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[ CAS No. 37394-93-7 ] {[proInfo.proName]}

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Chemical Structure| 37394-93-7
Chemical Structure| 37394-93-7
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Product Details of [ 37394-93-7 ]

CAS No. :37394-93-7 MDL No. :MFCD00018894
Formula : C9H10ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :LPMANECYGPQBOX-UHFFFAOYSA-N
M.W : 183.63 Pubchem ID :101479
Synonyms :

Calculated chemistry of [ 37394-93-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.52
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 2.15
Log Po/w (SILICOS-IT) : 2.35
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.54 mg/ml ; 0.00838 mol/l
Class : Soluble
Log S (Ali) : -1.69
Solubility : 3.77 mg/ml ; 0.0205 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0287 mg/ml ; 0.000156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 37394-93-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37394-93-7 ]

* 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 [ 37394-93-7 ]

[ 37394-93-7 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 79-04-9 ]
  • [ 95-53-4 ]
  • [ 37394-93-7 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; In dichloromethane; water; for 18h; The procedure described in Example 16A was followed, substituting 2-methylaniline for 3,5-dimethylaniline to provide the title compound (90% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) ? 2.20 (s, 3H), 4.30 (s, 2H), 7.16 (m, 3H), 7.38 (d, 1H, J=7.8 Hz), 9.63 (br s, 1H); MS (DCI/NH3) m/e 184 (M+H)+.
83.1% at 0 - 25℃; for 2.5h; General procedure: To a solution of 4a-j (0.11 mol) in AcOH (30 mL) was added dropwise chloroacetyl chloride (9.5 mL, 0.12 mol) at 0C. The mixture was allowed to react at 0C for 0.5 h, and at room temperature for 2 h. AcONa solution was added to the reaction, and the precipitated white solid was collected and dried to afford 5a-j.
82% With potassium carbonate; In acetone;Reflux; General procedure: Chloroacetyl chloride (0.06 mol) was added dropwise toa mixture of the appropriate amine (0.05 mol) and K2CO3(0.06 mol) in acetone (50 ml) at room temperature. Thereaction mass was refluxed for 4-8 h, and then progress of reaction was monitored by TLC using ethyl acetate-hexane(8:2) solvent system as eluent. Then the reaction mixture was cooled and poured into 100 ml of ice water. The resulting white precipitates were filtered off and dried under the vacuum condition and purified by recrystallization from alcohol. Similarly, other compounds (5a-5j) were prepared by using various substituted amines.
76.7% In benzene; at 0℃; A solutionof 1 mL (9.32 mmol) of o-toluidine in 10 mL of anhydrous benzene (dried over metallic sodium) wasc ooled to 0C, and 1.11 mL (14.0 mmol) of chloroacetyl chloride was added. A white solid immediately precipitated. The mixture was evaporated, and the precipitate was washed with water until neutral washings and dried. Yield 1.31 g (76.7%), colorless crystals, mp 111-113C; published data [13]: mp 102-104C; Rf 0.57 (benzene-EtOAc, 9 : 1). HPLC: 0-3 min, 100% A; 3-20 min, 0 to 100% B; 20-22 min, 60% B; tau = 20.77 min. 1H NMR spectrum, delta, ppm: 2.20 s (3H,CH3), 4.30 s (1H, CH2), 7.10 d (1H, Harom, J = 7.3 Hz), 7.15 d (1H, Harom, J = 7.5 Hz), 7.20 d (1H, Harom,J = 7.4 Hz), 7.40 d (1H, Harom, J = 7.8 Hz), 9.65 s(1H, NH). Found, %: C 58.86; H 5.48; N 7.65;Cl 19.22. C9H10ClNO. Calculated, %: C 58.86; H 5.49;N 7.63; Cl 19.31.
68% General procedure: To a solution of substituted aniline (compounds 1a-1t) or 5-aminoindole and 6-aminoquinoline (1.0 equiv.) in dichloromethane (CH2Cl2) (15mL) at 0C, potassium carbonate (K2CO3) (2.0 equiv.) was added. The reaction was stirred at 0C for 15min. Into this stirring solution, chloroacetyl chloride (1.0 equiv.) was added dropwise at 0C. The mixture was stirred for 2hat room temperature. After completion of the reaction, water (20mL) was added, and the mixture was extracted with dichloromethane. The organic solvent phase was concentrated under vacuum to afford the desired compounds 2a-2t, 5a and 5b. 4.1.1.1 2-Chloro-N-(2-methylphenyl)acetamide (2a) White powder, 68% yield. 1H NMR (DMSO-d6, 500MHz): delta 9.65 (bs, 1H), 7.38 (d, J=7.5Hz, 1H), 7.23 (d, J=7.5Hz, 1H), 7.19-7.17 (m, 1H), 7.13 (dd, J1=7.5Hz, J2=1.0Hz, 1H), 4.30 (bs, 2H), 2.20 (s, 3H).
49% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h; General procedure: The desired compounds (5-19) were obtained following aprocedure previously reported by us.21Particularly, chloroacetyl chloride (78 ll, 1 mmol) and N,Ndiisopropylethylamine(175 ll, 1 mmol) were added dropwise to a solution of the appropriate substituted anilines in DCM (5 mL).The mixture was stirred for 1 h at room temperature. Successively,the reaction was quenched with a saturated NaHCO3 aqueous solution(5 mL). The reaction mixture was extracted with EtOAc (3 10 mL), dried over Na2SO4 and evaporated under reduced pressure.The residue was crystallized from EtOH or Et2O.
In acetonitrile;Reflux; a) was reacted in MeCN with chloroacetyl chloride at reflux to give b) which was then reacted with 2-chloro-lH- benzimidazole in K2CO3, DMF to give d) . d) was then reacted with NH2NH2*H20 in EtOH to give e) that, reacted w i th 2-chloro-l- (1, 3-dihydro-2H-isoindol-2-yl) ethanone, lead to the obtainment of the desired 3- [ [2- (2, 3-dihydro- lH-indol-l-yl) -2-oxoethyl] thio] -N- (2-methylphenyl) -9H- 1, 2, 4-Triazol [4, 3-a] benzimidazole- 9-acetamide .
In acetonitrile;Reflux; a) was reacted in MeCN with chloroacetyl chloride at reflux to give b) which was then reacted with 2-chloro-1H-benzimidazole in K2CO3, DMF to give d). d) was then reacted with NH2NH2*H2O in EtOH to give e) that, reacted with 2-chloro-1-(1,3-dihydro-2H-isoindol-2-yl)ethanone, lead to the obtainment of the desired 3-[[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]thio]-N-(2-methylphenyl)-9H-1,2,4-Triazol[4,3-a]benzimidazole-9-acetamide.
With pyridine; In water; at 0℃; for 1h; General procedure: Generalprocedure: To a solution of aniline or benzylamine (10 mmol) inwater (20 ml) and pyridine (1.6 ml) was added chloracetyl chloride(1.69 g, 15 mmol) slowly at 0 C. The reaction mixture was stirredat 0 C for 1.0 h and then diluted with water (50 ml). The precipitatewas collected by filtration, washed with water and dried undervacuum. N-substituted-2-chloroacetamides 3a-3r were obtainedas solid (yield 50-80%).
With triethylamine; In dichloromethane; at 20℃; for 0.5h; General procedure: To a solution of the appropriate amine (50 mmol) in triethylamine (5.1 mg, 50.5 mmol) and dichloromethane (50 mL), chloroacetyl chloride (70 mmol) was added dropwise, and the mixture was allowed to stir at room temperature for 30 min. Then, it was slowly poured into a saturated solution of NaHCO3 (100 mL). The layers were separated, and the aqueous layer was extracted with CH2-Cl2 (30 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The product was dried and recrystallized from ethyl acetate andpetroleum ether to obtain 2-chloro-N-substituted acetamides. The properties and analytical data for these compounds 15a-v were listed in the supporting information.
General procedure: Under nitrogen atmosphere, dry CH2Cl2 (30 mL), amine (0.02 mol), and Et3N (0.05 mol) wereadded to a three-necked round bottom ask and stirred for 0.5 h, then chloroacetyl chloride droppedslowly and reacted for 3 h at room temperature. Then, the solution was washed with 2 mol L1hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively,then dried over anhydrous Na2SO4 and filtered. After evaporating CH2Cl2 in vacuum, the obtainedcrude product was rened by recrystallization using ethyl acetate/petroleum ether.
