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[ CAS No. 3218-02-8 ] {[proInfo.proName]}

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Product Details of [ 3218-02-8 ]

CAS No. :3218-02-8 MDL No. :MFCD00001520
Formula : C7H15N Boiling Point : -
Linear Structure Formula :- InChI Key :AVKNGPAMCBSNSO-UHFFFAOYSA-N
M.W : 113.20 Pubchem ID :76688
Synonyms :

Safety of [ 3218-02-8 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2734
Hazard Statements:H225-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3218-02-8 ]

* 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 [ 3218-02-8 ]

[ 3218-02-8 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 14527-26-5 ]
  • [ 3218-02-8 ]
  • [ 45957-30-0 ]
  • 4
  • [ 5241-64-5 ]
  • [ 3218-02-8 ]
  • [1-(Cyclohexylmethyl-carbamoyl)-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 5
  • [ 924-44-7 ]
  • [ 931-53-3 ]
  • [ 141871-02-5 ]
  • [ 3218-02-8 ]
  • 2-[2-(<i>tert</i>-butoxycarbonyl-methyl-amino)-benzoyl]-cyclohexylmethyl-amino}-<i>N</i>-cyclohexyl-malonamic acid ethyl ester [ No CAS ]
  • 6
  • [ 7782-77-6 ]
  • [ 3218-02-8 ]
  • [ 590-67-0 ]
  • [ 502-41-0 ]
  • [ 100-49-2 ]
  • 7
  • [ 2004-07-1 ]
  • [ 3218-02-8 ]
  • 2-amino-N6-(cyclohexylmethyl)adenosine [ No CAS ]
  • 8
  • [ 69812-29-9 ]
  • [ 16590-41-3 ]
  • [ 3218-02-8 ]
  • C33H44N4O6S2 [ No CAS ]
  • 9
  • [ 104-03-0 ]
  • [ 136030-33-6 ]
  • [ 18637-83-7 ]
  • [ 3218-02-8 ]
  • <i>N</i>-cyclohexylmethyl-2-[4-(1,3,4-trioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-<i>b</i>]isoquinolin-2-yl)-phenyl]-acetamide [ No CAS ]
  • 10
  • [ 3218-02-8 ]
  • [ 216699-86-4 ]
  • cyclohexylmethyl-(6,7-dimethoxy-quinoxalin-2-yl)-amine [ No CAS ]
  • 11
  • [ 132684-59-4 ]
  • [ 3218-02-8 ]
  • [ 345347-68-4 ]
  • 5-(4-formyl-3,5-dimethoxyphenoxy)valeric aldehyde linker on a polyethylene glycol resin [ No CAS ]
  • 2-butyl-<i>N</i>1-[1-(cyclohexylmethyl-carbamoyl)-3-phenyl-propyl]-<i>N</i>4-hydroxy-succinamide [ No CAS ]
  • 12
  • [ 3218-02-8 ]
  • [ 153463-65-1 ]
  • 3-cyclohexylmethylamino-5-chloro-4-pyridinecarbonitrile [ No CAS ]
  • 13
  • [ 841276-88-8 ]
  • [ 6342-77-4 ]
  • [ 3218-02-8 ]
  • <i>N</i>-(1-cyclohexylmethyl-6-nitro-2-oxo-1,2,3,4-tetrahydro-quinolin-4-yl)-3-(2-methoxy-phenyl)-propionamide [ No CAS ]
  • 14
  • [ 35998-96-0 ]
  • [ 98-88-4 ]
  • [ 75318-43-3 ]
  • [ 3218-02-8 ]
  • 6-benzamido-2-cyano-3-cyclohexanemethylquinazolin-4(3H)-one [ No CAS ]
  • 15
  • [ 27329-27-7 ]
  • [ 75318-43-3 ]
  • [ 3218-02-8 ]
  • 2-cyano-3-cyclohexanemethyl-7-methylquinazolin-4(3H)-one [ No CAS ]
  • 16
  • [ 1070-70-8 ]
  • [ 3218-02-8 ]
  • polymer, Mw = 16380, PDI = 2.60; monomer(s): 1,4-butanediol diacrylate; 2-cyclohexyl-methylamine [ No CAS ]
  • 17
  • [ 56107-02-9 ]
  • [ 3218-02-8 ]
  • [ 917953-84-5 ]
  • 18
  • [ 3218-02-8 ]
  • [ 61940-21-4 ]
  • [ 959737-79-2 ]
YieldReaction ConditionsOperation in experiment
75% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃; for 3h; Step B: 2-(Cyclohexylmethyl)-7-nitroisoindolialpha-l-one; Cyclohexylmethylamine (1.63 mL, 12.5 mmol), followed by DIPEA (4.4 mL, 25 mmol) were added to a stirred solution of methyl-2-bromomethyl-6-nitro-benzoate (3.43 g, 12.5 mmol) in DMF (50 mL). The mixture was stirred at 80 0C for 3 h, concentrated in vacuo, diluted with CH2Cl2 (150 mL), washed with saturated NaHCC>3 solution (2x50 mL), brine (50 mL), dried over Na2SO4, filtered and evaporated. Flash chromatography of the residue over silica gel, using EtOAc/hexanes (1:5 to 1:2) gave the title compound, 2.6 g (75%) as a brown solid. 1H NMR (400 MHz, CHLOROFORM-D) delta 0.94 - 1.12 (m, 2 H), 1.13 - 1.30 (m, 3 H), 1.62 - 1.82 (m, 6 H), 3.44 (d, 2 H), 4.42 (s, 2 H), 7.60 - 7.71 (m, 3 H).
  • 19
  • [ 2605-14-3 ]
  • [ 3218-02-8 ]
  • [ 953771-32-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 105 - 110℃; for 66h; Step 1. Preparation of N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine To the solution of <strong>[2605-14-3]2-chloro-6-methoxybenzo[d]thiazole</strong> (900 mg, 4.5 mmol) in 4.5 ml of NMP was added cyclohexylmethanamine (865 mg, 7.65 mmol) and DIPEA (1.57 ml, 9.0 mmol). The reaction solution was stirred at 105-110 C. for 66 hours. The reaction was worked up by adding 250 ml ethyl acetate and washed with 2*60 ml of saturated NaHCO3, 3*60 ml water, 1*60 ml saturated NaCl, dried with sodium sulfate, filtered and concentrated in vacuo to give N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine as solid (1.18 grams). ES/MS m/z 277.1 (MH+).
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 105 - 110℃; for 66h; To a solution of <strong>[2605-14-3]2-chloro-6-methoxybenzo[d]thiazole</strong> (900 mg, 4.5 mmol) in 4.5 mL of NMP was added cyclohexylmethanamine (865 mg, 7.65 mmol) and DIPEA (1.57 mL, 9.0 mmol). The reaction solution was stirred at 105-110 C for 66 hours. The reaction was diluted with EtOAc (250 mL) and washed with saturated NaHCO3 (2x 60 mL), water (3x 60 mL), saturated NaCl (60 mL), dried with sodium sulfate, filtered and concentrated in vacuo to give N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine as a solid (1.18 grams). ES/MS m/z 277.1 (MH+).
  • 20
  • [ 723280-98-6 ]
  • [ 3218-02-8 ]
  • [ 723283-76-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; for 18h; Under a nitrogen atmosphere, cyclohexylmethylamine (40.9 ML, 315 mmol) was added dropwise to a solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (30.0 g, 105 mmol) in dichloromethane (524 mL). The reaction was stirred for 18 hours at ambient temperature and then concentrated under reduced pressure. Water (200 mL) was added to the residue, and the mixture was stirred for three hours. Acetonitrile was added; a precipitate formed. The solid was isolated by filtration, dried under a flow of air for two hours, and recrystallized from acetonitrile to provide 24.0 g of (7-bromo-3-nitroquinolin-4- yl) cyclohexylmethylamine as a yellow solid.
