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[ CAS No. 3914-42-9 ] {[proInfo.proName]}

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Chemical Structure| 3914-42-9
Chemical Structure| 3914-42-9
Structure of 3914-42-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3914-42-9 ]

CAS No. :3914-42-9 MDL No. :MFCD06655111
Formula : C4H5ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :KJLQSWULHSLSOM-UHFFFAOYSA-N
M.W : 132.55 Pubchem ID :3826620
Synonyms :

Calculated chemistry of [ 3914-42-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.03
TPSA : 38.92 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) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : 0.96
Log Po/w (MLOGP) : 0.28
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.42
Solubility : 5.0 mg/ml ; 0.0377 mol/l
Class : Very soluble
Log S (Ali) : -0.97
Solubility : 14.2 mg/ml ; 0.107 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.24
Solubility : 0.764 mg/ml ; 0.00577 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 3914-42-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3265
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3914-42-9 ]

* 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 [ 3914-42-9 ]

[ 3914-42-9 ] Synthesis Path-Downstream   1~30

  • 2
  • [ 3914-42-9 ]
  • [ 3454-66-8 ]
  • [ 31875-40-8 ]
  • 3
  • [ 1066-97-3 ]
  • [ 3914-42-9 ]
  • [ 31875-39-5 ]
  • 4
  • [ 5871-16-9 ]
  • [ 3914-42-9 ]
  • [ 37934-12-6 ]
  • 7
  • [ 3914-42-9 ]
  • [ 1000686-15-6 ]
YieldReaction ConditionsOperation in experiment
With sodium azide; In N,N-dimethyl-formamide; at 22℃; for 18h; 2-(Azidomethyl)-5-methyl-1,3,4-oxadiazole. A solution of <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (R. Rufenacht, Helv. Chim. Acta, 55, 1979, 1972) (2.00 g, 15.09 mmol) in N,N-dimethylformamide (75 ml) was treated at 22 C. with sodium azide (3.0 g, 46.1 mmol) and the resulting mixture was stirred for 18 h. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure followed by chromatography of the residue on silica gel (elution toluene-ethyl acetate 0-10%) gave 1.78 g (84% yield) of the title azide as a clear oil. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.60 (3H, s, CH3), 4.55 (2H, s, CH2). MS (ESI+) m/e 140 [M+H+].
  • 8
  • [ 3914-42-9 ]
  • [ 1009368-12-0 ]
YieldReaction ConditionsOperation in experiment
25.7% Compound 36A. tert-Butyl 3-((5-methyl-l,3,4-oxadiazol-2-yl)methoxy)azetidine- 1-carboxylate <n="121"/>[00225] To a solution of l-Boc-3-(hydroxyl)azetidine (250 mg, 1.443 mmol) in THF (3 mL) at 0 0C, was added NaH (75 mg, 1.876 mmol) in portions. The mixture was stirred at 0 0C for 0.5 hour, then at RT for 0.5 hour. To the above mixture was added a solution of 2-(Chloromethyl)-5-methyl-l,3,4-oxadiazole (191 mg, 1.443 mmol) in THF (3 mL) slowly. After stirring at RT overnight, the mixture was quenched with NH4Cl (10 mL, saturated aqueous), then extracted with EtOAc (3 X 30 mL). Combined organic layers were dried (MgSO4), concentrated, and purified via column chromatography (Sitheta2, 0-70% EtOAc in n-hexane) to provide compound 36A as colorless oil (100 mg, 25.7 % yield). LC/MS (m/z) = 270 (M+H)+. 1H NMR (400 MHz, CDCl3) delta ppm 4.60 (s, 2 H), 4.29 - 4.39 (m, 1 H), 4.04 - 4.10 (m, 2 H), 3.81 (dd, J=9.67, 4.39 Hz, 2 H), 2.55 (s, 3 H), 1.38 - 1.42 (s, 9 H).