In acetic acid; at 0 - 20℃; General procedure: Various substituted anilines were dissolved in glacial acetic acidat 0 C, to this was added over 30 min choloroacetylchloride (2equivalents). The reaction mixture was brought to room temperatureand stirred overnight. Saturated sodium bicarbonate solutionwas added till complete neutralization. The resulting precipitatewas filtered off and washed with n-hexane and dried. The resultantproduct was used further without any purification. Either of 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, vanillin or isovanillin(1 equivalent) was dissolved in acetone and potassiumcarbonate (2 equivalents) was added. Then correspondingsubstituted acetamide was mixed to the stirring solution. Finally,potassium iodide (1.5 equivalent) was added. The reaction mixturewas refluxed for 8-10 h. After completion of reaction, the resultantmixture was concentrated and treated with water and extractedwith ethyl acetate (3 x 20 mL). The organic layers were combinedand treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel(60-120) using petroleum ether: ethyl acetate (9:1).
With acetic acid; at 0 - 20℃; General procedure: Various substituted anilines were dissolved in glacial acetic acid at0 C, to this was added over 30 min choloroacetyl chloride (2 equivalents).The reaction mixture was brought to room temperature andstirred overnight. Saturated sodium bicarbonate solution was added tillcomplete neutralization. The resulting precipitate was filtered off andwashed with n-hexane and dried. The resultant product (1) was usedfurther without any purification. Either of 4-hydroxy benzaldehyde(2a), vanillin (2b) or isovanillin (2c) (1 equivalent) was dissolved inacetone and potassium carbonate (2 equivalents) was added. Thencorresponding substituted acetamide (1) was mixed to the stirring solution.Finally, potassium iodide (1.5 equivalent) was added. The reactionmixture was refluxed for 8-10 h. After completion of reaction,the resultant mixture was concentrated and treated with water andextracted with ethyl acetate (3×20 mL). The organic layers werecombined and treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel (60-120)using petroleum ether: ethyl acetate (9:1).
With triethylamine; at 0 - 20℃; for 4h; General procedure: In a round bottom flask, primary or secondary amines (0.1 mol) and triethyl amine weredissolved in DCM and stirred at 0 C. 2-Chloroacetyl chloride (0.1 mol) was added to reaction mixture drop wise with continuous stirring on magnetic stirrer. After the addition,the ice bath was removed and the reaction mixture was stirred at room temperature for 4 h.The progress of the reaction was monitored by TLC using ethyl acetate: hexane (1:9) as asolvent system. After completion of the reaction, the reaction mixture was poured on crushedice and neutralised by adding acetic acid to it. The obtained solid intermediates of respectiveamines were filtered, dried and crystallised in ethanol.

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  • 2
  • [ 37394-93-7 ]
  • [ 145133-90-0 ]
YieldReaction ConditionsOperation in experiment
60% With ammonium hydroxide; at 60℃; for 6h;Inert atmosphere; General procedure: To a solution of substituted phenyl acetamide, 2a-2t or 5a or 5b (0.25g, 1.0 equiv) excess of liquid ammonia (NH3) (10mL) was added, and the reaction was heated at 60C for 6h. The reaction mixture was allowed to cool to room temperature, after which 30mL of ethyl acetate was added and the organic layer was separated and dried over anhydrous Na2SO4, and concentrated in vacuo, which provided the free amine of compounds 3a-3t, 6a, and 6b as a solid/oily product with 50-60% yield. Purification of the crude products was done by column chromatography using DCM:MeOH (9.5:0.5) as eluents to afford the aforementioned compounds.4.1.2.1 2-amino-N-(o-tolyl)acetamide (3a) White oily product, 60% yield. 1H NMR (DMSO-d6, 500MHz) delta 9.75 (bs, 1H), 7.39-7.44 (m, 2H), 7.10 (t, J=7.5Hz, 1H), 6.82 (d, J=7.0Hz, 1H), 3.23 (s, 2H), 2.24 (s, 3H).