  • 21
  • [ 189321-66-2 ]
  • [ 3218-02-8 ]
  • [ 878010-29-8 ]
YieldReaction ConditionsOperation in experiment
To a 20 mL tube was placed PS-DCC (832 mg, 0. 018 mmol, 1.38 [MMOL/G),] HOBt (109 mg, 0.81 [MMOL),] and a 5: 1: 1 mixture of CHC13 : CH3CN: tBuOH. Then, cyclohexylmethyl amine [(65] [UL,] 0.5 mmol) and (R, S)-Boc-2- carboxymorpholine (125 mg, 0.54 mmol) were added, and the vial was placed on a GlasCol orbital rotator for 16 hours. After this time, [MP-CARBONATE] (480 mg, 1.62 mmol, 3.38 mmol/g) was added to scavenge the HOBt and excess (R, S)-Boc-2- carboxymorpholine. Three hours later, the vial's contents were filtered through an Applied Separations filter tube, washed with DCM (3 x 3 mL) and concentrated in an HTII-12 Genevac unit to afford an yellow oil. This material was then dissolved in DCM (2 [ML)] and 4 N HCl/dioxane (2 [ML)] added. After 10 minutes, the solvent was evapoarted under a stream of nitrogen gas and purified/free-based by standard SCX SPE. Concentration provided a colorless oil, N- (cyclohexylmethyl) morpholine-2-carboxamide, 102 mg (90%) -a single peak (214 nm and ELSD) at 2.06 min [(CH3CN/H20/1%] TFA, 4 min gradient). To an 8 mL vial was placed ethyl [5-BROMO-3-(CHLOROSULFONYL)-1-(PHENYLSULFONYL)-LH-INDOLE-2-] carboxylate (50 mg, 0.099 mmol), PS-NMM (58 mg, 0.216 mmol, 3.72 mmol/g), PS- DMAP (37 mg, 0.05 mmol, 1.48 mmol/g) and DCM. Then, N- (cyclohexylmethyl) [MORPHOLINE-2-CARBOXAMIDE] [(18] mg, 0. 08 mmol) was added, and the vial placed on a GlasCol orbital rotator for 16 hours. After this time, PS- triamine resin (75 mg, 0. [108] mmol, 1.44 mmol/g) was added to the vial to scavenge excess sulfonyl chloride. Three hours later, the vial's contents were filtered through an Applied Separations filter tube, washed with DCM (3 x 3 mL) and concentrated in an HTII-12 Genevac unit to afford an yellow solid. This material was then dissolved in 2 M NH3/EtOH, sealed in a scintillation vial and heated to 90 degrees on a J-KEM heater/shaker block for 3 hours. The vial was then dried in an HTII-12 Genevac unit to afford a brown solid. This material was then purified by Mass Guided HPLC on an Agilent 1100 Purification unit to afford a white crystalline solid. Analytical LCMS: single peak (214 nm and ELSD) at 3.35 min [(CH3CN/H20/1%] TFA, 4 min gradient). IH NMR (300 MHz, DMSO-d6) : [8] 8.2 (s, 2H), 7.99 (s, 1H), 7.39 [(M,] 2H), 7.48 [(M,] 2H), 3.95 [(T,] J=11 Hz, 2H), 3.63 [(M,] 2H), 3.44 (d, [J=11.] 4 Hz, [1H),] 2.48 [(M,] 2H), 2.3 (t, [J=18] Hz, 1H), 1.56 [(M,] 6H), 1.34 [(M,] 2H), 1.08 [(M,] 2H), 0.77 [(M,] [2H)] ppm. HRMS calc'd for [C21H27BRN405S,] 527. [0958] ; found, 527.0940.
  • 22
  • [ 351-32-6 ]
  • [ 3218-02-8 ]
  • [ 809237-74-9 ]
YieldReaction ConditionsOperation in experiment
100% With sodium carbonate; In ethanol; at 60℃; for 48h;Heating; Cyclohexylmethylamine (2.86 mL, 2.49 g, 22.0 mmol ) was added to a mixture of <strong>[351-32-6]N-(4-fluoro-3-nitrophenyl)acetamide</strong> (3.96 g, 20.0 mmol) and sodium carbonate (4.66 g, 44 mmol) in EtOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60 C, and diluted with H2O (800 mL). The orange solid was precipitated out and collected to give the desired title product (6.60 g, 100%). MS (ESI) (M+H)+: 292.32.
100% With sodium carbonate; In ethanol; at 20 - 60℃; for 48h; Step C. N-{4-[(CYCLOHEXYLMETHYL) AMINO]-3-NITROPHENYL} ACETAMIDE; Cyclohexylmethylamine (2.86 mL, 2.49 g, 22.0 mmol) was added to a mixture OF N- (4-fluoro-3-nitrophenyl) acetamide (3.96 g, 20.0 mmol) and sodium carbonate (4.66 g, 44 mmol) in ETOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60 C, and diluted with H20 (800 mL). The orange solid was precipitated out and collected to give the desired product (6.60 g, 100%). MS (ESI) (M+H) + : 292.32.
100% With sodium carbonate; In ethanol; at 20 - 60℃; for 48h; Cyclohexylmethylamine (2.86 mL, 2.49 g, 22.0 mmol) was added to a mixture of <strong>[351-32-6]N-(4-fluoro-3-nitrophenyl)acetamide</strong> (3.96 g, 20.0 mmol) and sodium carbonate (4.66 g, 44 mmol) in EtOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60 C., and diluted with H2O (800 mL). The orange solid was precipitated out and collected to give the desired product (6.60 g, 100%). MS (ESI) (M+H)+: 292.32.
100% With sodium carbonate; In ethanol; at 20 - 60℃; for 48h;Product distribution / selectivity; Step B. N-{4-[(CYCLOHEXYLMETHYL) AMINO]-3-NITROPHENYL} ACETAMIDE; CYCLOHEXYLMETHYLAMINE (2. 86 mL, 2.49 g, 22.0 mmol) was added to a mixture OF N- (4-fluoro-3-nitrophenyl) acetamide (3.96 g, 20.0 mmol) (for preparation, see Example 33, Step B) and sodium carbonate (4.66 g, 44 mmol) in EtOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60 C, and diluted with H20 (800 mL). The orange solid was precipitated out and collected to give the title product (6.60 g, 100%). MS (ESI) (M+H) + : 292.3.
100% With sodium carbonate; In ethanol; at 20 - 60℃; for 48h;Product distribution / selectivity; Step C. N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl} acetamide; Cyclohexylmethylamine (2.86 mL, 2.49 g, 22.0 mmol) was added to a mixture OF AT- (4-fluoro-3-nitrophenyl) acetamide (3.96 g, 20.0 mmol) and sodium carbonate (4.66 g, 44 mmol) in EtOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60 C, and diluted with H20 (800 mL). The orange solid was precipitated out and collected to give the title product (6. 60 g, 100%). MS (ESI) (M+H) + : 292.3.
99% With triethylamine; In ethanol; at 75℃;Product distribution / selectivity; Step B. N-{4-[(CYCLOHESYLMETHYL) AMINO]-3-NITROPHENYL} ACETAMIDE; N-(4-Fluoro-3-nitrophenyl) acetamide (500 mg, 2.52 mmol) and cyclohexanemethylamine (0.400 mL, 3.02 mmol) were stirred in 15 mL OF ETOH containing TEA (0.525 mL, 3. 78 mmol) at 75C overnight. The solvent was concentrated. The residue was dissolved in EtOAc and washed with aqueous 5% KHS04, saturated aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The solvent was evaporated. Yield : 735 mg (99%) ;'H NMR (400 MHz, CHLOROFORM-D): 8 1.03 (m, 2 H), 1.25 (m, 3 H), 1.62 (m, 1 H), 1.69 (m, 1 H), 1.76 (m, 1 H), 1.79 (m, 1 H), 1.82 (m, 1 H), 1.86 (m, 1 H), 2.17 (s, 3 H), 3.14 (dd, J=6. 25, 4.30 Hz, 2 H), 6.83 (d, J=9.37 Hz, 1 H), 7.20 (m, 1 H), 7.78 (dd, J=9.28, 2.64 Hz, 1 H), 8.07 (d, J=2.54 Hz, 1 H), 8.12 (m, 1 H).
99% With triethylamine; In ethanol; at 75℃;Product distribution / selectivity; Step B. N-{4-[(Cyclohexylmethyl)amino]-3-nitrophenyl}acetamide; N- (4-FLUORO-3-NITROPHENYL) acetamide (500 mg, 2. 52 mmol) and CYCLOHEXANEMETHYLAMINE (0.400 mL, 3.02 mmol) were stirred in 15 mL OF ETOH containing TEA (0.525 mL, 3. 78 mmol) at 75C overnight. The solvent was concentrated. The residue was dissolved in EtOAc and washed with aqueous 5% KHS04, saturated aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The solvent was evaporated. Yield: 735 mg (99%) ; LH NMR (400 MHz, CHLOROFORM-D): 8 1.03 (m, 2 H), 1.25 (M, 3 H), 1.62 (M, 1 H), 1.69 (m, 1 H), 1.76 (m, 1 H), 1.79 (m, 1 H), 1. 82 (m, 1 H), 1.86 (m, 1 H), 2. 17 (s, 3 H), 3.14 (dd, J=6.25, 4.30 Hz, 2 H), 6.83 (d, J=9.37 Hz, 1 H), 7.20 (m, 1 H), 7. 78 (dd, J=9.28, 2.64 Hz, 1 H), 8. 07 (d, J=2.54 Hz, 1 H), 8.12 (m, 1 H).