  • 9
  • [ 831-82-3 ]
  • [ 3914-42-9 ]
  • 5-methyl-2-[(4-phenoxyphenoxy)-methyl]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; EXAMPLE 3 5-Methyl-2-[(4-phenoxyphenoxy)-methyl]-1,3,4-oxadiazole (compound no. 20.24) 9.3 g of 4-phenoxyphenol and 9 g of potassium carbonate are stirred in 75 ml of anhydrous dimethylformamide for 1 hour at 80 C. Subsequently, 6.6 g of <strong>[3914-42-9]2-chloromethyl-5-methyl-1,3,4-oxadiazole</strong> in 20 ml of anhydrous dimethylformamide is dripped in. The mixture is stirred for 10 hours at 80 C. and at room temperature (approx. 20 C.) overnight. The mixture is then stirred into 500 ml of ice water and extracted three times with ethyl acetate. After drying over sodium sulfate and removal of the solvent, the residue is purified by chromatography over silica gel using n-hexane/ethyl acetate (4:1) as eluant. There is obtained 12 g of 5-methyl-2-[(4-phenoxyphenoxy)-methyl]-1,3,4-oxadiazole; colorless crystals; m.p.: 78-79 C.
  • 10
  • [ 2107-78-0 ]
  • [ 3914-42-9 ]
  • 3,4-Dimethyl-7-(2-methyl-1,3,4-oxadiazol-5-yl)-methoxycoumarin [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; NaH; EXAMPLE 1 3,4-Dimethyl-7-(2-methyl-1,3,4-oxadiazol-5-yl)-methoxycoumarin 5.0 g of 7-hydroxy-3,4-dimethylcoumarin in 20 ml of 0.9 g of NaH (80%) in 50 ml of dimethylformamide at room temperature. After 45 minutes, 3.5 g of <strong>[3914-42-9]2-chloromethyl-5-methyl-1,3,4-oxadiazole</strong>, dissolved in 20 ml of dimethylformamide, were added and the mixture was stirred overnight at room temperature. The reaction solution was hydrolyzed with ice water, and the precipitated solid was filtered off under suction and recrystallized from methanol. Yield: 4.28 g (57%), mp. 159 C. C15 H14 N2 O4 (286). Calculated: 62.93 C 4.93 H 9.78 N 22.35 O. Found: 63.0 C 4.9 H 9.7 N 22.2 O.
  • 11
  • [ 156-57-0 ]
  • [ 3914-42-9 ]
  • 2-[(2-methyl-1,3,4-oxadiazol-5-yl)methylthio]ethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; A. 2-[(2-Methyl-1,3,4-oxadiazol-5-yl)methylthio]ethylamine Cysteamine hydrochloride (1.13 g; 0.01 mole) was added to a stirred solution of sodium methylate (1.08 g; 0.02 mole) in 20 ml of methanol at 0 under an argon atomsphere. The mixture was stirred for 1 hour at 0 and the resultant suspension was added dropwise over a period of 25 minutes to a stirred solution of <strong>[3914-42-9]2-methyl-5-chloromethyl-1,3,4-oxadiazole</strong> (1.32 g; 0.01 mole) [prepared by the procedure described in Hel. Chim. Acta, 55, 1979 (1972)] in 15 ml of methanol at 0. The reaction mixture was stirred at ambient temperature for 45 minutes, concentrated to near dryness, and then diluted with methylene chloride, filtered and evaporated under reduced pressure to give the title compound (1.92 g) as a yellow oil. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances delta: 3.87 (s, 2H); 2.8 (m, 4H); 2.53 (s, 3H).
With sodium methylate; In methanol; A. 2-[(2-Methyl-1,3,4-oxadiazol-5-yl)methylthio]ethylamine Cysteamine hydrochloride (1.13 g; 0.01 mole) was added to a stirred solution of sodium methylate (1.08 g; 0.02 mole) in 20 ml of methanol at 0 under an argon atmosphere. The mixture was stirred for 1 hour at 0 and the resultant suspension was added dropwise over a period of 25 minutes to a stirred solution of <strong>[3914-42-9]2-methyl-5-chloromethyl-1,3,4-oxadiazole</strong> (1.32 g; 0.01 mole) [prepared by the procedure described in Hel. Chim. Acta, 55, 1979 (1972)] in 15 ml of methanol at 0. The reaction mixture was stirred at ambient temperature for 45 minutes, concentrated to near dryness, and then diluted with methylene chloride, filtered and evaporated under reduced pressure to give the title compound (1.92 g) as a yellow oil. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances delta: 3.87 (s, 2H); 2.8 (m, 4H); 2.53 (s, 3H).
