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[ CAS No. 18364-71-1 ] {[proInfo.proName]}

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Chemical Structure| 18364-71-1
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Product Details of [ 18364-71-1 ]

CAS No. :18364-71-1 MDL No. :MFCD04107483
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ABFSTRGQQNSRNH-UHFFFAOYSA-N
M.W : 179.22 Pubchem ID :826319
Synonyms :

Calculated chemistry of [ 18364-71-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.88
TPSA : 40.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : -0.63
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.7
Solubility : 35.9 mg/ml ; 0.201 mol/l
Class : Very soluble
Log S (Ali) : 0.25
Solubility : 320.0 mg/ml ; 1.78 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.93 mg/ml ; 0.00519 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 18364-71-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338+P310 UN#:1759
Hazard Statements:H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18364-71-1 ]

* 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 [ 18364-71-1 ]

[ 18364-71-1 ] Synthesis Path-Downstream   1~58

  • 1
  • [ 1642-81-5 ]
  • [ 18364-71-1 ]
  • furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
  • α-dimethylamino-bibenzyl-4,4'-dicarboxylic acid [ No CAS ]
  • 2
  • [ 1642-81-5 ]
  • [ 18364-71-1 ]
  • α-dimethylamino-bibenzyl-4,4'-dicarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide man neutralisiert mit Salzsaeure und saeuert mit Essigsaeure an;
  • 3
  • [ 515131-55-2 ]
  • [ 18364-71-1 ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide
  • 4
  • [ 2759-28-6 ]
  • [ 18364-71-1 ]
  • 1-benzyl-4-(4-(dimethylaminomethyl)benzoyl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole 1.) DMF, 70 deg C, 3 h, 2.) RT, 4 d; Multistep reaction;
YieldReaction ConditionsOperation in experiment
Rk. mit Me./HCl -> Methyl-p-(N,N-dimethylaminomethyl)-benzoat;
YieldReaction ConditionsOperation in experiment
α-Chlor-p-toluylsaeure,Dimethylamin/NaI;
4-Aminomethyl-benzoesaeure, Leuckart-Wallach-Rk.;
  • 7
  • [ 18364-71-1 ]
  • [ 99-94-5 ]
  • [ 124-40-3 ]
  • 8
  • [ 18364-71-1 ]
  • [ 121811-18-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 80℃;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 3h; 1 To a solution of 4-((dimethylamino)methyl)benzoic acid (8 equivalents) in dichloromethane was added oxalyl dichloride (7.5 equivalents) and a drop of catalytic N,N- dimethylformamide. After 3 hours, the resulting acid chloride was slowly added to Compound 8 (1 equivalent) in dichloromethane and pyridine (2:1 ratio) until starting material was consumed as verified by LC/MS. The solution was diluted with saturated aqueous ammonium chloride solution and dichloromethane. The layers were separated and the aqueous layer was neutralized with saturated aqueous sodium bicarbonate solution. After extracting with dichloromethane, the organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. The residue was brought up in dichloromethane and diethyl ether (1:2.5 ratio) and the resulting solid was filtered and washed with diethyl ether to give Compound 102 (2.6 mg, 16% yield) as a white solid. H-NMR (400 MHz, MeOD) δ 8.79 (m, 1H), 8.32 (s, 1H), 8.01 (d, 2H), 7.51 (d, 2H), 7.47 (s, 1H), 7.17 (q, 1H), 7.06-7.01 (m, 1H), 6.91 (m, 1H), 6.71-6.68 (m, 1H), 6.01 (s, 2H), 3.61 (s, 2H), 2.30 (s, 6H).