  • 23
  • [ 22280-56-4 ]
  • [ 3218-02-8 ]
  • [ 773147-98-1 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine; In ethanol; for 12h;Heating / reflux; To a solution of <strong>[22280-56-4]2-chloro-3-methyl-5-nitropyridine</strong> (3.45 g, 20 mmol) in ETOH (100 mL) and triethylamine (5 ML) was added cyclohexylmethylamine (4.52 g, 40 mmol) at room temperature. The reaction mixture was refluxed for 12 hr, allowed to cool down to room temperature. After condensation, the residue was diluted with AcOEt, washed with 1 N NH40H and brine, dried over MGS04. Removal of solvents provided the desired product (4.90 g, 98 %), which was used directly in the next STEP. H-NMR (CDCI3) : 8 1.02 (m, 2H), 1.23 (m, 3H), 1.75 (m, 6H), 2.16 (s, 3H), 3.46 (m, 2H), 4.98 (brs, 1H), 8. 00 (s, 1H), 8. 96 (s, 1H). MS (ESI) (M+H) + 250.31
  • 24
  • 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride [ No CAS ]
  • [ 80029-43-2 ]
  • [ 3218-02-8 ]
  • [ 197507-59-8 ]
  • [1,6]naphthyridine-2-carboxylic acid cyclohexyl-methylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In N,N-dimethyl-formamide; Compound #19 <strong>[197507-59-8][1,6]naphthyridine-2-carboxylic acid</strong> cyclohexyl-methylamide To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (1.0 mL) at room temperature was added sequentially 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), cyclohexanemethylamine (57.2 muL, 0.431 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum. Flash column chromatography of the residue (100% ethyl acetate) afforded the desired product as a white solid (74.9 mg, 97%): m.p. 62-63 C.
  • 25
  • [ 3017-32-1 ]
  • [ 525-03-1 ]
  • [ 3218-02-8 ]
  • [ 294181-72-9 ]
  • [ 762241-25-8 ]
YieldReaction ConditionsOperation in experiment
It is disclosed herein that the display of side chains identified as activein galanin or those of the nonpeptide galanin receptor agonist galnon on arigid platform creates a compound capable of recognition by the receptorGalR1. Mixtures of 3 to 4 amines were coupled to the triacid platform (D. Mink,et al., Tetrahedron Lett, (1998) 39, 5709-5712; G. Haberhauer, et al.,Tetrahedron Lett, (2000) 41, 5013-5016; and L. Somogyi, et al., Tetrahedron,(2001) 57, 1699-1708) and obtained small combinatorial libraries. Activemixtures were obtained (after deblocking with trifluoroacetic acid) from theamines shown: cyclohexylmethyl amine, 2; fluorenyl amine 3 ande-t-BOC-/-lysine methyl ester 4. This mixture (11 compounds) was fractionatedby HPLC and the most active compound (structure 5, Galmic, or itscyclodiastereomer) was identified by mass spectrometry. The individualmolecule was prepared by total synthesis which will be described elsewhere. Physical Characterization of Galmic:1H NMR-300 MHz (CDCIs): 9.01 (s, NH); 8.94 (s, NH); 8.89 (s, NH); 7.97 (sbroad, 3H); 7.65 (d, J=7.5 Hz, 2H); 7.55 (d, J=7.2 Hz, 1H); 7.42-7.19 (m, 5H);6.87 (pseudo t, J=5.4 Hz, 1H); 6.15 (d, J=8.4 Hz, 1H); 4.55 (m broad, 1H); 3.61(s, 3H); 3.38 (s broad, 1H); 3.12 (m, 1H); 2.90 (m, 3H); 2.70 (s, 3H); 2.65 (s,6H); 2.19 (s, 3H); 2.09 (s, 3H); 2.04 (s, 3H); 2.00-1.28 (m, 14H); 1.20-1.04 (m,3H); 0.92-0.76 (m, 2H).13C NMR-75 (CDCIs): 171.61; 168.81; 167.39; 160.44;160.41; 160.11; 159.97; 159.17; 156.09; 156.03; 155.91; 143.62; 143.39;140.50; 140.43; 128.67 (CH); 128.58 (CH); 127.85 (CH); 127.65 (CH); 124.97(CH); 124.72 (CH); 119.87 (CH); 60.68; 60.45; 59.90; 55.34 (CH); 52.46 (CHs);52.16 (CH); 46.27 (CHa); 39.55 (CHa); 37.74 (CH); 30.63 (CHa); 26.43 (CHa);26.23 (CHa); 25.80 (CHa); 21.69 (CHs); 21.50 (CHs); 21.44 (CHs); 11.89 (3CHs). MALDI-FTMS [M+H]+: expected: 989.4510; observed: 989.4508.
  • 26
  • [ 10130-87-7 ]
  • [ 3218-02-8 ]
  • [ 874569-02-5 ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine; In dichloromethane; (cyclohexyl methyl)[(2- methoxyphenyl)sulfonyl]amine was prepared by treating cyclohexylmethyl amine (0.23 g, 2mmols) with 2-methoxybenzenesulfonylchloride (0.41 g, 2 mmols) in dichloromethane (10 ml) in presence of diisopropylethylamine (0.7 ml 4 mmols). Yield: 0.53 g (94%). MH+: 284
  • 27
  • [ 43207-78-9 ]
  • [ 508240-54-8 ]
  • [ 3218-02-8 ]
  • [ 508239-44-9 ]
YieldReaction ConditionsOperation in experiment
31% EXAMPLE 427 5-Cyclohexylmethylamino-2-(2-furyl)-8-(7-methoxy-1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidine (Compound 428) The subject compound (31%) was obtained as a pale brown oily matter from 8-formyl-2-(2-furyl)-5-methylthio[1,2,4]triazolo[1,5-c]pyrimidine, cyclohexanemethylamine and <strong>[43207-78-9]7-methoxy-<strong>[43207-78-9]1,2,3,4-tetrahydroisoquinoline</strong></strong> in a manner similar to that in Example 315. APCIMS m/z: [M+H]+ 473
  • 28
  • [ 3218-02-8 ]
  • [ 102-83-0 ]
  • [ 245421-04-9 ]
  • [ 1018478-87-9 ]
  • 29
  • [ 108-77-0 ]
  • [ 366-99-4 ]
  • [ 22795-99-9 ]
  • [ 3218-02-8 ]
  • [ 502767-57-9 ]
YieldReaction ConditionsOperation in experiment
43.7% Example 43 Synthesis of N2-cyclohexylmethyl-N4-((S)-1-ethyl-pyrrolidin-2-ylmethyl)-N6-(3-fluoro-4-methoxphenyl)-1,3,5-triazine-2,4,6-triamine (141) To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20° C. was added 3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of N,N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at RT. Then, S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced. The crude material was purified by column chromatography eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp 68-69° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 8.2 min, 97.1percent purity; MS (ESI): m/z 458 (M+H, 100), 362 (2.8), 230 (85.4).
43.7% To a mixture of cyanuric chloride (0.368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) inCH3CN followed by the additionof N, N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at RT. Then, S-(-)- 2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced. The crude material was purified by column chromatography eluting with 96: 3: 1 methylene chloride: methanol: cone. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp68-69 OC ; HPLC: Inertsil ODS-3V C18, 40: 30: 30[KH2P04(0. 01 M, pH3. 2) :CH30H : CH3CN], 264nm, Rt 8.2 min, 97.1percent purity ; MS (ESI):lnlz 458 (M+H, 100), 362 (2.8), 230(85. 4).