  • 3
  • [ 37394-93-7 ]
  • [ 116433-48-8 ]
YieldReaction ConditionsOperation in experiment
With sodium azide; In water; N,N-dimethyl-formamide; at 100℃; for 6h; General procedure: The freshly synthesized above intermediates were heated at 100 C with sodium azide (0.1mol) in DMF-H2O for 6 h. The progress of the reaction was monitored by TLC using ethylacetate: hexane (1:9) as a solvent system. The reaction mixture was poured on crushed ice.Ethyl acetate was added to the mixture and the organic layer was separated. The organiclayers were dried over MgSO4 and solvent was removed under reduced pressure. All theazides (2a-r) were synthesized from respective amines, were obtained as solid compoundsexcept azide (2e) obtained from o-anisidine in liquid state. This azide (2e) was extracted inorganic layer using ethyl acetate and solvent is removed under reduced pressure. After this itwas used for further reaction without any purification. All the newly synthesized solid azideswere crystallised in ethanol and then used for further reaction.[
  • 4
  • [ 37394-93-7 ]
  • [ 73663-82-8 ]
YieldReaction ConditionsOperation in experiment
91.2% With potassium iodide; In acetone; at 60℃; for 2h; General procedure: A mixture of 5a-j (18 mmol) and KI (4.4 g, 27 mmol) inacetone (40 mL) was refluxed for 2 h, and the solvent was evaporated in vacuo. Water was added, and the solids were collected and dried to give compounds 6a-j.
  • 5
  • [ 34803-66-2 ]
  • [ 37394-93-7 ]
  • N-(2-methylphenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With sodium carbonate; In DMF (N,N-dimethyl-formamide); water; at 20℃; for 18h; [1578] A mixture of 1-pyridin-2-ylpiperazine (24 mg, 0.15 mmol, Aldrich), N-(2-methyl-phenyl)-2-chloroacetamide (37 mg, 0.20 mmol, Maybridge) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure and the residue purified by preparative HPLC to provide 29.3 mg (63%) of the desired product. 1H NMR (500 MHz, DMSO-d6) delta2.23 (s, 3H), 2.62 (t, J=4 Hz, 4H), 3.20 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.05 (t, J=6 Hz, 1H), 7.10 (m, 2H), 7.58 (t, J=5 Hz, 1H), 7.78 (d, J=6 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 9.40 (s, 1H); MS (ESI/APCI+) m/e 311 (M+H)+
29.3 mg (63%) With sodium carbonate; In water; N,N-dimethyl-formamide; EXAMPLE 184 N-(2-methylphenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide A mixture of 1-pyridin-2-ylpiperazine (24 mg, 0.15 mmol, Aldrich), N-(2-methyl-phenyl)-2-chloroacetamide (37 mg, 0.20 mmol, Maybridge) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure and the residue purified by preparative HPLC to provide 29.3 mg (63%) of the desired product. 1H NMR (500 MHz, DMSO-d6) delta2.23 (s, 3H), 2.62 (t, J=4 Hz, 4H), 3.20 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.05 (t, J=6 Hz, 1H), 7.10 (m, 2H), 7.58 (t, J=5 Hz, 1H), 7.78 (d, J=6 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 9.40 (s, 1H); MS (ESI/APCI+) m/e 311 (M+H)+.
  • 6
  • [ 23003-30-7 ]
  • [ 37394-93-7 ]
  • [ 1134193-68-2 ]
  • 7
  • [ 1383787-17-4 ]
  • [ 37394-93-7 ]
  • [ 1383787-05-0 ]
YieldReaction ConditionsOperation in experiment
68.5% With potassium carbonate; In acetone; at 20℃; for 2h; General procedure: Compound 4a (0.15 g, 0.5 mmol), K2CO3 (0.14 g, 1.0 mmol), from different 2-chloro-N-(substituted aromatic group)acetamides (0.05 mmol), was dissolved in acetone (10 mL).28 The reaction mixture was stirred at ambient temperature for 2 h and then evaporated under reduced pressure. The residue was dissovled with a small amount CH2Cl2 and chromatographed on silica gel using ethyl acetate-petroleum ether system. Pure fractions were collected and concentrated, giving the desired compounds 5a1-5a16.
  • 8
  • [ 717-00-0 ]
  • [ 37394-93-7 ]
  • [ 1088200-72-9 ]
YieldReaction ConditionsOperation in experiment
84% General procedure: A suspension of 7.42 mmol of 1-benzyluracil1 14, 1-benzylthymine or 1-(diphenylmethyl)uracil and K2CO3 (1.6 g, 11.58 mmol) in 15 mL of DMF was stirred at 80 ? for 1 h then cooled to rt. After addition of 2-chloroacetanilide 1-5 (7.66 mmol), the reaction mixture was stirred for 2 h, chilled overnight, filtered and the solvent removed under reduced pressure. The residue was treated with 50 mL of water, and the resulting precipitate filtered and recrystallized from a mixture of acetone-iPrOH-DMF.