With thionyl chloride In N,N-dimethyl-formamide for 2h; Reflux; General procedures for the synthesis of compounds 7a-7f General procedure: The mixture containing compound 6 (2.51 mmol), methanol (5.0 mL), 2 M NaOH (1.6 mL) was stirred at room temperature for 4 h, concentrated under reduced pressure and acidified with concentrated hydrochloric acid to pH 2. The aqueous phase was concentrated to dryness under reduced pressure to afford the crude 4-aminomethylbenzoic acid (containing sodium chloride) which was carried on the next step without further purification. The 4-aminomethylbenzoic acid (2.51 mmol) and 2 drops of DMF were added to thionyl chloride (10 mL). The mixture was refluxed for2 h. The volatile was removed under reduced pressure to give a pale yellow solid which was then dissolved in anhydrous THF (10 mL) and was added dropwise to a suspension of sodium azide (0.24 g, 3.77 mmol) in 10 mL of THF/H2O (4:1, v/v) at 0-5°C. Then the mixture was stirred at room temperature overnight and THF was removed under reduced pressure. The aqueous phase was extracted with dichloromethane (20 mL 3). The organic layerwas combined, washed with brine (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to produce compounds 7a-7f as yellow or brown oil.
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Method b) General procedure: Carboxylic acid (1 eq) was suspended in DCM (0.15 mmol / mL) followed by dropwise addition of oxalyl chloride (2 eq) and 3 drops of DMF. The reaction was stirred at room temperature for 2 h, followed by addition of 1 more eq of oxalyl chloride. The mixture was concentrated in vacuo and azeotroped with toluene to afford the crude product.

  • 9
  • [ 18364-71-1 ]
  • [ 64769-68-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: SOCl2; DMF / 1,2-dichloro-ethane / 80 °C 2.1: i-Pr2NEt / 1,2-dichloro-ethane / 0 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / -70 °C 3.2: tetrahydrofuran; hexane / -70 - 20 °C 4.1: HCl / tetrahydrofuran / 20 °C
  • 10
  • [ 18364-71-1 ]
  • [ 945761-31-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / 1,2-dichloro-ethane / 80 °C 2: i-Pr2NEt / 1,2-dichloro-ethane / 0 - 20 °C
  • 11
  • [ 18364-71-1 ]
  • 5-[2-(4-dimethylaminomethyl-phenyl)-2-oxo-ethyl]-3-phenyl-isoxazole-4-carboxylic acid methylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: SOCl2; DMF / 1,2-dichloro-ethane / 80 °C 2.1: i-Pr2NEt / 1,2-dichloro-ethane / 0 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 1 h / -70 °C 3.2: tetrahydrofuran; hexane / -70 - 20 °C
  • 12
  • [ 84545-14-2 ]
  • [ 18364-71-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water 2: diluted aq. barium hydroxide solution
  • 13
  • [ 18153-53-2 ]
  • [ 18364-71-1 ]
YieldReaction ConditionsOperation in experiment
100% 108.b b) b) 4-(N,N-dimethylaminomethyl)benzoic Acid Following the procedure of Example 1(g), except substituting methyl 4-(N,N-dimethylaminomethyl)benzoate for N-(4-pyridinylmethoxycarbonyl)-L-leucine methyl ester, the title compound was prepared as a white solid (1.6 g, 100%). 1H NMR (400 MHz, CD3OD) d 7.94 (d, 2H), 7.36 (d, 2H), 3.64 (s, 2H), 2.35 (s, 6H).