  • 30
  • [ 213598-05-1 ]
  • [ 3218-02-8 ]
  • [ 1042391-74-1 ]
  • 31
  • [ 100-49-2 ]
  • [ 3218-02-8 ]
  • N-cyclohexylmethylidene-1-cyclohexylmethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonia;carbonylchlorohydrido(4,5-bis((diisopropylphosphino)methyl)acridine)ruthenium(II); In toluene; under 5700.38 Torr; for 25h;Reflux;Product distribution / selectivity; Complex 1 (0.01 mmol), alcohol (10 mmol ), and a solvent (3 mL, if applicable) were added to a 90 mL Fischer-Porter tube under an atmosphere of purified nitrogen in a Vacuum Atmospheres glovebox. The tube was taken out of the box and ammonia (7.5 atm) was charged into the Fischer-Porter tube and the reaction mixture was refluxed in an oil bath covered by a protective shield for the specified time (Tables 1-3 in the reports). After cooling to room temperature, the products were analyzed by GC with toluene or mesitylene as an internal standard, using a HP-5 cross linked 5% PH ME Siloxane column (30m x 0.32mm x 0.25 mum film thickness) on a HP 6890 series GC system.
  • 32
  • [ 3218-02-8 ]
  • [ 766-05-2 ]
  • [ 1122-56-1 ]
  • [ 98-89-5 ]
  • 33
  • [ 67899-00-7 ]
  • [ 3218-02-8 ]
  • [ 1152209-90-9 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 100℃; for 2h; To 4 mL of DMF were added 0.50 g of 2-amino-4- methylthiazole-5-carboxylic acid, 0.56 g of 1- hydroxybenzotriazole, 0.80 g of WSC and 0.47 g of cyclohexylmethylamine, and the mixture was stirred at 1000C for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, added to an aqueous saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.58 g of N-cyclohexylmethyl-2- amino-4-methylthiazole-5-carboxamide (hereinafter referred to as "the present compound (2)") . The present compound (2) <n="37"/>1H-NMR (CDCl3) delta: 0.91-1.30 (5H, m) , 1.49-1.76 (6H, m) , 2.49 (3H, s), 3.22 (2H, t, J = 6.4 Hz), 5.28 (2H, br s), 5.54 (IH, br s) .
  • 34
  • [ 50916-55-7 ]
  • [ 3282-30-2 ]
  • [ 3218-02-8 ]
  • [ 1010833-26-7 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 3-(2-bromoacetyl)benzonitrile; cyclohexylmethylamine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20℃; Cooling with ice; Inert atmosphere; Stage #2: pivaloyl chloride In tetrahydrofuran for 1h; Stage #3: With 2,2,2-trifluoroacetic acid ammonia at 140℃; for 0.25h; Inert atmosphere; 1 EXAMPLE 1 3-(2-tert-Butyl-1-cyclohexylmethyl-1H-imidazol-4-yl)benzonitrile (Compound 1) ; Under a nitrogen atmosphere, cyclohexanemethylamine (1.04 mL, 8.03 mmol) was dissolved in THF (15 mL), and diisopropylethylamine (2.8 mL, 16.06 mmol) was added thereto at - 20°C, and then, a solution obtained by dissolving 3-(2-bromoacetyl)benzonitrile (1.50 g, 6.69 mmol) in THF (5 mL) was slowly added dropwise thereto. After the mixture was stirred for 1 hour under ice-cooling, pivaloyl chloride (2.03 mL, 16.46 mmol) was added thereto, and the mixture was further stirred for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue, ammonium trifluoroacetate (2.70 g, 23.7 mmol) was added under an argon atmosphere, and the mixture was stirred at 140°C for 15 minutes. After the mixture was left to cool to room temperature, water and an aqueous sodium hydrogen carbonate solution were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 99/1 to 25/5) to give the title compound 1 (745 mg, 2.31 mmol, yield: 35%). 1H-NMR (dppm, CDCl3): 8.07-8.03 (m, 1H), 7.97 (dt, J = 6.7, 2.1 Hz, 1H), 7.46-7.38 (m, 2H), 7.17 (s, 1H), 3.87 (d, J = 7.1 Hz, 2H), 1.85-1.70 (m, 6H), 1.47 (s, 9H), 1.28-1.20 (m, 3H), 1.08-1.00 (m, 2H). Mass (m/e): 322 (M+H)+.
  • 36
  • [ 933-20-0 ]
  • [ 3218-02-8 ]
  • [ 1189819-45-1 ]
  • 37
  • [ 390816-44-1 ]
  • [ 3218-02-8 ]
  • [ 1202159-08-7 ]
  • 40
  • [ 55-21-0 ]
  • [ 3309-27-1 ]
  • [ 1122-56-1 ]
  • [ 3218-02-8 ]
  • [ 100-49-2 ]
  • 41
  • [ 1694-31-1 ]
  • [ 1204-21-3 ]
  • [ 3218-02-8 ]
  • 1-cyclohexylmethyl-5-(2,5-dimethoxy-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid [ No CAS ]
  • 42
  • [ 1694-31-1 ]
  • [ 131805-94-2 ]
  • [ 3218-02-8 ]
  • C21H21F6NO2 [ No CAS ]
  • 43
  • [ 615-20-3 ]
  • [ 3218-02-8 ]
  • [ 77414-69-8 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In neat (no solvent) at 20℃; Green chemistry;
88% Stage #1: cyclohexylmethylamine With copper(l) iodide for 0.5h; Stage #2: With potassium hydroxide In water for 1h; Stage #3: 2-chlorobenzo[d][1,3]thiazole With benzyl tri-n-butylammonium bromide In chloroform; water at 20℃; for 6h; chemoselective reaction;
80% With 1H-imidazole; sodium chloride In water for 6h; Reflux; Green chemistry; Synthesis of Benzothiazol-2-yl-morpholine (General Procedure 1) General procedure: In a 50-mL, round-bottom flask, 0.87 g (0.01 mol) of morpholine, 0.68 g(0.01 mol) of imidazole, 0.274 g (0.001 mol) of tributylbenzyl ammonium choride,and 1.69 g (0.01 mol) 2-chlorobenzothiazole were added to 20mL of 5% NaCl (aqueous)solution. The reaction mixture was refluxed for 6 h. The progress of the reactionwas monitored by thin-layer chromatography (TLC). After completion of the reaction,the aqueous layer was washed with ethyl acetate (310 mL). The combinedorganic layer was dried over anhydrous Na2SO4 and concentrated at reduced pressure.Products were purified either by crystallizing or by flash chromatography. Whitecrystalline solid
  • 44
  • [ 303-38-8 ]
  • [ 3218-02-8 ]
  • [ 1332325-16-2 ]
YieldReaction ConditionsOperation in experiment
31% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 6.5h; Inert atmosphere; 5.2.18. N-(4-Fluorobenzyl)-2,3-dihydroxybenzamide (5a) General procedure: A solution of 2,3-dihydroxybenzoic acid (154 mg, 1 mmol), EDCI (380 mg, 2 mmol), DIPEA (2 mmol), and HOBt (290 mg, 2 mmol) in dry THF (15 mL) was stirred at rt under N2. To this solution was added 90% (4-fluorophenyl)methanamine (0.152 mL, 1.2 mmol). The reaction mixture was stirred for 6.5 h at rt. After removal of most of THF, 20 mL of EtOAc was added to the residue. The solution was washed by 1 N HCl, satd NH4Cl and dried over Na2SO4. The concentration provided the residue which was purified by chromatography using petroleum ether/ethyl acetate (1:1) as eluent to give compound 5a as a white solid (51 mg, 57% yield).
  • 45
  • [ 101774-27-0 ]
  • [ 3218-02-8 ]
  • [ 1296202-02-2 ]
  • 47
  • [ 20028-68-6 ]
  • [ 3218-02-8 ]
  • [ 1219456-96-8 ]
  • 48
  • [ 2065-37-4 ]
  • [ 3218-02-8 ]
  • [ 1421609-32-6 ]
YieldReaction ConditionsOperation in experiment
38% In ethanol; 2-((cyclohexylmethyl)amino)naphthalene- 1,4-dione (2g). To a solution of 2-bromo-l,4-napthoquinone (283 mg, 1.2 mmol) in abs EtOH (40 mL) was added an excess of cyclohexanemethylamine (312 uL, 2.4 mmol). Progress of the reaction was monitored with TLC. Compound was purified using chromatography on silica gel to yield 124 mg orange powder (38% yield). ). MS m/z calcd (M+) 270.34, found 270.1. 1H NMR (400 MHz, DMSO-d6) Shift 7.97 (dd, J = 7.03, 17.57 Hz, 2H), 7.83 (dt, J = 1.00, 7.53 Hz, 1H), 7.70 - 7.77 (m, 1H), 7.64 (t, J = 6.15 Hz, 1H), 5.68 (s, 1H), 3.04 (t, J = 6.53 Hz, 2H), 1.50 - 1.81 (m, 6H), 1.05 - 1.32 (m, 3H), 0.81 - 1.03 (m, 2H). C13-HSQC (400 MHz, DMSO-d6) Shift (ppm) 30.82, 25.66, 26.58, 25.66, 30.82, 6.40, 40.14, 48.34, 99.47, 132.52, 135.19, 125.62, 126.34.