  • 12
  • [ 452-12-0 ]
  • [ 5292-43-3 ]
  • [ 3914-42-9 ]
  • [ 824983-34-8 ]
  • 13
  • [ 1104382-82-2 ]
  • [ 3914-42-9 ]
  • [ 1235840-74-0 ]
  • 14
  • [ 1260585-11-2 ]
  • [ 3914-42-9 ]
  • [ 1523413-08-2 ]
  • 15
  • [ 75-64-9 ]
  • [ 3914-42-9 ]
  • [ 1249996-28-8 ]
YieldReaction ConditionsOperation in experiment
71% In N,N-dimethyl-formamide; at 20℃; for 16h; a) 2-Methyl-N-((5-methyl- 1 ,3,4-oxadiazol-2-yl)methyl)propan-2-amine A suspension of 2-methylpropan-2-amine (75-64-9, 141 mg, 202 mu, 1.92 mmol) and 2- (chloromethyl)-5-methyl-l,3,4-oxadiazole (3914-42-9, 50 mg, 377 muiotaetaomicron) in DMF (200 mu) was stirred at ambient temperature for 16 h. The mixture was poured onto ice- water (20 mL) and extracted with CH2CI2 (2 x 30 mL). The combined extracts were washed with ice-water (20 mL), dried over Na2S04 and concentrated in vacuo to give a yellow oil. The crude product was purified by preparative TLC (silica gel 1 mm, EtOAc/diethyl amine 95:5, elution with DCM/EtOAc 1: 1) to give the title compound (45 mg, 71%) as yellow oil; MS (EI): m/e = 170.2 [MH+] .
  • 16
  • [ 3914-42-9 ]
  • [ 765-30-0 ]
  • [ 1249340-56-4 ]
YieldReaction ConditionsOperation in experiment
35% at 20℃; for 16h; a) Cyclopropyl-(5-methyl-[l,3,4]oxadiazol-2-ylmethyl)-amine A mixture of cyclopropanamine (765-30-0, 194 mg, 236 mu, 3.39 mmol) and 2- (chloromethyl)-5-methyl-l,3,4-oxadiazole (3914-42-9, 90 mg, 679 muiotaetaomicron) was stirred for 16 h at ambient temperature. The mixture was concentrated under reduced pressure and the residue taken up in ice- water / saturated aqueous Na2C03 solution 1/1 (20 mL) and EtOAc (30 mL). The layers were separated and the aqueous layer was extracted one more time with EtOAc (30 mL). The combined extracts were washed with ice-water / brine 1/1 (15 mL), dried over Na2S04 and brought to dryness to give the title compound (36 mg, 35%) as yellow oil which was sufficiently pure to be used in the next reaction step; MS (EI): m/e = 154.2 [MH+].
  • 17
  • [ 768-94-5 ]
  • [ 3914-42-9 ]
  • [ 1443123-49-6 ]
  • 18
  • 7-(3,3-difluoropyrrolidin-1-yl)-5-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]-3H-triazolo[4,5-d]pyrimidine [ No CAS ]
  • [ 3914-42-9 ]
  • 2-[[7-(3,3-difluoropyrrolidin-1-yl)-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxytriazolo[4,5-d]pyrimidin-3-yl]methyl]-5-methyl-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 5h; General procedure: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 71; 2-[[7-(3,3-Difluoropyrrolidin-l-yl)-5-[(2S)-l,l,l-trifluoropropan-2-yl]oxytriazolo[4,5- d]pyrimidin-3-yl]methyl]-5-methyl-l,3,4-oxadiazole; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin- l-yl)-3-[[2- (trifluoromethyl)phenyl] methyl] triazolo [4, 5 -d] pyrimidin- 5 - amine (example 22) the title compound was prepared from 7-(3,3-difluoropyrrolidin-l-yl)- 5-[(lS)-2,2,2-trifluoro- l-methyl-ethoxy]-3H-triazolo[4,5-d]pyrimidine and 2- (chloromethyl)-5-methyl-l,3,4-oxadiazole. MS(m/e): 435.4 (MH+).