Stage #1: methyl 4-(N,N-dimethylaminomethyl)benzoate With sodium hydroxide In methanol at 20℃; for 4h; Stage #2: With hydrogenchloride In methanol; water 4.1.14. General procedures for the synthesis of compounds 7a-7f General procedure: The mixture containing compound 6 (2.51 mmol), methanol (5.0 mL), 2 M NaOH (1.6 mL) was stirred at room temperature for 4 h, concentrated under reduced pressure and acidified with concentrated hydrochloric acid to pH 2. The aqueous phase was concentrated to dryness under reduced pressure to afford the crude 4-aminomethylbenzoic acid (containing sodium chloride) which was carried on the next step without further purification. The 4-aminomethylbenzoic acid (2.51 mmol) and 2 drops of DMF were added to thionyl chloride (10 mL). The mixture was refluxed for2 h. The volatile was removed under reduced pressure to give a pale yellow solid which was then dissolved in anhydrous THF (10 mL) and was added dropwise to a suspension of sodium azide (0.24 g, 3.77 mmol) in 10 mL of THF/H2O (4:1, v/v) at 0-5°C. Then the mixture was stirred at room temperature overnight and THF was removed under reduced pressure. The aqueous phase was extracted with dichloromethane (20 mL 3). The organic layerwas combined, washed with brine (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to produce compounds 7a-7f as yellow or brown oil.
  • 14
  • [ 118293-17-7 ]
  • [ 18364-71-1 ]
  • [ 118308-77-3 ]
YieldReaction ConditionsOperation in experiment
56 mg (40%) With triethylamine In dichloromethane 2 Preparation of p-N,N-Dimethylaminomethylbenzoic acid, [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole-1-yl] methyl ester (Method B) EXAMPLE 2 Preparation of p-N,N-Dimethylaminomethylbenzoic acid, [2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole-1-yl] methyl ester (Method B) p-N,N-Dimethylaminomethylbenzoic acid (50 mg, 0.28 mmoles) and triethyl amine (60 mg, 0.6 mmoles) were dissolved in methylene chloride (10 ml). A solution of 1-chloromethyl-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl) methyl]sulfinyl]-1H-benzimidazole (100 mg, 0,27 mmoles) in methylene chloride (5 ml) was added. After 10 hr at room temperature the methylene chloride solution was washed with 0,5M sodium hydroxide (5 ml) and brine (5 ml). The organic phase was dried over sodium sulphate, filtered and evaporated at a reduced pressure. The residue is the essentially pure title compound. Yield: 56 mg (40%).
  • 15
  • [ 1035270-66-6 ]
  • [ 18364-71-1 ]
  • [ 1035269-31-8 ]
YieldReaction ConditionsOperation in experiment
25% Stage #1: 4-((dimethylamino)methyl)benzoic acid With oxalyl dichloride In dichloromethane at 20℃; for 1.5h; Stage #2: tert-butyl 5-amino-3-(3,5-dimethoxyphenethyl)-1H-pyrazole-1-carboxylate With pyridine In dichloromethane at 20℃; for 2h; Stage #3: With trifluoroacetic acid In dichloromethane at 20℃; for 18h; 47 Oxalyl chloride (61 μl, 0.69 mmol, 1.1 eq) was added dropwise to 4-(dimethylaminomethyl)benzoic acid (113 mg, 0.63 mmol, 1 eq) in DCM (2.5 ml) containing 1 drop of DMF. After stirring at ambient temperature for 1.5 h, a solution of tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate (196 mg, 0.56 mmol, 0.9 eq) and pyridine (137 μL, 1.69 mmol, 2.70 eq) in DCM (2 ml) was added to the reaction mixture and stirring was continued at ambient temperature for a further 2 h. A solution of TFA (384 μL, 5.16 mmol, 8.25 eq) in DCM (3.5 ml) was then added and stirring was continued at ambient temperature for 18 h. The reaction mixture was concentrated and the crude product was purified by reverse-phase prep. HPLC (basic) using a gradient of acetonitrile in water containing 1% ammonium hydroxide solution. The clean fractions were taken and evaporated to afford the title compound as a colourless solid (65 mg, 25% yield).; 1H NMR (399.902 MHz, DMSO) δ 2.09 (6H, s), 2.81 (4H, s), 3.38 (2H, s), 3.65 (6H, s), 6.26-6.25 (1H, m), 6.35 (2H, d), 6.40 (1H, s), 7.31 (2H, d), 7.87 (2H, d), 10.51 (1H, br.s), 12.07 (1H, br.s). MS: m/z 409 (MH+) Mean of n=1, FGFR Kinase assay-Caliper, IC50 0.019 μM.