  • 49
  • [ 41972-62-7 ]
  • [ 3218-02-8 ]
  • [ 530-62-1 ]
  • [ 1426152-59-1 ]
  • 50
  • [ 21906-31-0 ]
  • [ 3218-02-8 ]
  • [ 1426915-56-1 ]
  • 51
  • [ 21906-31-0 ]
  • [ 3218-02-8 ]
  • C16H22BrN [ No CAS ]
  • 52
  • [ 383132-27-2 ]
  • [ 3218-02-8 ]
  • [ 1432641-94-5 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 4,6-dimethyl-1H-indole-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: cyclohexylmethylamine With triethylamine In dichloromethane at 20℃;
  • 53
  • [ 6307-87-5 ]
  • [ 3218-02-8 ]
  • [ 1445788-75-9 ]
YieldReaction ConditionsOperation in experiment
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate; In hexane; toluene; at 80℃;Inert atmosphere; Microwave irradiation; Sealed tube; Example 7 3-((3-carbamoyl-7-(2,4-dimethoxypyrimidin-5-yl)quinolin-4-yl)amino)-5- ((cvclohexylmethyl)amino)benzoic acid 3-amino-5-[(cvclohexylmethyl)aminolbenzoic acid. Under nitrogen atmosphere in a sealed microwave vial, <strong>[6307-87-5]methyl 3-bromo-5-nitrobenzoate</strong> (250 mg, 0.961 mmol), (aminomethyl)cyclohexane (0.312 mL, 2.403 mmol), cesium carbonate (470 mg, 1.442 mmol), tri-tertbutylphosphine 1 M in hexane (0.096 mL, 0.096 mmol), and palladium(ll) acetate (21.58 mg, 0.096 mmol) in toluene (5 mL) were mixed. The reaction was stirred at 80C overnight, before being concentrated and purified by reverse-phase preparative HPLC ( 30-90% acetonitrile/water + 0.1 % trifluoroacetic acid) to give the intermediate nitro compound. 1H NMR (METHANOLS) d: 7.82 - 7.95 (m, 1 H), 7.43 - 7.58 (m, 2H), 3.94 (s, 3H), 2.99 (d, J = 6.8 Hz, 2H), 1 .88 (d, J = 13.1 Hz, 2H), 1 .75 - 1 .83 (m, 2H), 1.72 (d, J = 10.4 Hz, 1 H), 1.56 - 1.67 (m, 1 H), 1.17 - 1.40 (m, 3H), 0.93 - 1.12 (m, 2H). The intermediate nitro compound, 5% palladium-on-charcoal (102 mg, 0.048 mmol) and methanol (3 ml.) were stirred under hydrogen at room temperature overnight. The catalyst was filtered and 6N sodium hydroxide (0.080 ml_, 0.481 mmol) was added. Upon completion, the mixture was concentrated and taken directly to the next step as-is. LCMS (ES+) m/z 249 [M+H]+.
  • 54
  • [ 615-42-9 ]
  • [ 201230-82-2 ]
  • [ 3218-02-8 ]
  • [ 41763-91-1 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In toluene at 100℃; for 6h; Autoclave; General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalyst General procedure: General procedure carbonylative cyclization ofmethyl-2-iodobenoate/1,2-diiodo benzene for the synthesis ofN-substituted isoindole-1,3-diones using ImmPd-IL as a catalystIn a 100 mL stainless steel autoclave, methyl-2-iodobenoate/1,2-diiodobenzene (1 mmol), aryl amine (2 mmol), ImmPd-IL(2 mol%), toluene (10 mL) and Et3N (2.5 mmol) were added. Theautoclave was closed, purged three times with nitrogen followedwith carbon monoxide, and then pressurized with 1 atm of CO andheated at 100C for 6 h. After completion of reaction the reac-tor was cooled to room temperature, the remaining CO gas wascarefully vented, and the reactor was opened. The reactor vesselwas thoroughly washed with ethyl acetate (10-15 mL) to removeany traces of product and catalyst if present. The catalyst was fil-tered and the reaction mixture was evaporated under vacuum. Theresidue obtained was purified by column chromatography (silicagel, 60-120 mesh; petroleum ether/ethyl acetate, 95:05) to affordthe desired product. The products were confirmed by GC, GC-MS,1H NMR and13C NMR spectroscopic techniques. The purity of com-pounds was determined by GC-MS analysis.
  • 55
  • [ 329-98-6 ]
  • [ 3218-02-8 ]
  • [ 885373-76-2 ]
  • 56
  • [ 51517-01-2 ]
  • [ 3218-02-8 ]
  • [ 1375976-45-6 ]
  • 57
  • [ 1120-82-7 ]
  • [ 3218-02-8 ]
  • [ 1609253-73-7 ]
YieldReaction ConditionsOperation in experiment
80.2% With magnesium sulfate; In dichloromethane; at 20℃; for 72h;Reflux; LA was prepared by a similar procedure as described in the literature [44]. The CH2Cl2 solution (10.0mL) of cyclohexylmethanamine (2.26g, 0.0200mol) was added to CH2Cl2 solution (30.0mL) of <strong>[1120-82-7]1H-1-pyrazolyl-1-methanol</strong> (3.92g, 0.0400mol). The reaction solution was dried over MgSO4 after stirring at room temperature for 3days. The filtrate solvent under reduced pressure to give a colorless and transparent oil product was obtained (4.38g, 80.2%). Anal. Calc. for C15H23N5: C, 65.9, H, 8.48, N, 25.6. Found: C, 65.8, H, 8.62, N, 25.0%. 1H NMR (CDCl3, 400MHz): delta 7.51 (d, 2H, J=1.2Hz, -N=CH-CH=CH-N-), 7.50 (d, 2H, J=2.4Hz, -N=CH-CH=CH-N-), 6.26 (dd, 2H, J=1.2Hz, J=2.0Hz, -=CH-CH=CH-N-), 4.97 (s, 4H, -N-CH2-N-), 2.45 (d, 2H, J=2.8Hz, -C6H11-CH2-N-), 1.72-1.65 (m, 5H, -C6H11-), 1.53-1.50 (m, 1H, ipso-C6H11-), 1.24-1.07 (m, 3H, -C6H11-), 0.81-0.73 (m, 2H, -C6H11-). 13C NMR (CDCl3, 100MHz): delta 140.69 (d, 2C, J=176Hz, -N=CH-CH=CH-N-), 130.92 (d, 2C, J=177Hz, -N=CH-CH=CH-N-), 107.13 (d, 2C, J=185Hz, -N=CH-CH=CH-N-), 68.62 (t, 2C, J=150Hz, -N-CH2-N-), 56.97 (t, 1C, J=132Hz, -C6H11-CH2-N-), 36.64 (d, 1C, J=123Hz, ipso-C6H11-), 31.60 (t, 2C, J=123Hz, o-C6H11-), 27.06 (t, 1C, J=124Hz, p-C6H11-), 26.32 (t, 2C, J=125Hz, m-C6H11-). IR (liquid neat; cm-1): 3110 (w), 2922 (s), 2850 (m), 1512 (m), 1387 (m), 1251 (m), 1124 (w), 1084 (m), 1044 (s), 962 (m), 859 (w), 746 (s), 614 (m).
80.2% In dichloromethane; at 20℃; for 24h; First, cyclohexylmethanamine (2.26 g, 0.0200 mol) was dissolved in a CH2Cl2 solvent (30.0 mL) and <strong>[1120-82-7]1H-1-pyrazolyl-1-methanol</strong> (3.92 g, 0.0400 mol) was dissolved in a CH2Cl2 solvent (20.0 mL) and added. The reaction was carried out at room temperature for 24 hours, the water was removed by solution reaction with MgSO4, and the solution was removed by pressure. A colorless oil was obtained after distillation under reduced pressure. (5.28 g, 80.2%).