  • 19
  • 6-(4-chlorophenyl)-8-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1]benzazepine [ No CAS ]
  • [ 3914-42-9 ]
  • 6-(4-chlorophenyl)-8-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4H-[1,2,4]triazolo[4,3-a][1]benzazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.4 g Example 48F Preparation of 6-(4-chlorophenyl)-8-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4H-[1,2,4]triazolo[4,3-a][1]benzazepine 75 mg of 6-(4-chlorophenyl)-8-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1]benzazepine were initially charged in 5.7 ml of THF. The solution was cooled to -60 C., and 0.40 ml of 1.4 M sec-butyllithium solution was added slowly under argon (time for the dropwise addition 1 min) The solution was stirred in the dark and at -67--60 C. for 1 h. 74 mg of <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (CAS 3914-42-9) in 1.3 ml of THF were added dropwise at -65 C. The cooling bath was removed, the mixture was stirred was at room temperature overnight and 3 ml of ammonium chloride solution were added. The mixture was extracted three times with ethyl acetate. The extract was dried over sodium sulphate and concentrated. This gave 110 mg of crude product which were purified by column chromatography on 10 g of silica gel using MeCl/EtOH 100/0-95/5. This gave 16 mg of product which were purified by RP-HPLC (column: X-Bridge C18 5 mum 100*30 mm, mobile phase: acetonitrile/water (0.1% by volume of formic acid) gradient, flow rate 50 ml/min, RT). This gave 2.4 mg of 6-(4-chlorophenyl)-8-(3,5-dimethyl-1,2-oxazol-4-yl)-1-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4H-[1,2,4]triazolo[4,3-a][1]benzazepine. 1H NMR (400 MHz, CDCl3): delta=2.21 (s, 3H), 2.36 (s, 3H), 2.56 (s, 3H), 2.66 (s, 3H), 3.64-3.77 (m, 1H), 3.86-3.99 (m, 2H), 6.19 (d, 1H), 7.13-7.17 (m, 3H), 7.31 (d, 2H), 7.43 (dd, 1H), 7.52 (d, 1H).
  • 20
  • 6-(4-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1]benzazepine [ No CAS ]
  • [ 3914-42-9 ]
  • 6-(4-chlorophenyl)-1-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4H-[1,2,4]triazolo[4,3-a][1]benzazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
9.2 g Example 39 Preparation of 6-(4-chlorophenyl)-1-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4H-[1,2,4]triazolo[4,3-a][1]benzazepine At -70 C., 36 ml of lithium hexamethyldisilazide solution (1M in toluene) were added slowly to a solution of 10.1 g of 6-(4-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1]benzazepine (Example 1C) in 1 l of THF. The mixture was stirred for 90 min at -70 C., and a solution of 4.35 g of <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (CAS 3914-42-9) in 15 ml of THF was then added dropwise. With warming to RT, the mixture was stirred for 16 hours. The reaction was added to saturated ammonium chloride solution and extracted three times with dichloromethane. The combined organic phases were washed with 50% brine and dried over sodium sulphate, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel (dichloromethane/methanol gradient). Yield: 9.2 g of 6-(4-chlorophenyl)-1-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4H-[1,2,4]triazolo[4,3-a][1]benzazepine. 1H NMR (300 MHz, DMSO-d6): delta=2.47 (s, 3H); about 2.50 (s, 3H, signal obscured by DMSO); 3.65-3.80 (m, 3H); 6.32 (d, 1H); 7.19-7.27 (m, 3H); 7.42 (d, 2H); 7.49 (dt, 1H); 7.62 (dt, 1H); 7.77 (d, 1H).