  • 16
  • [ 938121-64-3 ]
  • [ 18364-71-1 ]
  • [ 1253734-83-6 ]
YieldReaction ConditionsOperation in experiment
26% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;
  • 17
  • [ 1264943-21-6 ]
  • [ 18364-71-1 ]
  • [ 1264941-44-7 ]
YieldReaction ConditionsOperation in experiment
15% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; 58 Example 58: Preparation of Compound No. 1.601; To a mixture of l-methyl-2-(piperidin-4-yloxy)-lH-[4,4']bipyrimidinyl-6-one (290 mg, 1.0 mmol), 4-dimethylaminomethyl benzoic acid (180 mg, 1.0 mmol),N-(3-dimethylaminopropyl)-N'-ethylcarbodmide hydrochloride (380 mg, 2.0 mmol) and 1-hydroxybenzotriazole monohydrate (310 mg, 2.0 mmol) in N,N-dimethylformamide (10 ml) was added N,N-diisopropylethylamine (130 mg, 1.0 mmoO at room temperature. The mixture was stirred at room temperature for 3 hours. The mixture was partitioned between water and dichlorome thane. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate = 15/85) to afford 2-[l-(4-dimethylaminomethyl-benzoyl)piperidin-4-yloxy]-l-methyl- lH-[4,4']bipyrimidinyl-6-one as a colorless solid (66 mg, 0.15 mmol, 15%).
  • 18
  • [ 18364-71-1 ]
  • [ 1446359-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h 2: pyridine / dichloromethane
  • 19
  • [ 18364-71-1 ]
  • [ 81644-19-1 ]
  • [ 1583315-20-1 ]
YieldReaction ConditionsOperation in experiment
60% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 144h;
  • 20
  • [ 67-56-1 ]
  • [ 18364-71-1 ]
  • [ 18153-53-2 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride at 70℃;
  • 22
  • [ 18364-71-1 ]
  • C20H24N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: thionyl chloride / 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 3: thionyl chloride / toluene / 1 h / 20 °C 4: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 - 20 °C 5: hydroxylamine / methanol; dichloromethane / 0 - 20 °C
  • 23
  • [ 18364-71-1 ]
  • C22H27N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 3: thionyl chloride / toluene / 1 h / 20 °C 4: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 - 20 °C
  • 24
  • [ 18364-71-1 ]
  • C10H14ClN*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 3: thionyl chloride / toluene / 1 h / 20 °C
  • 25
  • [ 18364-71-1 ]
  • [ 13990-98-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C
  • 26
  • [ 18364-71-1 ]
  • [ 309718-03-4 ]
  • N-[3-[(1H-benz[d]imidazol-2-yl)amino]propyl]-4-[(dimethylamino)methyl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 1.5h;
  • 27
  • [ 18364-71-1 ]
  • C10H17NO4*C2HF3O2 [ No CAS ]
  • C15H20N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 16h; Synthesis of fragments General procedure: The fragment carboxylic acid (0.35 mmol) was dissolved in dimethylformamide (0.2 M, 1.75 mL), then 14 (42.6 mg, 0.35 mmol), HBTU (128 mg, 0.34 mmol), and HOBT (51.8 mg, 0.38 mmol) were added, followed by diisopropylethylamine (175 µL, 1.047 mmol). The reaction was stirred at 23 °C for 16 h. TLC at 16 h showed conversion to product. The reaction was quenched with H2O (5 mL) and extracted with DCM (3 x 5 mL). The combined organic layers were washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL), and saturated aqueous NaCl (10 mL). The organic layer was dried over MgSO4, filtered, and evaporated. Purification with flash column chromatography with CH3OH/CH2Cl2 ( CH3OH gradient 0 → 5 %).