  • 9
  • [ 37052-78-1 ]
  • [ 37394-93-7 ]
  • [ 356587-79-6 ]
  • 10
  • 4-(4-hydroxybenzylidene)-1-(3-methoxyphenyl)-2-phenyl-1H-imidazol-5(4H)-one [ No CAS ]
  • [ 37394-93-7 ]
  • 2-(4-((1-(3-methoxyphenyl)-5-oxo-2-phenyl-1,5-dihydro-4H-imidazol-4-ylidene)methyl)phenoxy)-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% General procedure: Potassium carbonate (10 mmol, 1.38 g) was added to a solution of compound 3 or 4 (10 mmol, 3.70 g) in dry DMF (15 mL) and stirred at room temperature for 0.5 h. Then, the appropriate 2-chloro-N-un/substituted phenylacetamide 5a-j (10 mmol) was added and heated at 100 C for 8 h. The reaction mixture was poured onto ice/water and the precipitated solid was filtered off, washed with water, dried and crystallized from ethanol.
  • 11
  • 4-(4-hydroxybenzylidene)-1-(4-methoxyphenyl)-2-phenyl-1H-imidazol-5(4H)-one [ No CAS ]
  • [ 37394-93-7 ]
  • 2-(4-((1-(4-methoxyphenyl)-5-oxo-2-phenyl-1,5-dihydro-4H-imidazol-4-ylidene)methyl)phenoxy)-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General procedure: Potassium carbonate (10 mmol, 1.38 g) was added to a solution of compound 3 or 4 (10 mmol, 3.70 g) in dry DMF (15 mL) and stirred at room temperature for 0.5 h. Then, the appropriate 2-chloro-N-un/substituted phenylacetamide 5a-j (10 mmol) was added and heated at 100 C for 8 h. The reaction mixture was poured onto ice/water and the precipitated solid was filtered off, washed with water, dried and crystallized from ethanol.
  • 12
  • [ 37394-93-7 ]
  • [ 57644-24-3 ]
  • C23H18ClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% General procedure: To the appropriate Schiff bases of isatin (10 mmol) in8-10 cm3 of anhydrous DMF, K2CO3 (15 mmol) was addedand stirred at room temperature for 1 h. After completion of1 h, the solution turned red brown in color. Appropriatechloroanilides (10 mmol) and KI (2 mmol) were then addedto this solution drop wise and heated at 60 C for 5.5-9 h.After conforming the end of reaction by TLC (ethyl acetate:n-hexane 30:70), the mixture was poured into ice cold water.Precipitated crude product was filtered and washed thoroughlywith cold water (3 9 200 cm3). Compounds wererecrystallized from ethanol/water mixture (1:1). Reactiontimes, melting points, and yields are depicted in Table 1.
  • 13
  • C16H14N2O [ No CAS ]
  • [ 37394-93-7 ]
  • 2-[3-(2,5-dimethylphenylimino)-2-oxoindolin-1-yl]-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: To the appropriate Schiff bases of isatin (10 mmol) in8-10 cm3 of anhydrous DMF, K2CO3 (15 mmol) was addedand stirred at room temperature for 1 h. After completion of1 h, the solution turned red brown in color. Appropriatechloroanilides (10 mmol) and KI (2 mmol) were then addedto this solution drop wise and heated at 60 C for 5.5-9 h.After conforming the end of reaction by TLC (ethyl acetate:n-hexane 30:70), the mixture was poured into ice cold water.Precipitated crude product was filtered and washed thoroughlywith cold water (3 9 200 cm3). Compounds wererecrystallized from ethanol/water mixture (1:1). Reactiontimes, melting points, and yields are depicted in Table 1.
  • 14
  • [ 3790-45-2 ]
  • [ 37394-93-7 ]
  • 2-(3,4-dihydro-1-phenyl-1H-pyrido[3,4-b]indol-2(9H)-yl)-N-o-tolylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% General procedure: To a stirred solution of 3 (0.47g, 2mmol) in dry DMF (3mL), K2CO3 (0.83g, 6mmol) was added and stirred the reaction mixture at room temperature for 30min. Thereafter, 2-Chloro-N-phenylacetamide 6a (0.34g, 2mmol) was added and the reaction mixture was stirred for additional 3h at room temperature. On completion of the reaction as monitored by TLC, the contents were poured into ice water (50mL) whilst stirring with a glass rod. Thereafter, the aqueous layer was extracted with EtOAc (3×20mL). The organic layers were combined and washed with brine (40mL), dried with anhydrous Na2SO4 and concentrated to yield the product (0.59g from 0.47g, 78%). For analytical grade, the compound was passed through short silica gel (100-200 mesh) column chromatography (ethylacetate: hexane=6:4, Rf 0.40) to get 7a as a white solid.