  • 21
  • [ 138091-52-8 ]
  • [ 3914-42-9 ]
  • tert-butyl 3-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In N,N-dimethyl-formamide; at 100℃; for 4h;Sealed tube; The title compound was obtained in analogy to example 35, intermediate b, from 2-(chloromethyl)-5-methyl-i,3,4-oxadiazole (CAS RN 3914-42-9) and and tert-butyl 4-oxo-i-phenyl- 1,3 ,8-triazaspiro [4.51 decane- 8-carboxylate (example 35, intermediate c) without addition of TEA at 60C over 75 minutes as a colorless solid. MS (El): mlz = 427.227 [M]; A suspension of tert-butyl 4-oxo- 1 -phenyl- 1,3,8 -triazaspiro [4.5] decane- 8-carboxylate (249 mg,751 j.imol), 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (126 mg, 751 imol; CASRN 78667-04-6) and TEA (314 iL, 2.25 mmol) in DMF (2 mL) were stirred at RT overnight. After 16 hours, NaH (55% in mineral oil, 72.1 mg, 1.65 mmol; CAS RN 7646-69-7) was added. The reaction mixture was heated to 100C in a sealed tube over 4 hours. The reaction mixture was poured on half-saturated aqueous NH4C1 solution and EtOAc and the layers were separated.The aqueous layer was extracted once with EtOAc. The organic layers were washed twice with H20 and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 12 g column using an MPLC system eluting with a gradient of n-heptane : EtOAc (100 : 0 to 0: 100) to give the title compound as acolorless foam (0.184 g; 57.6%).
  • 22
  • methyl 1-[3-[2-hydroxy-5-(trifluoromethyl)phenyl]phenyl]azetidine-3-carboxylate [ No CAS ]
  • [ 3914-42-9 ]
  • C22H20F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide; In acetonitrile; at 60℃; 33 mg of 2-(chloromethyl)-5-methyl-1,3,4-ox- adizaole (0.20 mmol; 1. leq) 4 mg of KI (0.02 mmoll 0.1 eq) and 80 mf of K2C03 (0.57 mmol; 2.5 eq) were introduced into a USP 16x100 tube. A solution of 80 mg of methyl 1 -[3-[2-hydroxy-5-(trifluoromethyl)phenyl] -phenyl]azetidine-3-carboxylate (preparation 124; 0.228 mmol; 1 eq) in 1 .5 mE of acetonitrile was added, and the reaction mixture was stirred on a l3ohdan block overnight at 60 C. The solvent was evaporated off under a nitrogen stream, then the residue was diluted with 1 mE of watet 0.5 mE of 1 M HC1 was added, then the aqueous phase was extracted with EtOAc. The organic phase was filtered on a hydrophobic membrane rinsed woth 1 mE of EtOAc, then dried under a nitrogen stream and on a Genevac for 15 h at 30 C. The residue was purified by EC-MS-prep (Euna C18, 50x250 mm 10 pm column (Phenomenex); Mobile phase H20/ acetonitrile) to give 24 mg of the title compound. Yld: 24%.
  • 23
  • tert-butyl N-[(3R)-1-[1-(4-cyanophenyl)-5-hydroxy-pyrazole-3-carbonyl]-3-piperidyl]carbamate [ No CAS ]
  • [ 3914-42-9 ]
  • C25H29N7O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; for 1h;Heating; General procedure: To a stirred suspension of10(30 mg, 0.07 mmol) and potassium carbonate (20 mg, 0.15 mmol) in DMF (500 muL) was added 2-bromoacetamide (15 mg, 0.11 mmol) and the mixture heated to 80 C for 1 h. The reaction mixture was concentrated to dryness and 4 MHCl/dioxane (1 mL) added. After concentrating to dryness, the residue was purified by prepHPLC(high pH) to afford the title compound(8 mg, 30%) as a white powder.