  • 28
  • [ 1571-08-0 ]
  • [ 18364-71-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / dichloromethane / 5 h / 20 °C 2.1: sodium hydroxide / methanol / 4 h / 20 °C 2.2: pH 2
  • 29
  • [ 18364-71-1 ]
  • 1-(4-((dimethylamino)methyl)phenyl)-3-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-6-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide / 2 h / Reflux 2: sodium azide / tetrahydrofuran; water / 0 - 20 °C 3: toluene / 2 h / Reflux
  • 30
  • [ 18364-71-1 ]
  • 4-((dimethylamino)methyl)benzoyl azide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 2 h / Reflux 2: sodium azide / tetrahydrofuran; water / 0 - 20 °C
  • 31
  • [ 18364-71-1 ]
  • C16H16N4O2 [ No CAS ]
  • C26H27N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 80℃; for 18h;
  • 32
  • [ 18364-71-1 ]
  • 3-(6-(3-(pyrrolidin-1-yl)propoxy)benzo[d]oxazole-2-yl)aniline [ No CAS ]
  • 4-((dimethylamino)methyl)-N-(3-(6-(3-(pyrrolidin-1-yl)propoxy)benzo[d]oxazol-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4-((dimethylamino)methyl)benzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.25h; Stage #2: 3-(6-(3-(pyrrolidin-1-yl)propoxy)benzo[d]oxazole-2-yl)aniline In N,N-dimethyl-formamide at 20℃; for 12h; 4.1.21 procedure for the synthesis of 44, 45, 46 and 47 General procedure: The acid (2mmol) and HATU (1.5mmol) were dissolved in dry DMF and DIPEA (4mmol) was added to it. After 15min respective amine (1mmol) was added and the reaction mixture stirred at room temperature for 4-5h. The reaction mixture was extracted with 5% Methanol/CHCl3 system. Column chromatography was done using CHCl3/Methanol system to get the pure product.
  • 33
  • [ 18364-71-1 ]
  • 2-(4-((dimethylamino)methyl)phenyl)-7-(hydroxymethyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one [ No CAS ]
  • 2-(4-((dimethylamino)methyl)benzamido)-6-(hydroxymethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2: triethylamine / acetonitrile / 3 h / 60 °C 3: lithium borohydride / tetrahydrofuran; diethyl ether / 24 h / 40 °C
  • 34
  • [ 18364-71-1 ]
  • C22H29N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2: triethylamine / acetonitrile / 3 h / 60 °C
  • 35
  • [ 18364-71-1 ]
  • 2-amino-7-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(isoquinolin-6-yl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]
  • 2-(4-((dimethylamino)methyl)benzamido)-7-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(isoquinolin-6-yl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]
  • 2-(4-((dimethylamino)methyl)benzamido)-7-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(isoquinolin-6-yl)-5-methyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
115 mg With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 2h; 137A; 137B 7-(3-Fluoro-4-(trifluoromethyl)phenyl)-N-(isoquinolin-6-yl)-5-methyl-2-(3-(piperidin-1-yl)propanamido)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxamide (Example 131) General procedure: A mixture of Example 130 (0.26 g, 0.54 mmol), 3-piperidin-1-yl propionic acid (89 mg, 0.57 mmol) and DIPEA (0.19 mL, 1.08 mmol) in DCM (20 ml) at RT was treated with HATU (225 mg, 0.59 mmol) and stirred for 2 h. The reaction mixture was concentrated in vacuo and the residue partitioned between water and 2-methyl THF. The organic extracts were separated, combined, washed with water and saturated brine, dried (Na2SO4) and evaporated. The crude product was purified by MDAP (basic) to give the title compound as a white solid (115 mg).
