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Chemical Structure| 2387-23-7 Chemical Structure| 2387-23-7
Chemical Structure| 2387-23-7

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CAS No.: 2387-23-7

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1,3-Dicyclohexylurea(DCU) is an orally effective, soluble epoxy hydrolase (sEH) inhibitor. Oral 1,3-Dicyclohexylurea nanosuspension can enhance drug exposure in hypertensive rats and lower blood pressure.

Synonyms: N,N'-Dicyclohexylurea; NSC 17013; DCU

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Product Details of [ 2387-23-7 ]

CAS No. :2387-23-7
Formula : C13H24N2O
M.W : 224.34
SMILES Code : O=C(NC1CCCCC1)NC1CCCCC1
Synonyms :
N,N'-Dicyclohexylurea; NSC 17013; DCU
MDL No. :MFCD00003829
InChI Key :ADFXKUOMJKEIND-UHFFFAOYSA-N
Pubchem ID :4277

Safety of [ 2387-23-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis [ 2387-23-7 ]

* 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.

  • Downstream synthetic route of [ 2387-23-7 ]

[ 2387-23-7 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 2491-15-8 ]
  • [ 2387-23-7 ]
  • [ 101426-90-8 ]
  • 2
  • [ 485-89-2 ]
  • [ 2941-20-0 ]
  • [ 2387-23-7 ]
  • [ 174636-33-0 ]
YieldReaction ConditionsOperation in experiment
DESCRIPTION 1(S)-(-)-N-(a-ethylbenzyl)-3-hydroxy-2-phenyl-4-quinoline carboxamide 2.49 g (9.4 mmols) of <strong>[485-89-2]3-hydroxy-2-phenyl-4-quinoline carboxylic acid</strong> (CAS [485-89-2]) were suspended in 150 ml of a mixture of THF/MeCN 7:3, respectively; 1.40 g (10.3 mmols) of 1-hydroxybenzotriazole (HOBT) were added to the suspension and then 1.27 g (9.4 mmols) of (S)-(-)-1-phenylpropylamine, dissolved in 20 ml of methylene chloride were added dropwise over 10 minutes period. The reaction mixture was stirred at room temperature for 30 minutes and then 2.13 g (10.3 mmols) of dicyclohexylcarbodiimide (DCC), dissolved in 20 ml of methylene chloride, were added dropwise and the reaction stirred overnight. 20 ml of H2O were added and the reaction stirred 30 minutes, then the solvent was evaporated in vacuo to dryness. The residue was taken up in EtOAc, the precipitated dicyclohexylurea (DCU) was filtered off and the filtrate washed with water, 20% citric acid, 5% NaHCO3, brine and the organic layer dried over Na2SO4 and the solvent evaporated in vacuo. The residue was purified by silica-gel (60-240 mesh) flash column chromatography, eluting with a mixture of hexane/EtOAc 9:1, containing increasing amounts of EtOAc, until the ratio 7:3. The purified product was crystallized from i-PrOH to yield 1.75 g of the title compound as a white solid. C25H22N2O2 M.P.=168-168.4 C. M.W.=382.47 [a]D20=-28.5 (c=0.5, MeOH) Elemental analysis: Calcd. C, 78.51; H, 5.80; N, 7.33; Found C, 78.49; H, 5.84; N, 7.86. I.R. (Kbr): 3370; 1625; 1525 cm-1. 300 MHz 1H-NMR (DMSO-d6): d: 9.80 (s, 1H); 9.11 (d, 1H); 8.00-7.94 (m, 3H); 7.61-7.42 (m, 8H); 7.38 (dd, 2H);.7.28 (dd, 1H); 5.06 (dt, 1H); 1.82 (ddq, 2H); 0.97 (t, 3H). MS (EI; TSQ 700; source 200 C.; 70 eV; 200 A): 382 (M+.); 264; 247; 219.
  • 3
  • [ 98446-49-2 ]
  • [ 372-09-8 ]
  • [ 538-75-0 ]
  • [ 846023-24-3 ]
  • [ 2387-23-7 ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); at 10 - 20℃; for 2h;Product distribution / selectivity; [0059] A reaction flask was charged with dimethylformamide (DMF) (500 mL), 2,4-dichloro-5-methoxyaniline (100 g, 0.52 mol) and cyanoacetic acid (46.6 g, 0.55 mol). The mixture was cooled to 10 C. in an ice bath. To the cooled mixture was added, dropwise, a solution of N,N' dicyclohexylcarbodiimide (119.1 g, 0.58 mol) in DMF (240 mL) so as to keep the temperature below 15 C. After the addition was completed, cooling was discontinued and the reaction was stirred for 2 hours. The urea by-product was then removed via filtration and the cake was washed twice with DMF. To the filtrate was added 700 mL of water. The solid product emerged from solution. The slurry was cooled to 5 C. and held for at least 30 minutes. The product was collected by filtration and washed with water and then dried in vacuo at 60 C. to give 127.08 g of light tan solid.