  • 15
  • [ 2349-67-9 ]
  • [ 37394-93-7 ]
  • 2-amino-5-[(2-methylphenylcarbamoyl)methylthio]-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; In ethanol; water; at 20℃; General procedure: A solution of sodium hydroxide (6 mmol) in water (20 mL) was added to a mixture of 2-amino-5-mercapto-1,3,4-thiadiazole (6 mmol), appropriate 2-chloro-N-(substituted phenyl)-acetamide (2a-q, 5 mmol) and ethanol (10 mL). The mixture was stirred for 4-5 h at room temperature (the end of reaction was monitored by TLC), after completion, the mixture was poured into water. The resulting precipitate was collected by filtration, washed well with water and further puried by recrystallization from ethanol to afford target compounds.
  • 16
  • [ 37469-24-2 ]
  • [ 37394-93-7 ]
  • 2-((5,6-diphenyl-1,2,4-triazin-3-yl)thio)-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.3% With triethylamine; In methanol; at 20℃; for 2h; General procedure: A mixture of 2 (265mg, 1.0mmol), different 2-chloro-N-arylacetamide 4a-4q (1.0 mmol) and Et3N (1mL) in methanol (50 mL) was stirred at room temperature for 2 h. After thecompletion of the reaction, the solvent was removed under reduced pressure andthe residue was purified by silica gel column chromatography (EtOAc/petroleumether) to give the title compounds 5a-5q, respectively.
  • 17
  • 4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine [ No CAS ]
  • [ 37394-93-7 ]
  • N-(2-methylphenyl)-2-[4-(6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-d]pyrimidin-4-yl)piperazin-1-yl] acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydrogencarbonate; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 36h; General procedure: The target compounds 9a-f and 14a-f were prepared by nucleophilic substitution of chloro of 2-chloro-N-substitutedphenyl acetamide derivatives 1a-h with 4-(1-piperazinyl) thieno[2,3-d]pyrimidine derivatives 8a,b. Briefly, sodium bicarbonate (2.36mmol, 0.2g) and sodium iodide (2.36mmol, 0.51g) were added to a solution of intermediates 8a,b (2.36mmol) and intermediates 1a-h (2.36mmol) in DMF (30mL). The reaction mixture was stirred for 36h at room temperature, then added to water (50mL) affording a precipitate which was filtered under vacuum and left to dry. The resulting solid was recrystallized from absolute ethanol to give the titled compounds. 5.1.1.1 N-(2-Methylphenyl)-2-[4-(6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl] acetamide 9a (0026) Yellowish white crystals, 87% yield; m.p. 192-193 C; FT-IR (KBr, cm-1): upsilon 3416 (NH), 3020 (CH aromatic), 2922 (CH aliphatic), 1688 (-NH-C=O), 1586 (C=C), 1541 (C=N); 1H NMR (400MHz, CDCl3) delta 9.34 (s, 1H, NH D2O exchangeable), 8.51 (s, 1H, pyrimidine H), 8.08 (d, J=7.8Hz, 1H, ArH), 7.15-7.25 (m, 2H, ArH), 7.06 (d, J=8.2Hz, 1H, ArH), 3.70 (m, 4H, piperazine), 3.39 (s, 2H, -CH2CO-), 3.04 (m, 4H, -CH2-CH2-CH2-), 2.95 (m, 4H, piperazine), 2.48 (m, 2H, -CH2-CH2-CH2-), 2.32 (s, 3H, ArCH3); MS: (Mwt.: 407.5): m/z, 407.3 [M+, (10.88%)], 269 (100%); Anal. Calcd for C22H25N5OS: C, 64.84; H, 6.18; N, 17.18; Found: C, 64.78; H, 6.14; N, 17.1.