  • 36
  • [ 14568-13-9 ]
  • [ 18364-71-1 ]
  • C12H18ClNO3PtS [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sodium acetate In ethanol at 65℃; for 5h; Inert atmosphere;
  • 37
  • [ 18364-71-1 ]
  • 2-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-5-amine [ No CAS ]
  • 4-((dimethylamino)methyl)-N-(2-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-5-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 16h;
  • 38
  • [ 619-66-9 ]
  • [ 18364-71-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dmap / tetrahydrofuran / 2 h / 80 °C 2.1: acetic acid / methanol / 0.17 h / 20 °C 2.2: 18 h / 60 °C 3.1: hydrogenchloride / 1,4-dioxane / 16 h / Reflux
  • 39
  • [ 65874-27-3 ]
  • [ 18364-71-1 ]
  • 40
  • [ 1004759-91-4 ]
  • [ 18364-71-1 ]
YieldReaction ConditionsOperation in experiment
50.6% With hydrogenchloride In 1,4-dioxane for 16h; Reflux; 3 Step 3 To a suspension of HCl (7.23 mL, 14.5 mmol) in 1,4-dioxane (5 mL) was added tert-butyl 4-((dimethylamino)methyl)benzoate (LXXXVIII) (0.92 g, 3.91 mmol). The reaction was heated under reflux for 16 h. The reaction was then cooled and the solid was collected by filtration, washed with dioxane and dried under vacuum to produce 4-((dimethylamino)methyl)benzoic acid (LXXXIX) as a white solid (427 mg, 1.98 mmol, 50.6% yield). ESIMS found for C10H13NO2 m/z 180. (M+H).
  • 41
  • [ 18364-71-1 ]
  • 6-(4-cyclopentylpiperazin-1-yl)-9-(3-(4-ethylpiperazin-1-yl)propyl)-9H-purin-2-amine [ No CAS ]
  • N-(6-(4-Cyclopentylpiperazin-1-yl)-9-(3-(4-ethylpiperazin-1-yl)propyl)-9H-purin-2-yl)-4-((dimethylamino)-methyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With pyridine; trichlorophosphate at 0℃; for 2h; 9 Synthesis of N-(6-(4-cyclopentylpiperazin-l-yl)-9-(3-(4-ethylpiperazin-l-yl)propyl)-9H-purin-2- yl)-4-((dimethylamino)methyl)benzamide (27): A solution of compound 23 (0.10 g, 0.23 mmol) and 4-((dimethylamino)methyl)benzoic acid (0.048 g, 0.27 mmol) in pyridine was added POCI3 (0.03 mL, 0.35 mmol) at 0 °C and stirred for 2hours. The reaction mixture was poured into crushed ice and neutralised with saturated Na2C03 solution. The aqueous layer was extracted with chloroform, dried over Na2S04 and evaporated under vacuum. The residue was purified by silica gel column chromatography to give compound 27 (yield 53%). 1H NMR (300MHz, CDCI3) δ ppm 8.30 (s, -NH), 7.87 (d, J = 7.8 Hz, 2H), 7.67 (s, 1H), 7.43 (d, J = 7.5 Hz, 2H), 4.22 (t, J = 6.9 Hz, 1H), 3.50 (s, 2H), 2.64 (m, 8H), 2.55 (m, 8H), 2.37 (t, J = 6.6 Hz, 2H), 2.27 (s, 6H), 2.06 (t, J = 6.6 Hz, 2H), 1.9 (m, 2H), 1.72 (m, 2H), 1.59-1.44 (m, 4H), 1.25 (m, 4H), 1.15 (t, J = 7.5 Hz, 3H). ESI-MS m/z 603.26(M+H).