  • 58
  • [ 3218-02-8 ]
  • [ 231278-84-5 ]
  • [ 1421356-33-3 ]
YieldReaction ConditionsOperation in experiment
73.5% Stage #1: cyclohexylmethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 24h; 9 Example 9 Preparation of N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-((5-((cyclohexylmethyl)amino)methyl)-2-furyl) -4-quinazolinamine (MS7) Example 9 Preparation of N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-((5-((cyclohexylmethyl)amino)methyl)-2-furyl) -4-quinazolinamine (MS7) Under nitrogen, N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-formyl-2-furyl)-4-quinazolinamine (0.47g, 1mmol) obtained from Example 1 was dissolved in anhydrous tetrahydrofuran (10ml), followed by the addition of cyclohexyl-methylamine (0.23g, 2 mmol), and stirred at room temperature for 6 h. Sodium triacetoxy borohydride (0.42g, 2 mmol) was added, and then the mixture was stirred at room temperature for 24 h. A saturated aqueous solution of sodium carbonate (10 ml) was added, and then the mixure was stirred for 15 min to be layered. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give a yellow solid. The solid was separated by column chromatography on silica gel (200-300 mesh) (eluted with a gradient of ethyl acetate/methanol) to give a yellow solid (0.42g, 73.5%), i.e. the compound of Number MS7. 1H NMR(DMSO-d6)δ: 9.87(s, 1H), 8.74(s, 1H), 8.56(s, 1H), 8.16(d, J=8.3 Hz, 1H), 8.01(d, J=2.6 Hz, 1H), 7.79(d, J=8.8 Hz, 1H), 7.74(m, 1H), 7.46- 7.49(m, 1H), 7.27- 47.35(m, 3H), 7.18(t, 1H), 7.05(d, J=3.2 Hz, 1H), 6.49(d, J=3.3 Hz, 1H), 5.26(s, 2H), 3.99- 4.04(m, 1H), 3.66(s, 2H), 2.51(d, 2H), 1.49- 1.67(m, 11H); ESI-MS m/z: 571[M+H]+.
73.5% Stage #1: cyclohexylmethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 24h; 9 Preparation of N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-((5-((cyclohexylmethyl)amino)methyl)-2-furyl)-4-quinazolinamine (MS7) Example 9 Preparation of N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-((5-((cyclohexylmethyl)amino)methyl)-2-furyl)-4-quinazolinamine (MS7) Under nitrogen, N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-formyl-2-furyl)-4-quinazolinamine (0.47 g, 1 mmol) obtained from Example 1 was dissolved in anhydrous tetrahydrofuran (10 ml), followed by the addition of cyclohexyl-methylamine (0.23 g, 2 mmol), and stirred at room temperature for 6 h. Sodium triacetoxy borohydride (0.42 g, 2 mmol) was added, and then the mixture was stirred at room temperature for 24 h. A saturated aqueous solution of sodium carbonate (10 ml) was added, and then the mixture was stirred for 15 min to be layered. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give a yellow solid. The solid was separated by column chromatography on silica gel (200-300 mesh) (eluted with a gradient of ethyl acetate/methanol) to give a yellow solid (0.42 g, 73.5%), i.e. the compound of Number MS7. 1H NMR (DMSO-d6) δ: 9.87 (s, 1H), 8.74 (s, 1H), 8.56 (s, 1H), 8.16 (d, J=8.3 Hz, 1H), 8.01 (d, J=2.6 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.74 (m, 1H), 7.46-7.49 (m, 1H), 7.27-47.35 (m, 3H), 7.18 (t, 1H), 7.05 (d, J=3.2 Hz, 1H), 6.49 (d, J=3.3 Hz, 1H), 5.26 (s, 2H), 3.99-4.04 (m, 1H), 3.66 (s, 2H), 2.51 (d, 2H), 1.49-1.67 (m, 11H); ESI-MS m/z: 571[M+H]+.
  • 59
  • [ 82437-64-7 ]
  • [ 122-51-0 ]
  • [ 3218-02-8 ]
  • [ 1621968-06-6 ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid; at 160℃;Inert atmosphere; Autoclave; General procedure: To a pressure bottle containing <strong>[82437-64-7]methyl 3-amino-4-phenylthiophene-2-carboxylate</strong> (100 mg, 0.43 mmol), CH(OEt)3 (1 mL) was added, followed by allylamine hydrochloride (93 mg, 0.99 mmol) and AcOH (0.1 mL). The reaction mixture was stirred and refluxed at 160 C overnight. After the reaction, the mixture was evaporated then solidified with ether. The produced white crystals were filtered and dried in vacuo to give the title compound 4-1 (66 mg, 0.25 mmol, 58 % yield): 1HNMR (300 MHz, CDCl3) delta 8.11 (s, 1H), 7.84-7.79 (m, 3H), 7.50-7.44 (m, 2H), 7.41-7.36 (m, 1H), 6.08-5.95 (m, 1H), 5.34-5.24 (m, 2H), 4.72-4.67 (m, 2H); 13C NMR (100 MHz, CDCl3) delta 157.3, 154.3, 147.3, 138.1, 133.7, 131.9, 130.5,128.7, 128.3, 128.0, 124.9, 119.1, 48.0; LC/MS (ESI+): m/z: calcd for C15H12N2OS: 268.34, [M + H]+; found: 269.05
  • 60
  • [ 16590-41-3 ]
  • [ 3218-02-8 ]
  • [ 140-88-5 ]
  • 1'-cyclohexylmethyl-17-cyclopropylmethyl-6,7-didehydro-4,5-epoxy-4',5'-dihydro-3,14-dihydroxy-pyrido[2,3:6,7]morphinan-6(1H)-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: Naltrexone; cyclohexylmethylamine With toluene-4-sulfonic acid In ethanol for 5h; Inert atmosphere; Molecular sieve; Reflux; Stage #2: ethyl acrylate In ethanol for 18h; Inert atmosphere; Molecular sieve; Reflux; Stage #3: With hydrogenchloride In methanol; diethyl ether Inert atmosphere; General procedure General procedure: Naltrexone (0.80 g, 2.35 mmol) was dissolved in 2ml of anhydrous ethanol under a nitrogen atmosphere. Catalytic p-toluene sulfonic acid (10mg) and activated molecular sieves (50 mg) were added. The reaction mixture was stirred for 10min and the appropriate amine (RNH2; 2.35 mmol) was added. The reaction mixture was refluxed for 5 h before adding ethyl acrylate (0.26 ml, 2.35 mmol) and again refluxing for 18h. After completion, the reaction mixture was cooled to room temperature, filtered and washed with dichloromethane (50 ml) and the organic layer was washed with water (2×20 ml) and brine (20 ml). The organic layer was dried over magnesium sulfate, concentrated under reduced pressure to obtain crude product which was purified by flash chromatography using methanol/dichloromethane/ammonium hydroxide (1:98.5:0.5). Yield (20-50%).
  • 61
  • [ 885500-55-0 ]
  • [ 3218-02-8 ]
  • ethyl 4-[(cyclohexylmethyl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 1h;Microwave irradiation; General procedure: 5.1.3 Ethyl 4-(cycloheptylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5c) A mixture of 4 (112 mg, 0.50 mmol), cycloheptanamine (76 muL, 0.60 mmol), and Et3N (209 muL, 1.5 mmol) in NMP (3.0 mL) was heated in a microwave reactor at 180 C for 1 h. After cooling to room temperature, the reaction mixture was quenched with water, extracted with EtOAc, dried over MgSO4, and evaporated in vacuo. The crude mixture was purified by column chromatography on silica gel (CHCl3/MeOH = 100:0 to 90:10) to give the product (135 mg, 90%). 5.1.4 Ethyl 4-[(cyclohexylmethyl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5d) Compound 5d was prepared in 62% yield as a white solid by a method similar to that described for 5c. 1H NMR (DMSO-d6) delta 1.01-1.33 (m, 5H), 1.31 (t, J = 7.1 Hz, 3H), 1.61-1.86 (m, 6H), 3.52 (t, J = 6.1 Hz, 2H), 4.26 (q, J = 7.1 Hz, 2H), 6.66 (d, J = 3.6 Hz, 1H), 7.15 (d, J = 3.6 Hz, 1H), 8.53 (s, 1H), 8.81 (t, J = 5.4 Hz, 1H), 11.67 (br s, 1H); MS (ESI) m/z 302 [M+H]+.