  • 24
  • tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate [ No CAS ]
  • [ 3914-42-9 ]
  • tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)propanoate (Racemate) To a solution of 750 mg (2.00 mmol) of tert-butyl[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 15 ml of THF were added, under argon at -70 C., 2.50 ml (2.50 mmol, 1.25 eq.) of 1N lithium bis(trimethylsilyl)amide in THF and the mixture was stirred for 30 min. Subsequently, 273 mul (2.66 mmol, 1.33 eq.) of <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> were added and the mixture was stirred at -70 C. for 30 min and while coming to RT overnight. The reaction mixture was admixed with 10 ml of saturated aqueous ammonium chloride solution, 10 ml of water and 80 ml of ethyl acetate. The aqueous phase was extracted once with ethyl acetate and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried and concentrated. The crude product was then purified by means of Biotage-Isolera (eluent: cyclohexane/ethyl acetate, 20-75%). Yield: 448 mg (47% of theory). LC/MS [Method 1]: Rt=0.94 min; MS (ESIpos): m/z=471 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=7.98 (d, 1H), 7.75-7.69 (m, 2H), 7.51 (s, 1H), 6.52 (s, 1H), 5.43 (dd, 1H), 3.83-3.75 (m, 1H), 3.68-3.58 (m, 4H), 2.44 (s, 3H), 1.37 (s, 9H)
  • 25
  • [ 83-67-0 ]
  • [ 3914-42-9 ]
  • 3,7-dimethyl-1-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 120℃; for 3h; 2-Chloromethyl-5-methyl-1,3,4-oxadiazole (100 mg, 0.758 mmol), 3,7-dimethyl-1H-purine-2,6(3H,7H)-dione(136 mg, 0.758 mmol), potassium iodide (12.0 mg, 0.0758 mmol) and potassium carbonate (209 mg, 1.52 mmol) were dissolved in anhydrous N,N-dimethylformamide (3 mL). The reaction was heated to 120C and reacted for 3 hours. The reaction solution was cooled to 20C, filtered and purified by preparative HPLC to give 3,7-dimethyl-1-((5-methyl-1,3,4-oxadiazol-methyl)-1H-purine-2,6(3H,7H)-dione (30.0 mg) with a yield of 34%. 1H NMR: (400 MHz, Methonal-d4) delta 7.94(s, 1H), 5.39(s, 2H), 4.00(s, 3H), 3.57(s, 3H), 2.54(s, 3H). MS-ESI calcd. [M + H]+ 277, found 277.
  • 26
  • 6-(4-Fluorophenyl)-3-trityl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [ No CAS ]
  • [ 3914-42-9 ]
  • 6-(4-Fluorophenyl)-1-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-3-trityl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; To a solution of 6-(4-fluorophenyl)-3-trityl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (205 mg, 0.44 mmol) in DMF (4 mL) was added NaH (60% dispersion in mineral oil, 23 mg, 0.57 mmol) in one portion at room temperature. The reaction was stirred until gas evolution had ceased, then <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (58 muL, 0.57 mmol) was added. The mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with water and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (2X), dried over Na2SO4, filtered, and concentrated. The crude solid was purified (FCC, SiO2, 0 to 60% EtOAc in hexanes) to yield the title compound (129 mg, 52%) as a foam.1H NMR (500 MHz, CDCl3) delta 7.97 (d, J = 2.0 Hz, 1H), 7.57- 7.50 (m, 6H), 7.44- 7.36 (m, 2H), 7.34 (d, J = 2.0 Hz, 1H), 7.28- 7.26 (m, 1H), 7.26- 7.17 (m, 7H), 7.12- 7.05 (m, 2H), 5.21 (s, 2H), 2.49 (s, 3H).
  • 27
  • 4-(6-(3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride [ No CAS ]
  • [ 3914-42-9 ]
  • 6-(2-hydroxy-2-methylpropoxy)-4-(6-(6-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With caesium carbonate; In dimethyl sulfoxide; at 50℃; for 16h; A solution of 4-(6-(3 ,6-diazabicyclo[3. 1.1 ]heptan-3 -yl)pyridin-3 -yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (Intermediate P43; 20 mg, 0.0419 mmol) in DMSO (837.9 tL) was treated with C52CO3(s) (54.60 mg, 0.1676 mmol ) and <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (5.553 mg, 0.04189 mmol). The resulting mixture was stirred 16 h at 50 C. After cooling to ambient temperature, the reaction mixture was partitioned between DCM (1 mL) and water (5 mL), and then extracted with DCM (3 x 5 mL). The combined organic extracts were washed with brine (5 mL), then dried over anhydrous Na2SO4(), filtered and concentrated in vacuo. The crude residue was purified by silica chromatography (using 0-100% DCM in Hexane then 0-60% (2% NH4OHI2O% MeOHI78% DCM) in DCM as the gradient eluent) to afford the title compound (10.06 mg, 46% yield). MS (apci) m/z = 501.2 (M+H).