53% With trichlorophosphate In pyridine at 0℃; for 2h;
  • 42
  • [ 18364-71-1 ]
  • 6-(4-ethylpiperazin-1-yl)-9-(3-(4-ethylpiperazin-1-yl)propyl)-9H-purin-2-amine [ No CAS ]
  • 4-((dimethylamino)methyl)-N-(6-(4-ethylpiperazin-1-yl)-9-(3-(4-ethylpiperazin-1-yl)propyl)-9H-purin-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With pyridine; trichlorophosphate In dichloromethane 7 Synthesis of 4-((dimethylamino)methyl)-N-(6-(4-ethylpiperazin-l-yl)-9-(3-(4-ethylpiperazin-l- yl)propyl)-9H-purin-2-yl)benzamide (16): Reaction of Compound 4 (0.2 g, 0.5 mmol) and 4- ((dimethylamino)methyl)benzoic acid (0.13 g, 0.6 mmol) was done according to procedure B. Then column chromatography was done by using CHCI3/MeOH system to get the pure product 16 (yield 53%).1H NMR (300MHz, DMSO-d6) δ ppm 8.06 (s, -NH), 7.86 (d, J = 8.4 Hz, 2H), 7.70 (s, 1H), (0146) 7.40 (d, J = 7.8 Hz, 2H), 4.12 (m, 6H), 3.97 (t, J = 6.0 Hz, 2H), 3.16-3.09 (m, 2H), 2.72 (s, 6H), 2.47- (0147) 2.41 (m, 8H), 2.40-2.37 (m, 4H), 2.27-2.25 (m, 4H), 1.96-1.84 (m, 2H), 1.03 (t, J = 6.3 Hz, 6H). ESI- MS m/z 563.32 (M+H).
  • 43
  • [ 18364-71-1 ]
  • 4′-(methoxymethoxy)-4-nitro-[1,1′-biphenyl]-3-amine [ No CAS ]
  • C24H25N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; N,N-dimethyl-formamide 4'-(methoxymethoxy)-4-nitro-[1,1'-biphenyl]-3-amine and p-phenylcarboxylic acid with R group, with coupling reagents such as HOBt, DMAP, EDCINucleophilic substitution reaction between DCM and DMF solution,Forming an R groupN -(4'-(methoxymethoxy)-4-nitro-[1,1'-biphenyl]-3-yl)benzamide.The R group here is -CH2 N(CH3)2 ,-N(CH3)2, -CH2 CH(CH3)2, -CH(CH3)2,Substituents such as -CH2 CH2 CH3.
  • 44
  • [ 18364-71-1 ]
  • C24H27N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; dichloromethane 2: iron; acetic acid; water / ethanol / Heating
  • 45
  • [ 18364-71-1 ]
  • C22H23N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; dichloromethane 2: iron; acetic acid; water / ethanol / Heating 3: trimethylsilyl bromide / dichloromethane / 20 °C
  • 46
  • [ 18364-71-1 ]
  • C23H22F3N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; dichloromethane 2: iron; acetic acid; water / ethanol / Heating 3: trimethylsilyl bromide / dichloromethane / 20 °C 4: pyridine
  • 47
  • [ 18364-71-1 ]
  • N-(4-amino-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-4-((dimethylamino)methyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide; dichloromethane 2: iron; acetic acid; water / ethanol / Heating 3: trimethylsilyl bromide / dichloromethane / 20 °C 4: pyridine 5: tris-(dibenzylideneacetone)dipalladium(0); XPhos; potassium acetate / 1,4-dioxane / 90 °C
  • 48
  • [ 21169-65-3 ]
  • [ 18364-71-1 ]
  • 4-[(dimethylamino)methyl]-N-(5-methyl-3-phenylisoxazol-4-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; Inert atmosphere;
  • 49
  • [ 18364-71-1 ]
  • N-(3-(2-(5-amino-1-(tert-butyl)-1H-pyrazol-3-yl)ethyl)phenyl)-4-((dimethylamino)methyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 45 °C 2: pyridine / dichloromethane / 20 °C
  • 50
  • [ 18364-71-1 ]
  • N-(1-(tert-butyl)-3-(3-(4-((dimethylamino)methyl)benzamido)phenethyl)-1H-pyrazol-5-yl)-4-morpholinobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 45 °C 2: pyridine / dichloromethane / 20 °C 3: pyridine / dichloromethane
  • 51
  • [ 18364-71-1 ]
  • 4-((dimethylamino)methyl)-N-(3-(2-(5-(4-morpholinobenzamido)-1H-pyrazol-3-yl)ethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 45 °C 2: pyridine / dichloromethane / 20 °C 3: pyridine / dichloromethane 4: formic acid / 1 h / 100 °C
  • 52
  • [ 18364-71-1 ]
  • 4-((dimethylamino)methyl)benzoyl chloride hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 45℃; 32 4-((dimethylamino)methyl)benzoyl chloride To 4-((dimethylamino)methyl)benzoic acid (0.730 g, 4.07 mmol) in dry DCM (30 ml) was added oxalyl dichloride (3.45 ml, 40.7 mmol) followed by N,N-dimethylformamide (0.016 ml, 0.204 mmol). The resulting mixture was stirred overnight at 45°C and then evaporated. A small sample was treated with MeOH and analysed by mass.ESI + m/z 194 [M+H] (methyl ester).