  • 62
  • [ 1201-07-6 ]
  • [ 3218-02-8 ]
  • 8-bromo-N-(cyclohexylmethyl)-2-methyl-4-quinolinamine [ No CAS ]
  • 63
  • [ 1201-07-6 ]
  • [ 3218-02-8 ]
  • 4-[(cyclohexylmethyl)amino]-2-methyl-8-quinolinecarboxamide [ No CAS ]
  • 64
  • [ 6141-13-5 ]
  • [ 3218-02-8 ]
  • [ 1380234-93-4 ]
  • 65
  • [ 3218-02-8 ]
  • [ 4760-34-3 ]
  • [ 2876-08-6 ]
  • [ 106380-62-5 ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 37% With C8H7NO3; copper(ll) bromide In ethanol at 60℃; for 24h; Green chemistry;
  • 66
  • [ 1194-02-1 ]
  • [ 3218-02-8 ]
  • [ 100-49-2 ]
YieldReaction ConditionsOperation in experiment
35%; 63% With water; In aq. phosphate buffer; at 25℃; for 6h;pH 2.7 - 3.2;Electrochemical reaction; General procedure: A conventional two compartment glass or PTFE H-cell separated by a Nafion-117 membrane was used for electrochemical HDF experiments. The cathode was fabricated from a piece of Rh/Ni foam, Rh/Agmesh, Rh/Cu foam, or Rh/carbon felt (projected area: 2 × 3 cm2), whereas the anode was fashioned from a graphite sheet (2 × 3 cm2). 30 mL phosphate buffer solutions (20 mM) served as both the catholyte and the anolyte. Unless otherwise noted, the catholyte was stirred with a stirring velocity of 350 rpm during electrolysis. The concentrations of reactants and their products were determined by an Agilent 7890 A gas chromatograph (GC) and a Waters HPLC system, using standard calibration curves. The fluoride ion (F-) concentration was determined by a REX PHSJ-4F pH/mV meter combined with F- selective electrode (REXPF-202-C). The specific electric energy consumption (SEEC, kW h m-3catholyte) of the HDF process was calculated from the following equation: SEEC I *U*t/1000*V where I is the applied current (A), U is the average cell voltage (3 V), t is HDF time (h), and V is the volume of the catholyte (3 × 10-5 m3). Unless otherwise noted, all of the above-mentioned experimentswere performed under air atmosphere, at 25C.
  • 67
  • [ 773-82-0 ]
  • [ 3218-02-8 ]
  • [ 100-49-2 ]
YieldReaction ConditionsOperation in experiment
33%; 65% With water; In aq. phosphate buffer; at 25℃; for 18h;pH 2.7 - 3.2;Electrochemical reaction; General procedure: A conventional two compartment glass or PTFE H-cell separated by a Nafion-117 membrane was used for electrochemical HDF experiments. The cathode was fabricated from a piece of Rh/Ni foam, Rh/Agmesh, Rh/Cu foam, or Rh/carbon felt (projected area: 2 × 3 cm2), whereas the anode was fashioned from a graphite sheet (2 × 3 cm2). 30 mL phosphate buffer solutions (20 mM) served as both the catholyte and the anolyte. Unless otherwise noted, the catholyte was stirred with a stirring velocity of 350 rpm during electrolysis. The concentrations of reactants and their products were determined by an Agilent 7890 A gas chromatograph (GC) and a Waters HPLC system, using standard calibration curves. The fluoride ion (F-) concentration was determined by a REX PHSJ-4F pH/mV meter combined with F- selective electrode (REXPF-202-C). The specific electric energy consumption (SEEC, kW h m-3catholyte) of the HDF process was calculated from the following equation: SEEC I *U*t/1000*V where I is the applied current (A), U is the average cell voltage (3 V), t is HDF time (h), and V is the volume of the catholyte (3 × 10-5 m3). Unless otherwise noted, all of the above-mentioned experimentswere performed under air atmosphere, at 25C.
  • 68
  • [ 3218-02-8 ]
  • [ 18480-53-0 ]
  • 3,4-dichloro-N-(cyclohexylmethyl)isothiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% 1.1. Synthesis of 3,4-dichloro-N-(cyclohexylmethyl)isothiazole-5-carboxamide: 730 mg of <strong>[18480-53-0]3,4-dichloroisothiazole-5-carboxylic acid</strong> (3.7 mmol) were dissolved in 10 ml of dichloromethane and a drop of dimethylformamide was added. 1.4 g of oxalyl chloride (11.1 - - mmol) were added dropwise at room temperature. After stirring for 1 h at room temperature, the solution was evaporated to dryness on a rotary evaporator. The residue was taken up in 3 ml of dichloromethane and slowly added dropwise to a solution of 626 mg of 1 - cyclohexylmethanamine (5.5 mmol) and 746 mg of triethylamine (7.4 mmol) in 10 ml of dichloromethane. The mixture was stirred at room temperature for 1 h. The reaction mixture was then added to water and extracted repeatedly with dichloromethane. The concentrated extracts were dried over MgS04, concentrated and purified by column chromatography. Yield: 1.05 g (97percent of theory).'H-NMR (400 MHz, CDC13delta, ppm) 6.86 (br,lH), 3.34 (tr,2H), 1.77 (m,4H), 1.66 (m,lH), 1.58 (m,lH), 1.3-1.15 (m,3H), 1.0 (m,2H).
97% 730mg of <strong>[18480-53-0]3,4-dichloroisothiazole-5-carboxylic acid</strong> (3.7 mmol) were dissolved in 10 ml of dichloromethane and a drop of dimethylformamide was added. 1.4 g of oxalyl chloride (11.1 mmol) were added dropwise at room temperature. After stirring for 1 h at room temperature, the solution was evaporated to dryness on a rotary evaporator. The residue was taken up in 3 ml ofdichloromethane and slowly added dropwise to a solution of 626 mg of 1- cyclohexylmethanamine (5.5 mmol) and 746 mg of triethylamine (7.4 mmol) in 10 ml of dichloromethane. The mixture was stirred at room temperature for 1 h. The reaction mixture was then added to water and extracted repeatedly with dichloromethane. The concentrated extracts were dried over MgSO4, concentrated and purified by column chromatography. Yield:1.05 g (97percent of theory).?H-NMR (400 MHz, CDC13 , ppm) 6.86 (br, 1H), 3.34 (tr, 2H), 1.77 (m, 4H), 1.66 (m, 1H), 1.58 (m, 1H), 1.3-1.15 (m, 3H), 1.0 (m, 2H).
  • 69
  • [ 16523-31-2 ]
  • [ 3218-02-8 ]
  • (6Z)-4-(hexahydrobenzylamino)-6-(hexahydrobenzyliminio)-3-oxocyclohexa-1,4-dien-1-olate [ No CAS ]
  • 70
  • [ 3218-02-8 ]
  • [ 123577-99-1 ]
  • C15H21F2N [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.4 g A solution of commercial <strong>[123577-99-1]1-(3,5-difluorophenyl)ethanone</strong> (5 g, 32 mmoles) and cyclohexanemethylamine (3.6 g, 32 mmoles) in toluene (50 mL) is heated for 40 hours at reflux in an azeotropic assembly. The toluene is evaporated off and the residue is dissolved in ethanol (40 mL). The solution is cooled to 10 C., and then NaBH4 (1.2 g, 32 mmoles) is added in portions; the reaction mixture is stirred for 2 hours, and NaBH4 (0.12 g) is again added. After stirring for 30 minutes, a 3N aqueous HCl solution is added carefully, and the ethanol is evaporated off in vacuo. The residue is taken up in toluene (200 mL) and washed with a 40% aqueous NaOH solution. The organic phase is dried over MgSO4, and evaporation under reduced pressure yields intermediate 705 (4.4 g), which is used without additional treatment in the following step.1H NMR (300 MHz, DMSO-d6): delta 7.00 (m, 3H), 3.70 (quad, 1H), 2.20 (dd, 1H), 2.05 (dd, 1H), 1.80-1.70 (3m, 10H), 1.30 (m, 1H), 1.20 (d, 3H) IR (cm-1): 2922-2850, 1114
  • 71
  • [ 579514-75-3 ]
  • [ 3218-02-8 ]
  • C18H26N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; General procedure: To a solution fo <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (560 mg, 2.3 mmol) in 20mL of EtOH were added butan-1-amine (853 mg, 11.6 mmol) and stirred at rt for 2 h.The reaction mixture was concentrated to dryness, and the residue was dissolved inEtOAc (10 x 3 mL) and washed with brine (10 mL). The combined organic layerswere dried over MgSO4, and concentrated in vacuo to afford the product tert-butyl 4-(butylamino)-3-nitrobenzoate (35b) as yellow-orange solid (490 g, 72% yield).
