 mmol) and N,N-4-dimethylaminopyridine (5 mg, 0.41 mmol) was added N,N- diethylcarbamoyl chloride (1.5 ml_, 1 1.62 mmol). The solution was heated to 60 0C for 18 h when EtOAc (50 mL) and 10% aq K2CO3 (50 mL) were added. The organic phase was washed with saturated brine (30 mL) and the organic phase was separated andevaporated to a small volume. A solution of the residue in DCM was applied to a column containing silica gel and the product eluted successively with DCM followed by 0.2% aqueous ammonia in 5%MeOH in DCM. The fractions containing product were evaporated from DCM followed by diethyl ether to give the title compound as a foam 1.07 g. 1 H NMR (400 MHz, DMSO-d6): 7.44 (1 H, d), 7.37-7.30 (1 H, m), 7.30-7.15 (2H, m), 7.01 (1 H, s), 4.75 (2H, s), 4.61 (2H, d), 3.56-3.40 (4H, m), 3.33 (4H, d), 3.24 (3H, d), 3.19-3.09 (2H, m), 3.09-2.95 (2H, m), 2.85-2.56 (4H, m), 2.42 (3H, s), 1.38-0.76 (18H, m); m/z 608 (MH).
With triethylamine; In tetrahydrofuran; at 100℃; for 6h;Microwave irradiation;
A mixture of <strong>[129722-25-4]dehydro-aripiprazole</strong> (1.50 g, 3.36 mmol), triethylamine (1.03 mL, 7.39 mmol), diethyl carbamoyl chloride (1.02 mL) were combined in tetrahydrofuran (30 mL). This was then heated to 100 C. for 6 hours by microwave. The reaction was quenched with water (50 mL) and extracted with dichloromethane (2×100 mL). The combined organics were dried (MgSO4) and concentrated. The crude product was purified by column chromatrography on silica eluting with ethyl acetate to 20% tetrahydrofuran/ethyl acetate to give the product. The product was then triturated with heptane to remove aliphatic impurities and then dried to give Compound 334 (1.54 g) as a light brown oil.1H-NMR (300 MHz, CDCl3) delta 8.10 (1H, d), 7.69 (1H, d), 7.31 (1H, d), 7.16-7.07 (4H, m), 6.99-6.92 (1H, m), 4.12 (2H, t), 3.54-3.39 (4H, 2×q), 3.12-2.96 (4H, br s), 2.78-2.54 (4H, br s), 2.50 (2H, t), 1.97-1.62 (4H, m), 1.32-1.16 (6H, 2×t). [M+H]+=545.2.
With sodium hydride; In 1,2-dimethoxyethane; mineral oil; at 23℃; for 84h;Inert atmosphere;
SI-6 (Table 4, entry 6). A round bottom flask was charged with NaH (0.33 g, 8.15 mmol, 1.2 equiv, 60percent dispersion in oil). A solution of <strong>[13523-92-7]N-methyl-5-hydroxyindole</strong> (SI- 5) (1.0 g, 6.79 mmol, 1 equiv) in DME (27 mL) was added dropwise via cannula to the NaH. A solution of diethylcarbamoyl chloride (0.875 mL, 6.45 mmol, 0.95 equiv) in DME (15 mL) was then added dropwise via cannula to the reaction vessel. The reaction was allowed to stir for 3.5 d, and then quenched with H20 (10 mL). The volatiles were removed under reduced pressure, and then Et20 (50 mL) and H20 (15 mL) were added. The layers were separated, and the organic layer was washed successively with 1 M KOH (20 mL) and H20 (20 mL). The combined aqueous layers were extracted with Et20 (3 x 20 mL). The combined organic layers were then washed with brine (20 mL), dried over MgS04, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (9: 1 Benzene:Et20) to yield N-methylindole-5 -carbamate SI-6 as a white solid (1.55g, 98percent> yield). R 0.44 (9: 1 Benzene :Et20); 1H NMR (500 MHz, CDC13): delta 7.33 (d, J= 2.5, 1H), 7.26 (d, J = 9.0, 1H), 7.05 (d, J = 3.0, 1H), 6.98 (dd, J = 8.5, 2.3, 1H), 6.43 (dd, J = 3.0, 0.5, 1H), 3.78 (s, 3H), 3.47 (bs, 2H), 3.41 (bs, 2H), 1.27 (bs, 3H), 1.21 (bs, 3H); 13C NMR (125 MHz, CDC13): delta 155.4, 145.1, 134.5, 129.8, 128.7, 116.3, 113.2, 109.4, 101.1, 42.3, 41.9, 33.1, 14.4, 13.6; IR (film): 2972, 1708, 1467, 1418, 1218, 1159 cm"1; HRMS- ESI (m/z) [M + Na]+ calcd for Ci4Hi8N202Na, 269.1266; found, 269.1267.