  • 28
  • 5-[4-(trifluoromethoxy)phenyl]-3H-1,3-benzoxazol-2-one [ No CAS ]
  • [ 3914-42-9 ]
  • C18H12F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.03 mg With potassium carbonate; In acetonitrile; at 20℃; for 16h; To the mixture of A-4 (200 mg, 0.68 mmol) and 2-(chloromethyl)-5 -methyl- 1,3, 4-oxadiazole (179.6 mg, 1.35 mmol) in ACN (3 mL) was added K2C03 (187.27 mg, 1.35 mmol) and the mixture was stirred at 20 C for 16 hours. The mixture was diluted with H20 (20 mL), and the mixture was extracted with EtOAc (20 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2SC>4, filtered and the filtrate was concentrated to give the crude product, which was purified by Prep-HPLC (Phenomenex Gemini (150 mm x 25mm,10 muiotaeta); A = H20 (0.05% NH4OH) and B = CH3CN); 58-68% B over 8 minutes) to afford Compound 51 (52.03 mg, 0.13 mmol) as a solid. XH NMR (MeOD-c 400MHz) deltaH = 7.70 (d, 2H), 7.52 (d, 1H), 7.48 - 7.44 (m, 1H), 7.40 - 7.34 (m, 3H), 5.40 (s, 2H), 2.52 (s, 3H). LCMS Rt = 1.18 min using Method A, MS ESI calcd. for Ci8Hi3F3N304 [M+H]+ 392.1, found 391.9.
  • 29
  • [ 790667-99-1 ]
  • [ 3914-42-9 ]
  • tert-butyl (2S,4S)-2-methyl-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% To a solution of tert-butyl (2S,4S)-4-hydroxy-2-methyl-piperidine-1-carboxylate (0.5 g, 2 mmol) in N,N-dimethylformamide (5 mL) under nitrogen at room temperature is added portionwise sodium tert-butoxide (0.92 g, 9.28 mmol). The resulting reaction mixture is stirred at room temperature for 40 min. The reaction mixture is cooled to 0 C. and <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (0.416 g, 3.14 mmol) is added. The resulting solution stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the residue diluted with water. The mixture is extracted with 3 portions of ethyl acetate. The combined organic extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude oil. The residue is taken up in dimethyl sulfoxide (to a total volume of 2 ml), and purified by prep-HPLC (Phenomenex Gemini-NX 10 Micron 30*100 mm C-18) (CH3CN & Water with 10 mM ammonium bicarbonate adjusted to pH 9 with ammonium hydroxide, 15% to 100% CH3CN over 7 min at 50 ml/min) (1 injection) (204 nm) to afford the title compound (0.028 g, 0.089 mmol, 4%). MS m/z 312.0 (M+H).
  • 30
  • [ 42869-47-6 ]
  • [ 3914-42-9 ]
  • 2-((6-bromo-2-methyl-1H-imidazo[4,5-b]pyridin-1-yl)methyl)-5-methyl-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.55 g With tetra-(n-butyl)ammonium iodide; potassium hydroxide; In tetrahydrofuran; at 60℃; for 2h; Potassium hydroxide (2.00 g) was added to a solution of 6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (5.80 g), <strong>[3914-42-9]<strong>[3914-42-9]2-(chloromethyl)-5-methyl-1,3,4-oxadiazol</strong>e</strong> (3.70 g) and TBAI (1.01 g) in THF (80 mL) at room temperature. The mixture was stirred at 60C for 2 hours. The mixture was poured into water at room temperature, and extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (methanol/ethyl acetate) to obtain the title compound (1.550 g). 1H NMR (300 MHz, DMSO-d6) delta 2.47 (3H, s), 2.61 (3H, s), 5.86 (2H, s), 8.36 (1H, d, J = 2.2 Hz), 8.44 (1H, d, J = 2.2 Hz).
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