  • 18
  • [ 480-40-0 ]
  • [ 37394-93-7 ]
  • 5-hydroxy-2-phenyl-7-(o-tolylamino)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 61h; Chrysin (1) (50 mg, 0.20 mmol), <strong>[37394-93-7]2-chloro-N-(o-tolyl)acetamide</strong> (3) (38 mg, 0.21 mmol) andanhydrous potassium carbonate (56 mg, 0.41 mmol) were dissolved in DMF (2 mL). The reactionmixture was stirred at 80 C for 61 h, then, it was evaporated under reduced pressure. Water (30 mL)was added to the residue and it was extracted with DCM (30 mL). Then, saturated NaCl solution (20mL) was added to the aqueous phase and it was extracted with DCM (2 x 20 mL). The combinedorganic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified withpreparative TLC (DCM : MeOH = 40 : 1) to give 31 mg (46 %) of compound 13 as a yellow solid. M.p.:220-221 C. TLC (DCM : MeOH = 40 : 1); Rf = 0.69.
  • 19
  • [ 480-40-0 ]
  • [ 37394-93-7 ]
  • 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 28h; Chrysin (1) (100 mg, 0.39 mmol), <strong>[37394-93-7]2-chloro-N-(o-tolyl)acetamide</strong> (3) (76 mg, 0.41 mmol) andanhydrous potassium carbonate (56 mg, 0.41 mmol) were dissolved in DMF (4 mL). The reactionmixture was stirred at room temperature for 28 h, then, it was poured into water (30 mL). Afterfiltering off the precipitate, the filtrate was extracted with DCM (3 x 30 mL). The combined organiclayer was dried over MgSO4 and concentrated in vacuo. The filtered precipitation and the crudeproduct obtained by extraction were purified separately with preparative TLC (DCM : MeOH = 40 :1). Combining the pure products 155 mg (98 %) of compound 8 was isolated as a white solid. M.p.:236-237 C. TLC (DCM : MeOH = 40 : 1); Rf = 0.51.
  • 20
  • C9H9N3O3S2 [ No CAS ]
  • [ 37394-93-7 ]
  • 2-((5-(2-(methylsulfonamido)phenyl)-1,3,4-oxadiazol-2-yl)thio)-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide; In ethanol; at 20℃; General procedure: To an ethanolic solution (10 mL) of substituted oxadiazole (4)(1 mmol, 0.27 g) was added KOH (1 mmol, 0.05 g). The reactionmixture was stirred until KOH was dissolved followed by the addition ofacylated aniline (5a) (1 mmol, 0.17 g) at room temperature. Aftercompletion of the reaction (monitored by TLC), the precipitates formedwere filtered off, washed with dilute HCl and then with distilled waterand dried.The similar procedure was followed to prepare other derivatives6(b-l).
  • 21
  • 4-(6,8-diiodo-2-mercapto-4-oxoquinazolin-3-(4H)-yl)benzenesulfonamide [ No CAS ]
  • [ 37394-93-7 ]
  • 2-((6,8-diiodo-4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-yl)thio)-N-o-tolylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate; In acetone; at 20℃; for 18h; General procedure: 4.1.2.1. General procedure. A mixture of 4 (5.85 g, 0.01 mol) and 2-chloro-N-substituted acetamide derivatives (0.01 mol) in dry acetone (30 mL) and anhydrous K2CO3 (1.38 g, 0.01 mol)was stirredat room temperature for 18 h, filtered and the solid product formedwas crystallized from dioxane to give 5e18.4.1.2.2. 2-((6,8-Diiodo-4-oxo-3-(4-sul famoylphenyl)-3,4-dihydroquinazolin-2-yl)thio)-N-phenylacetamide (5)
  • 22
  • 4-(6-iodo-2-mercapto-4-oxoquinazolin-3(4H)-yl)benzenesulfonamide [ No CAS ]
  • [ 37394-93-7 ]
  • 2-((6-iodo-4-oxo-3-(4-sulfamoyl phenyl)-3,4-dihydroquinazolin-2-yl)thio)-N-(o-tolyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In acetone; at 20℃; for 8h; General procedure: General procedure.A mixture of 4 (4.59 g, 0.01 mol) and 2-chloro-N-substitutedacetamide derivatives (0.01 mol) in dry acetone (30 mL) andanhydrous K2CO3 (1.38 g, 0.01 mol) was stirred at room temperaturefor 8 h, filtered and the solid product formed was crystallizedfrom ethanol to give 5-18.
  • 23
  • [ 37394-93-7 ]
  • [ 77395-10-9 ]
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