With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h;Reflux;
A representative procedure: Into a 25 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.18 g, 5 mol %) and 10 mL of 4-ethoxycarbonylphenylzinc bromide chloride (0.5 M in THF, 5.0 mmol). Next, diethylcarbamoyl chloride (0.54 g, 4.0 mmol) was added via a syringe. The resulting mixture was stirred at refluxing temperature for 24 h. Cooled down to room temperature and quenched with saturated NH4Cl solution, then extracted with ethyl acetate (10 mL × 3). Washed with saturated Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (20% ethyl acetate/80% heptane) afforded ethyl 4-(diethylcarbamoyl)benzoate (1c, 0.70 g) as a yellow oil in 70% isolated yield.
With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h;Reflux;
A representative procedure: Into a 25 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.18 g, 5 mol %) and 10 mL of 4-ethoxycarbonylphenylzinc bromide chloride (0.5 M in THF, 5.0 mmol). Next, diethylcarbamoyl chloride (0.54 g, 4.0 mmol) was added via a syringe. The resulting mixture was stirred at refluxing temperature for 24 h. Cooled down to room temperature and quenched with saturated NH4Cl solution, then extracted with ethyl acetate (10 mL × 3). Washed with saturated Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (20% ethyl acetate/80% heptane) afforded ethyl 4-(diethylcarbamoyl)benzoate (1c, 0.70 g) as a yellow oil in 70% isolated yield.
With triethylamine; In dichloromethane; at 20℃;Cooling with ice;
To a solution of 7- [4- (4-benzo [b] thiophen-4-yl-piperazin- 1-yl) -butoxy] -lH-quinolin-2-one (800 mg) synthesized in the same manner as in O2006/112464 (Example 1) in dichloromethane (20 ml) was added triethylamine (0.65 ml), with stirring under ice-cooling, diethylcarbamoylchloride (0.5 g) was added and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and the mixture wasextracted with ethyl acetate. The organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate : n-hexane=20 : 1) to give 7- [4- (4- benzo [b] thiophen-4-yl-piperazin-l-yl ) -butoxy] -quinolin-2-yl diethylcarbamate (120 mg) .oil: colorless1H-N R (CDC13) delta ppm : 1.23 (3H, t, J=7.1 Hz), 1.30 (3H, t, J=7.1 Hz), 1.72-1.84 (2H, m) , 1.86-1.98 (2H, m) , 2.54 (2H, t, J=7.5 Hz), 2.73 (4H, br) , 3.20 (4H, br) , 3.43 (2H, q, J=7.0 Hz), 3.52 (2H, q, J=7.1 Hz), 4.13 (2H, t, J=6.3 Hz), 6.89 (1H, d, J=7.2 Hz), 7.08 (1H, d, J=8.6 Hz), 7.16 (1H, dd, J=2.5, 8.9 Hz), 7.26 (1H, t, J=7.8 Hz), 7.34 (1H, d, J=2.4 Hz), 7.36-7.44 (2H, m) , 7.54 (1H, d, J=7.9 Hz), 7.68 (1H, d, J=8.9 Hz), 8.09 (1H, d, J=8.6 Hz)
120 mg
With triethylamine; In dichloromethane; at 20℃;Cooling with ice;
WO 2006/112464 (Example 1)Was synthesized in the same manner as7- [4- (4-benzo [b] thiophene-4-yl-piperazin-l-yl) -butoxy]-1 H-quinolin-2-one (800 mg)In dichloromethane (20 ml) was added triethylamine(0.65 ml), and the mixture was stirred under ice cooling,Diethylcarbamoyl chloride (0.5 g)Was added and the mixture was stirred at room temperature overnight.Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.The organic layer was dried over sodium sulfate,The solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography(Ethyl acetate: n-hexane = 20: 1)7- [4- (4-benzo [b] thiophene-4-yl-piperazin-l-yl)-Butoxy] -quinolin-2-yl diethylcarbamate(120 mg) was obtained.Oily matter: colorless
16 g ( 1 Mole) of phenyl acetic acid and 136 g (= 127 ml. 1 Mole) N.N-dicthylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask fitted with air condenser which is placed over a magnetic stirrer. To this, 98 g (96 ml, 1 .2 Mole) of 1-methylimidazole, which is an organic tertiary base is added using a pressure -equal izing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction mixture is stirred constantly for 30 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-diethyl-2-phenylacetamide (DEPA) is obtained by vacuum distillation of organic layer which is the product. Purity of the compound is analyzed using GC-MS which is more than 99.5%. And yield of hr product is 1 87 g (98%).