  • 53
  • [ 18364-71-1 ]
  • 1-ethoxycarbonyl-4-(4'-dimethylaminomethylphenyl)semicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 90 - 100 °C / Inert atmosphere 2: toluene / 1 h / 40 - 46 °C
  • 54
  • [ 18364-71-1 ]
  • 4-(4'-dimethylaminomethylphenyl)-1,2,4-triazolidine-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 90 - 100 °C / Inert atmosphere 2: toluene / 1 h / 40 - 46 °C 3: potassium carbonate / water / 2 h / 95 °C
  • 55
  • [ 18364-71-1 ]
  • 6-(4-ethylpiperazin-1-yl)-9-(3-(pyrrolidin-1-yl)-propyl)-9H-purin-2-amine [ No CAS ]
  • 4-((dimethylamino)methyl)-N-(6-(4-ethylpiperazin-1-yl)-9-(3-(pyrrolidin-1-yl)propyl)-9H-purin-2-yl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With trichlorophosphate In pyridine at 0℃; for 2h;
  • 56
  • [ 18364-71-1 ]
  • 6-(4-cyclopentylpiperazin-1-yl)-9-(3-(pyrrolidin-1-yl)propyl)-9H-purin-2-amine [ No CAS ]
  • N-(6-(4-cyclopentylpiperazin-1-yl)-9-(3-(pyrrolidin-1-yl)propyl)-9H-purin-2-yl)-4-((dimethylamino)methyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With trichlorophosphate In pyridine at 0℃; for 2h;
  • 57
  • [ 18364-71-1 ]
  • C10H12N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; triethylamine In toluene at 90 - 100℃; for 1h; Inert atmosphere; 5 Example 5 Synthesis of 1-Ethoxycarbonyl-4-(4'-Dimethylaminomethylphenyl)Semicarbazide [0099] To a 2-L four-necked glass flask, a mechanical stirrer, a thermometer, a Dimroth condenser and a gas inlet tube were attached. Into the flask, 109.32 g (0.61 mol) of No.3 4-dimethylaminomethylbenzoic acid, and 1,000 mL of dehydrated No. toluene were charged, and the mixture was stirred under a nitrogen flow, to form a white slurry. [0100] When 73.51 g (0.73 mol) of triethylamine, and 199.92 g (0.73 mol) of diphenylphosphoryl azide were added to the white slurry, the temperature inside the system increased to 30°C., and a light yellow transparent solution was formed. The flask was heated by placing the flask in an oil bath (100°C.), and the reaction was caused for 1 hour with the temperature inside the system being 90 to 100°C. Evolution of nitrogen gas was observed at a temperature inside the system of about 70°C. or higher, and a dark orange solution was formed.
  • 58
  • [ 18364-71-1 ]
  • N-5-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-[1,2,4]triazolo[4,3-c]-pyrimidine-5,8-diamine [ No CAS ]
  • 4-((dimethylamino)methyl)-N-(5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 16h;
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