  • 72
  • [ 107-94-8 ]
  • [ 593-75-9 ]
  • [ 74965-38-1 ]
  • [ 3218-02-8 ]
  • C24H36ClN3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; for 24h; General procedure: Into a clear solution of 2-(Boc-amino)benzaldehyde 1 (1 mmol) in methanol (5 mL) was added amine 2 (1 mmol) and stirred for 5 minutes at room temperature. Then, 3-chloropropanoic acid (3, 1 mmol) and methylisocyanide (4, 1 mmol) were added to the reaction pot. The reaction was allowed to stir until no noticeable amounts of starting material were visible using TLC. Upon completion ofthe reaction, methanol was evaporated under reduced pressure and the crude Ugi products, without any purification, was dissolved in a CH2Cl2 and trifluoroacetic acid mixture(1:1, 2 mL). The reaction was then allowed to stir at room temperature for 5 h and monitored by TLC. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the crude compound, without any purification, was dissolvedin acetonitrile (2 mL) and K2CO3 (2 mmol) was added. The reaction was then allowed to stir under refluxing conditions for 1 h and reaction completion was monitored usingTLC. The reaction mixture was then allowed to cool to room temperature and the solvent evaporated under reduced pressure. The crude products were subjected to flash column chromatography (EtOAc/hexanes) to yield pure compounds 8a-j.
  • 73
  • C18H21NO [ No CAS ]
  • [ 1096-84-0 ]
  • [ 3218-02-8 ]
  • 74
  • C18H23NO [ No CAS ]
  • [ 1096-84-0 ]
  • [ 3218-02-8 ]
  • 75
  • [ 14418-84-9 ]
  • [ 3218-02-8 ]
  • N-(cyclohexylmethyl)prop-2-ene-1-sulfonamide [ No CAS ]
  • 76
  • [ 3218-02-8 ]
  • [ 886762-70-5 ]
  • C13H17BrN2O2 [ No CAS ]
  • 77
  • [ 1882-71-9 ]
  • [ 3218-02-8 ]
  • 2-cyclohexyl-6-methoxyquinazolin-4(3H)-one [ No CAS ]
  • 78
  • [ 51940-64-8 ]
  • [ 3218-02-8 ]
  • ethyl 2-chloro-4-(cyclohexylmethylamino)pyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃; for 1h; A solution of <strong>[51940-64-8]ethyl 2,4-dichloropyrimidine-5-carboxylate</strong> 1 (5.00 g, 22.7 mmol) in acetonitrile (100 mL) was mixed with diisopropyl ethyl amine (3.95 mL, 22.7 mmol) and cyclohexylmethanamine (2.0, 2.95 mL, 22.7 mmol) at 0C. The reaction mixture was stirred at room temperature for 1 h, then diluted with water (50.0 mL) and extracted with EtOAC (250.0 mL). The combined organic layers were dried over NaSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (ethyl acetate-hexane) to afford compound 3. Yield 86%, mp 156-158C. 1H NMR spectrum, delta, ppm: 8.63 s (1H), 8.45 br.s (1H), 4.36 q (2H, J = 7.2 Hz), 3.39 t (2H, J = 6.4 Hz), 1.80- 1.57 m (6H), 1.39 t (3H, J = 6.8 Hz), 1.28-1.19 m (3H), 1.07-0.97 m (2H). 13C NMR spectrum, delta, ppm: 166.3, 163.8, 162.0, 160.2, 103.6, 61.34, 46.95, 37.55, 30.80, 26.28, 25.77, 14.15. MS (MM): m/z: 298.0 [M + H]+. Found, %: C 56.37; H 6.68; N 14.20. C14H2OClN3O2. Calculated, %: C 56.47; H 6.77; N 14.11.
  • 79
  • [ 3622-04-6 ]
  • [ 3218-02-8 ]
  • N-(cyclohexylmethyl)benzo[d]thiazole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.5% General procedure: To a magnetically stirred suspension of the carboxylic acid 4b(1.6 mmol) in anhydrous DCM were successively added tributylamine(Hunig's base) (6 equiv.) and N,N,N0,N0-Tetramethyl-O-(1Hbenzotriazol-1-yl)uroniumhexafluorophosphate (HBTU) (1.2equiv.) and the mixturewas allowed to stir at room temperature for30 min. The appropriate amine (1.2 equiv.) was then added, and thesolution was stirred at room temperature for 4e5 h. The solventwas then evaporated under reduced pressure and the resultingcrude product was dissolved in EtOAc, washed with aqueousNaHCO3 solution, 1 N HCl and brine, dried over anhydrous MgSO4and concentrated to give a crude resin. The crude product wasfurther purified using column chromatography. N-(cyclohexylmethyl)benzo[d]thiazole-2-carboxamide (4c).Prepared from cyclohexylmethyl amine. Column chromatographyon silica gel (DCM:Hexane, 6.5:3.5) afforded 4c as a white solid(91.5%); mp: 106e107 C; 1H NMR (d): (400 MHz, CDCl3) d 8.06 (dd,J 7.6, 0.7 Hz, 1H), 7.99e7.94 (m, 1H), 7.57e7.45 (m, 3H), 3.35 (t,J 6.6 Hz, 2H), 1.89e1.71 (m, 4H), 1.72e1.58 (m, 2H), 1.34e1.18 (m,3H), 1.09e0.97 (m, 2H); 13C NMR (d): (101 MHz, CDCl3) d 164.43,160.03, 153.04, 137.28, 126.88, 126.73, 124.33, 122.55, 46.17, 38.20,31.00, 26.48, 25.94; MS (ESI): m/z 275.07 [M H]
  • 80
  • [ 728034-12-6 ]
  • [ 3218-02-8 ]
  • [ 165806-95-1 ]
  • 4-(1-(cyclohexylmethyl)-4-(4-fluorophenyl)imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used
  • 81
  • [ 2745-26-8 ]
  • [ 3218-02-8 ]
  • C13H19NO2 [ No CAS ]
  • 82
  • [ 3218-02-8 ]
  • [ 1074-68-6 ]
  • N-(cyclohexylmethyl)-1-(2-(methylsulfanyl)pyrimidin-4-yl)methanimine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium hydroxide In dichloromethane at 20℃; A/-(Cyclohexylmethyl)-1 -(2-(methylsulfanyl)pyrimidin-4-yl)methanimine (7) Cyclohexylmethylamine (356 mI_, 2.74 mmol) and K2CO3 (0.227 g, 1 .64 mmol) were added to a solution of the crude aldehyde 1 (0.21 1 g, 1 .37 mmol) in CH2CI2 (5 ml_). The reaction mixture was stirred at r.t. overnight. 1 H NMR analysis indicated complete consumption of the aldehyde. The reaction mixture containing the imine was used directly in the next step without isolation.
  • 83
  • [ 141-97-9 ]
  • [ 3218-02-8 ]
  • [ 456-04-2 ]
  • ethyl 1-(cyclohexylmethyl)-5-(4-fluorophenyl)-2-methyl-1H-pyrrole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: ethyl acetoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0℃; for 0.5h; Stage #2: 2-Chloro-4'-fluoroacetophenone With potassium iodide In tetrahydrofuran; paraffin oil at 20℃; for 2h; Stage #3: cyclohexylmethylamine In acetic acid at 80℃; for 18h;
  • 84
  • [ 3218-02-8 ]
  • [ 76-05-1 ]
  • [ 849475-89-4 ]
  • (x)C2HF3O2*C17H20N4O3 [ No CAS ]
  • 85
  • [ 331-39-5 ]
  • [ 3218-02-8 ]
  • N-(cyclohexylmethyl)-3-(3,4-dihydroxyphenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With HBTU; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; N-(cyclohexylmethyl)-3-(3,4-dihydroxyphenyl)acrylamide General procedure: To a mixture of the caffeic acid (1 mmol) in dry THF (4 mL) was added HOBt (1.2 mmol), HBTU (1.2 mmol) and DIEA (1.5 mmol). The reaction mixture was stirred at room temperature. The reaction was terminated when the caffeic acid was finished by TLC control. Purified by column chromatography.
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