98%
With 1-methyl-1H-imidazole; at 20℃; for 0.5h;
Example 1 Preparation of N,N-Diethyl-2-phenyl acetamide (DEPA) [0093] 136 g (1 Mole) of phenyl acetic acid and 136 g (=127 ml, 1 Mole) N,N-diethyl carbamoyl chloride are taken in a 1 liter two-necked round-bottom flask fitted with air condenser which is placed over a magnetic stirrer. To this, 98 g (96 ml, 1.2 Mole) of I-methylimidazole, which is an organic tertiary base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction mixture is stirred constantly for 30 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-diethyl-2-phenylacetamide ( DEPA) is obtained by vacuum distillation of organic layer which is the product. [0094] Purity of the compound is analyzed using GC-MS which is more than 99.5%. And yield of hr product is 187 g (98%).
136 g ( 1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (= 1 27 ml. 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask lltted with air condenser which is placed over a magnetic stirrer. To this, 121 g ( 167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction m ixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-diethyl m-toluamide (DEET) is obtained by vacuum disti l lation of organic layer wh ich is the product. Purity of the compound is analyzed using GC-MS which is more than 99.5%. The yield of the product is 186 g (97.5%).
97.5%
With triethylamine; at 20℃; for 0.333333h;
Example 2 Preparation of N,N-Diethyl m-Toluamide (DEET) [0095] 136 g (1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (=127 ml, 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask fitted with air condenser which is placed over a magnetic stirrer. To this, 121 g (167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction mixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-Diethyl m-toluamide (DEET) is obtained by vacuum distillation of organic layer which is the product. [0096] Purity of the compound is analyzed using GC-MS which is more than 99.5%. The yield of the product is 186 g (97.5%).
N,N-diethyl-4.(pyridln-3-yl)-1 H-imldazole-1 -carboxamideCharge 3-(IH-imidazol-4-yl)pyridine (0.5 g, 3.44 mmcl) and Pyridine (2.5 ml). Charge diethylcarbamic chloride (0.467 g, 3.44 mmcl).The reaction mixture was heated to 90C and stir for lhr.Sample for TLC. Still starting material, more carbamoyl chloride (0.3g) was added. The mixture was stirred for lh and the reaction conversion was checked by TLC (DCM/MeOH, 9:1). No starting material left.The reaction was cooled to room temperature and the pyridine was removed.The mixture was diluted with sat NaHCO3 and DCM. The biphasic mixture was separated. The aqueous layer was washed with DCM.The combined organic layers were washed with sat NaHCO3, dried over Na2SO4, concentrated to dryness.Yellow oil (0. 835mg) was obtained in 94% molar yield; purity >95%1C NMR (150 MHz, CDCI3, 20C) 6: 150.8, 148,5, 146.7, 139.3, 137, 132.4, 129, 123.6, 113.8,42.8, 13.2