  • 4
  • [ 15761-38-3 ]
  • [ 1479-58-9 ]
  • (S)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
  • [ 2387-23-7 ]
YieldReaction ConditionsOperation in experiment
79% With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h; {1-[4-Bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 116.; To a stirred solution of <strong>[1479-58-9](2-amino-5-bromophenyl)-(2-fluoro-phenyl)-methanone</strong> (60 g, 204 mmol) 115 and the N-Boc-L-alanine 107 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid residue 116 was purified by recrystallization from hexane and EtOAc to afford 116 (74.9 g, 79percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=-59.1 (c 0.51, EtOAc).
  • 5
  • [ 3744-87-4 ]
  • [ 1479-58-9 ]
  • (R)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
  • [ 2387-23-7 ]
YieldReaction ConditionsOperation in experiment
77% With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h; {1-[4-Bromo-2-(2-fluorobenzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 136; To a stirred solution of (2-amino-5-bromophenyl)-(2'-fluoro-phenyl)-methanone 115 (60 g, 204 mmol) and the N-Boc-D-alanine 129 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid product 136 was purified by recrystallization from hexane and EtoAc to afford 136 (73 g, 77percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=59.6 (c 0.51, EtOAc).
  • 6
  • [ 54060-30-9 ]
  • [ 119389-05-8 ]
  • N-(3-ethynylphenyl)-4'-phenylethynylphthalisoimide [ No CAS ]
  • [ 2387-23-7 ]
  • 7
  • [ 623-57-4 ]
  • [ 1510-21-0 ]
  • [ 926890-44-0 ]
  • [ 2387-23-7 ]
YieldReaction ConditionsOperation in experiment
34% With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 6.25h;Product distribution / selectivity; To a solution of 3-dimethylamino-l,2-propanediol (0.5g, 3,6 mmoles) in 10 mL dichloromethane was added cholesterylhemisuccinic acid (1.75g, 3.6 mmoles) and DCC (1.48g, 7.2 mmoles) at 0°C. The reaction was allowed to proceed from 0°C (15 mins) to room temperature for 6 hours. DCU was filtered off and the filtrate was evaporated on a rotary evaporator and loaded on a silica gel (230-400 mesh). The desired product was EPO <DP n="57"/>eluted with 4-5percent methanol in chloroform (v/v) to give a colorless thick liquid (0.834g, Rf -0.5 in 10percent methanol in chloroform, yield 34percent).1HNMR (400 MHz, CDCl3): delta 5.36 (d, J= 4.0 Hz, IH), 4.67-4.56 (m, IH), 4.19 (dd, J= 11.6, 3.6 Hz, IH), 4.04 (dd, J= 11.6, 6.0 Hz, IH), 3.97-3.89 (m, IH), 2.70-2.56 (m, 4H), 2.44 (t, J= 10.0 Hz, IH), 2.36-2.23 (m, 9H), 2.05-1.75 (m, 5H), 1.66-0.80 (m, 33H), 0.67 (s, 3H).
34% With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 6.08333h;Product distribution / selectivity; An alternative synthesis procedure is as follows: to an ice-cooled solution of cholesteryl hemisuccinate (4.09 g, 8.42 mmol) in DMF (35 mL) 3-(dimethylamino)-l,2- propandiol (1.0 mL, 8.42 mmol) was added N,N'-dicyclohexylcarbodiimide (3.47 g, 16.84 mmol). After 5 min., the ice bath was removed and the solution was stirred for an additional 6 h at room temperature. The resulting precipitation of dicyclohexylurea was removed by filtration. The filtrate was transferred to a 100 mL round bottom flask and concentrated to dryness under vacuum. The pasty mass was dissolved in CHCl3 (200 mL) and washed with H2O (30 mL), saturated aqueous NaCl (30 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 5percent MeOH in CHCl3) furnished IV (1.68 g, 34percent) as wax. NMR spectra coordinates are as follows: 1H NMR (CDCl3): delta 5.36 (d, J= 4.0 Hz, IH), 4.67-4.56 (m, IH), 4.19 (dd, J = 11.6, 3.6 Hz, IH), 4.04 (dd, J= 11.6, 6.0 Hz, IH), 3.97-3.89 (m, IH), 2.70-2.56 (m, 4H), 2.44 (t, J= 10.0 Hz, IH), 2.36-2.23 (m, 9H), 2.05-1.75 (m, 5H), 1.66-0.80 (m, 33H), 0.67 (s, 3H).
  • 8
  • [ 1823-59-2 ]
  • [ 10526-07-5 ]
  • [ 119389-05-8 ]
  • poly(4,4'-oxydiphthalic acid dianhydride-co-1,3-bis(3-aminophenoxy)benzene-co-4-phenylethynylphthalic anhydride) [ No CAS ]
  • [ 2387-23-7 ]
 

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