To the solution of 2-cyano-3-hydroxypyridine 16 (2 g, 16.6 mmol, 1 equiv) in 40 mL of pyridine at 0 C diethylcarbamoylchloride (2.2 mL, 2.37 g, 17.5mmol, 1.05 equiv) was added. The reaction mixture was stirred at the room temperature overnight. The solvent was removed in vacuum. The resulting crude material was treated with water. Then the mixture was neutralized with HCl, and the resulting product was extracted with ethyl ether, the extract was washed with aqueous 10% Na2CO3 and brine, dried over Na2SO4. The solvent was evaporated and product was dried in vacuum. The crude product was purified by column chromatography (silica gel, ethyl acetate/c-hexane = 1/2). Rf = 0.45 (ethyl acetate/c-hexane = 2/3). Yield 3.46 g, 95%. 1H NMR (400 MHz, CDCl3, delta): 1.21 (3H, t, J = 7.2 Hz, CH3); 1.30 (3H, t, J = 7.2 Hz, CH3); 3.38 (2H, q, J = 7.2 Hz, CH2); 3.49 (2H, q, J = 7.2 Hz, CH2); 7.49-7.52 (1H, dd, J = 8.5 Hz, J = 4.6 Hz, ArH); 7.82-7.84 (1H, dd, J = 8.5 Hz, J = 1.3 Hz, ArH); 8.47-8.49 (1H, dd, J = 4.6 Hz, J = 1.3 Hz, ArH). 13C NMR (100 MHz, CDCl3, delta): 13.34; 14.31; 42.61; 43.02; 114.69; 127.50; 131.23; 147.17; 151.56; 151.97. HRMS (ESI): m/z: calcd for C11H14N3O2 [M+H]+: 220.10860, found 220.10826.
95%
With pyridine; at 0 - 20℃;
2-Cyanopyridin-3-yl N,N-diethylcarbamate (17) To the solution of 2-cyano-3-hydroxypyridine 16 (2.00 g, 0.0 1665 mol, 1 equiv) in 40 mL of pyridine at 0 C diethylcarbamoylchloride (2.2 mL, 2.37 g, 0.01748 mol, 1.05 equiv) was added. The reaction mixture was stirred at the room temperature overnight. The solvent was removed in vacuum. The resulting crude material was treated withwater. Then the mixture was neutralized with HC1, and the resulting product was extracted with ethyl ether, the extract was washed with aqueous 10% Na2CO3 and brine, dried over Na2504. The solvent was evaporated and product was dried in vacuum. The crude product was purified by column chromatography (silica gel, ethyl acetate/chexane = 1/2). Rf = 0.45 (ethyl acetate/c-hexane = 2/3). Yield 3.46 g, 95%. ?H NMR(400 MHz, CDC13, oe): 1.21 (3H, t, J = 7.2 Hz, CH3); 1.30 (3H, t, J = 7.2 Hz, CH3); 3.38(2H, q, J = 7.2 Hz, CH2); 3.49 (2H, q, J = 7.2 Hz, CH2); 7.49-7.52 (1H, dd, J = 8.5 Hz, J= 4.6 Hz, ArH); 7.82-7.84 (1H, dd, J = 8.5 Hz, J = 1.3 Hz, ArH); 8.47-8.49 (1H, dd, J =4.6 Hz, J = 1.3 Hz, ArH). ?3C NMR (100 MHz, CDC13, oe): 13.34; 14.31; 42.61; 43.02;114.69; 127.50; 131.23; 147.17; 151.56; 151.97. HRMS (ESI): mlz: calcd forC11H14N302 [M+H]: 220.10860, found 220.10826.
95%
With pyridine; at 0℃; for 20h;
To the solution of 2-cyano-3-hydroxypyridine 16 (2.00 g, 0.01665 mol, 1 equiv) in 40 mL of pyridine at 0 C diethylcarbamoylchloride (2.2 mL, 2.37 g, 0.01748 mol, 1.05 equiv) was added. The reaction mixture was stirred at the room temperature overnight. The solvent was removed in vacuum. The resulting crude material was treated with water. Then the mixture was neutralized with HCl, and the resulting product was extracted with ethyl ether, the extract was washed with aqueous 10% Na2CO3 and brine, dried over Na2SO4. The solvent was evaporated and product was dried in vacuum. The crude product was purified by column chromatography (silica gel, ethyl acetate/c-hexane = 1/2). Rf = 0.45 (ethyl acetate/c-hexane = 2/3). Yield 3.46 g, 95%. 1H NMR (400 MHz, CDCl3, delta): 1.21 (3H, t, J = 7.2 Hz, CH3); 1.30 (3H, t, J = 7.2 Hz, CH3); 3.38 (2H, q, J = 7.2 Hz, CH2); 3.49 (2H, q, J = 7.2 Hz, CH2); 7.49-7.52 (1H, dd, J = 8.5 Hz, J = 4.6 Hz, ArH); 7.82-7.84 (1H, dd, J = 8.5 Hz, J = 1.3 Hz, ArH); 8.47-8.49 (1H, dd, J = 4.6 Hz, J = 1.3 Hz, ArH). 13C NMR (100 MHz, CDCl3, delta): 13.34; 14.31; 42.61; 43.02; 114.69; 127.50; 131.23; 147.17; 151.56; 151.97. HRMS (ESI): m/z: calcd for C11H14N3O2 [M+H]+: 220.10860, found 220.10826.
(S)-2-((R)-4-(diethylcarbamoyloxy)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate[ No CAS ]
(S)-2-((R)-3,4-bis(diethylcarbamoyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
20%; 37%
With pyridine; In toluene; at 20℃; for 48h;
Example 45 (Synthesis of (S)-2-((R)-4-(diethylcarbamoyloxy)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (Compound 1-244) and (S)-2-((R)-3,4-bis(diethylcarbamoyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (Compound 1-246)) First, 6-O-palmitoyl-L-ascorbic acid (2.00 g, 4.82 mmol) was dissolved in pyridine (15 mL), and the resulting solution was cooled in an ice bath containing added salt. A toluene solution (5 mL) containing diethylcarbamoyl chloride (0.70 g, 5.16 mmol) was then added dropwise. The temperature of the reaction solution was then gradually raised to room temperature, and the reaction was allowed to proceed at the same temperature for two days. Subsequently, the insoluble material was removed by filtration and washed with toluene. The filtrate was then concentrated, and the residue was purified by silica gel column chromatography, yielding (S)-2-((R)-4-(diethylcarbamoyloxy)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (compound 1-244) in an amount of 0.50 g, a yield of 37%, and (S)-2-((R)-3,4-bis(diethylcarbamoyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (compound 1-246) in an amount of 0.12 g, a yield of 20%.
Using a protocol adapted from a literature procedure,[4] a Schlenk flask was charged with NaH(0.0792 g, 1.98 mmol, 1.2 equiv, 60% dispersion in oil), and cooled to 0 C. Then a solution of <strong>[607-67-0]4-hydroxy-2-methylquinoline</strong> (0.263 g, 1.65 mmol, 1 equiv) in DMF (7.3 mL) was added dropwisevia syringe to the NaH. The resulting solution was warmed to r.t. for 10 min, and then cooled to 0C. A solution of diethyl carbamoyl chloride (0.250 mL, 1.98 mmol, 1.2 equiv) in DMF (2 mL)was then added dropwise via cannula to the reaction vessel. The reaction was warmed to r.t.,allowed to stir for 16 h, and then quenched with several drops of water. The reaction mixture waspoured into a separatory-funnel containing an aqueous solution of 5% LiCl (30 mL). 5 manualseparatory-funnel extractions were done in series using an aqueous solution of 5% LiCl as theaqueous phase and dichloromethane as the organic phase. The organic layers were combined andthe solvent was removed under reduced pressure. The solid material was dissolved in Et2O (50mL) and H2O (15 mL), and transferred to a separatory funnel. The layers were separated, and theorganic layer was washed with 1 M KOH (15 mL), then H2O (15 mL). The combined aqueouslayers were extracted with Et2O (3x20 mL). The combined organic layers were then washed withbrine (15 mL), dried over MgSO4, and concentrated under reduced pressure. The crude residuewas purified by flash chromatography 50% ethyl acetate/hexanes to yield carbamate SI-2 as awhite solid.
A solution of <strong>[116230-30-9]7-bromonaphthalen-2-ol</strong> (4.43 g, 20 mmol) in DME (30 mmol) was added dropwiseto a suspension of NaH (60% oil dispersion, 1.4 g, 30 mmol) in DME (15 mL) at 0 C, and themixture was stirred at room temperature for 10 min. Et2NCOCl (4.1 g, 30 mmol) and DMAP (24mg, 1 mol%) was then added to the reaction mixture and stirred at room temperature for 2 h. Thesolvent was removed in vacuo to give a residue, which was dissolved in EtOAc and filtered througha pad of silica gel. The filtrate was then concentrated in vacuo to give the crude product, which waspurified by flash column chromatography over silica gel (eluent: hexane/EtOAc = 10/1) to give 1k(6.3 g, 98%) as a colorless oil.Rf 0.39 (hexane/EtOAc = 5/1). Colorless oil (6.3 g, 98%).1H NMR (CDCl3, 400 MHz): delta 7.94 (d, J = 1.8 Hz, 1H), 7.79 (d, J = 9.2 Hz, 1H), 7.68 (d, J = 8.7Hz, 1H), 7.50 (dd, J = 8.9, 2.1 Hz, 2H), 7.30 (dd, J = 8.7, 2.3 Hz, 1H), 3.45 (m, 4H), 1.26 (m, 6H).13C NMR (CDCl3, 100 MHz): delta 154.1, 150.0, 135.0, 129.50, 129.47, 129.3, 129.1, 128.7, 122.2,120.5, 117.6, 42.3, 42.0, 14.3, 13.4.IR (ATR): 2974 w, 2930 w, 1716 s, 1629 w, 1504 w, 1473 w, 1415 m, 1381 w, 1358 w, 1272 m,1237 m, 1199 s, 1160 s, 1097 w, 1065 w, 973 w, 913 m, 838 w, 745 m.HRMS (EI): Calcd for C15H16BrNO2 321.0364, Found 321.0362.
With potassium carbonate; In acetonitrile; for 12h;Reflux;
Add 2.0 mmol to the reaction flask<strong>[480-41-1]Naringenin</strong> (1),7mmol of 10mmol anhydrous potassium carbonate and 50ml of acetonitrile, after stirring evenly,The reaction was stirred under reflux for 12 hours (the progress of the reaction was followed by TLC);After the completion of the reaction, the solvent was evaporated to dryness, evaporated, evaporated, evaporated, evaporated, evaporated, evaporated, The formic acid ester compound (I-2) is evaporated to dryness, and the residue is purified by column chromatography (dichloromethane:Acetone = 100:1 v/v), and the corresponding <strong>[480-41-1]naringenin</strong> carbamate compound (I-2) was obtained in a yield of 61.3%. The purity of the obtained target was more than 97% by HPLC.
(1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-octanamido-3-(pyrrolidin-1-yl)propyl diethylcarbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%
Eliglustat (0.300 g) was dissolved into THF (10.5 ml) at room temperature under nitrogen atmosphere. The reaction mass was cooled to 5-10 C under nitrogen atmosphere. NaH 55% (0.0388 g) was added to the reaction mass to get suspension and the reaction mass was stirred at 5-10 C for 15-20 min. Diethyl carbamic chloride (0.120 g) in THF (1 ml) was drop wise added to the reaction mass and the reaction mass was stirred at room temperature for 16-18 hrs light grey colored suspension formed after completion of addition completion of the reaction, the reaction mass was poured into water (20 ml) and product was extracted by dichloromethane (10 ml *2). The organic layer was separated, washed with saturated NaHCCh solution (5 ml *2). The organic layer was separated, dried over sodium sulphate and dried under vacuum at 40 C to afford the crude product. The crude product was purified by column chromatography using silica gel (100-200 mesh) with elution of 4-5% MeOH in dichloromethane to get pure product (0.320 g). Mass (m/z): 504.3 [M+H] Yield: 85%
With dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere;
General procedure: Acyl chloride (0.18 mmol, 1.1 eq) was added at 0 C to a solution of <strong>[436-77-1]fangchinoline</strong> (100 mg, 0.16 mmol) and DMAP (0.032 mmol, 0.2eq) in 2 mL dry CH2Cl2 under argon and stirred for 2-4 h. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted three times with CH2Cl2. The combined organic phase was dried over anhydrous magnesium sulfate before vacuum suction filtration. The removal of the solventin vacuo afforded the crude product, which was chromatographied on silica gel (CH2Cl2/MeOH, 50/1 v/v, 0.1% TEA) to provide the pureproduct 1a-1e, 2a-2g, 3a-3e and 4a-4h.
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